synth-ai 0.2.9.dev0__py3-none-any.whl → 0.2.23.dev3__py3-none-any.whl

synth_ai/cli/task_apps.py

@@ -1,6 +1,8 @@
 from __future__ import annotations
 
+import argparse
 import ast
+import asyncio
 import contextlib
 import functools
 import hashlib
@@ -8,18 +10,112 @@ import importlib
 import importlib.util
 import inspect
 import os
-import signal
+import shlex
 import shutil
+import signal
 import subprocess
 import sys
 import tempfile
+import textwrap
+import time
+import types
+from collections.abc import Callable, Iterable, Iterator, Sequence
 from dataclasses import dataclass
+from datetime import UTC, datetime
 from pathlib import Path
-from typing import Callable, Iterable, Sequence
+from typing import Any, cast
+
+try:  # Python 3.11+
+    import tomllib as _toml
+except Exception:  # pragma: no cover - fallback
+    _toml = None  # type: ignore
 
 import click
-from synth_ai.task.apps import ModalDeploymentConfig, TaskAppConfig, TaskAppEntry, registry
-from synth_ai.task.server import run_task_app
+from click.exceptions import Abort
+from synth_ai.cli.commands.eval import core as eval_core
+from synth_ai.cli.commands.filter import core as filter_core
+
+# Tracing imports - make conditional for optional dependencies
+try:
+    from synth_ai.tracing_v3 import (  # type: ignore[import-untyped]
+        BaseEvent,
+        EnvironmentEvent,
+        RuntimeEvent,
+        SessionEventMarkovBlanketMessage,
+        SessionMessageContent,
+        SessionTimeStep,
+        SessionTracer,
+        TimeRecord,
+    )
+    from synth_ai.tracing_v3 import (  # type: ignore[import-untyped]
+        SessionTrace as V3SessionTrace,
+    )
+    _TRACING_AVAILABLE = True
+except (ImportError, ModuleNotFoundError, TypeError):
+    # Tracing system not available (missing optional dependencies)
+    BaseEvent = EnvironmentEvent = RuntimeEvent = None  # type: ignore
+    SessionEventMarkovBlanketMessage = SessionMessageContent = None  # type: ignore
+    SessionTimeStep = SessionTracer = TimeRecord = None  # type: ignore
+    V3SessionTrace = None  # type: ignore
+    _TRACING_AVAILABLE = False
+
+# ---------------------------------------------------------------------------
+# Dynamic imports to avoid hard dependencies during type checking.
+# ---------------------------------------------------------------------------
+ModalDeploymentConfigType = TaskAppConfigType = TaskAppEntryType = Any
+
+try:  # Resolve base URL defaults lazily
+    _config_module = cast(
+        Any, importlib.import_module("synth_ai.config.base_url")
+    )
+    PROD_BASE_URL_DEFAULT = cast(str, _config_module.PROD_BASE_URL_DEFAULT)
+except Exception:  # pragma: no cover - fallback
+    PROD_BASE_URL_DEFAULT = "https://agent-learning.onrender.com"
+
+try:
+    _task_apps_module = cast(Any, importlib.import_module("synth_ai.task.apps"))
+    ModalDeploymentConfig = cast(
+        type[ModalDeploymentConfigType], _task_apps_module.ModalDeploymentConfig
+    )
+    TaskAppConfig = cast(type[TaskAppConfigType], _task_apps_module.TaskAppConfig)
+    TaskAppEntry = cast(type[TaskAppEntryType], _task_apps_module.TaskAppEntry)
+    registry = _task_apps_module.registry
+except Exception as exc:  # pragma: no cover - critical dependency
+    raise RuntimeError("Unable to load task app registry") from exc
+
+try:
+    _task_server_module = cast(Any, importlib.import_module("synth_ai.task.server"))
+    create_task_app = cast(Callable[..., Any], _task_server_module.create_task_app)
+    run_task_app = cast(Callable[..., Any], _task_server_module.run_task_app)
+except Exception as exc:  # pragma: no cover - critical dependency
+    raise RuntimeError("Unable to load task app server utilities") from exc
+
+
+def _load_demo_directory() -> Path | None:
+    """Return the demo task apps directory if available."""
+
+    try:
+        module = cast(
+            Any, importlib.import_module("synth_ai.demos.demo_task_apps.core")
+        )
+        loader = cast(Callable[[], str | Path | None], module.load_demo_dir)
+        demo_dir = loader()
+        if isinstance(demo_dir, str | Path):
+            demo_path = Path(demo_dir)
+            if demo_path.exists():
+                return demo_path.resolve()
+    except Exception:
+        return None
+    return None
+
+
+def _maybe_import(name: str) -> Any:
+    """Safely import a module by name and return it, or None on failure."""
+
+    try:
+        return importlib.import_module(name)
+    except Exception:
+        return None
 
 REPO_ROOT = Path(__file__).resolve().parents[2]
 
@@ -42,6 +138,25 @@ DEFAULT_SEARCH_RELATIVE = (
 )
 
 
+def _pearson(xs: Sequence[float], ys: Sequence[float]) -> float | None:
+    if len(xs) != len(ys) or len(xs) < 2:
+        return None
+    mean_x = sum(xs) / len(xs)
+    mean_y = sum(ys) / len(ys)
+    num = 0.0
+    denom_x = 0.0
+    denom_y = 0.0
+    for x, y in zip(xs, ys, strict=False):
+        dx = x - mean_x
+        dy = y - mean_y
+        num += dx * dy
+        denom_x += dx * dx
+        denom_y += dy * dy
+    if denom_x <= 0 or denom_y <= 0:
+        return None
+    return num / (denom_x ** 0.5 * denom_y ** 0.5)
+
+
 @dataclass
 class AppChoice:
     app_id: str
@@ -50,12 +165,12 @@ class AppChoice:
     source: str
     description: str | None = None
     aliases: tuple[str, ...] = ()
-    entry: TaskAppEntry | None = None
-    entry_loader: Callable[[], TaskAppEntry] | None = None
+    entry: TaskAppEntryType | None = None
+    entry_loader: Callable[[], TaskAppEntryType] | None = None
     modal_script: Path | None = None
     lineno: int | None = None
 
-    def ensure_entry(self) -> TaskAppEntry:
+    def ensure_entry(self) -> TaskAppEntryType:
         if self.entry is not None:
             return self.entry
         if self.entry_loader is None:
@@ -65,18 +180,311 @@ class AppChoice:
         return entry
 
 
+@dataclass
+class JudgeSpec:
+    name: str
+    fn: Callable[..., Any]
+    kwargs: dict[str, Any]
+
+
+def _parse_datetime_for_trace(value: Any) -> datetime | None:
+    if isinstance(value, datetime):
+        return value if value.tzinfo else value.replace(tzinfo=UTC)
+    if isinstance(value, str):
+        value = value.replace("Z", "+00:00")
+        try:
+            dt = datetime.fromisoformat(value)
+        except ValueError:
+            try:
+                dt = datetime.fromtimestamp(float(value), tz=UTC)
+            except Exception:
+                return None
+        return dt if dt.tzinfo else dt.replace(tzinfo=UTC)
+    if isinstance(value, int | float):
+        return datetime.fromtimestamp(float(value), tz=UTC)
+    return None
+
+
+def _time_record_from_dict(payload: dict[str, Any] | None) -> TimeRecord:
+    payload = payload or {}
+    event_time = payload.get("event_time")
+    if not isinstance(event_time, int | float):
+        try:
+            event_time = float(event_time)
+        except Exception:
+            event_time = float(time.time())
+    message_time = payload.get("message_time")
+    if message_time is not None:
+        try:
+            message_time = int(message_time)
+        except Exception:
+            message_time = None
+    return TimeRecord(event_time=event_time, message_time=message_time)
+
+
+def _event_from_dict(payload: dict[str, Any]) -> BaseEvent:
+    base_kwargs = {
+        "system_instance_id": payload.get("system_instance_id", ""),
+        "time_record": _time_record_from_dict(payload.get("time_record")),
+        "metadata": payload.get("metadata") or {},
+        "event_metadata": payload.get("event_metadata"),
+    }
+    if "actions" in payload:
+        return RuntimeEvent(actions=payload.get("actions") or [], **base_kwargs)
+    if any(key in payload for key in ("reward", "terminated", "truncated")):
+        return EnvironmentEvent(
+            reward=float(payload.get("reward", 0.0) or 0.0),
+            terminated=bool(payload.get("terminated", False)),
+            truncated=bool(payload.get("truncated", False)),
+            system_state_before=payload.get("system_state_before"),
+            system_state_after=payload.get("system_state_after"),
+            **base_kwargs,
+        )
+    # Check for LM CAIS event fields
+    if any(key in payload for key in ("model_name", "provider", "call_records")):
+        from synth_ai.tracing_v3.abstractions import LMCAISEvent
+        # Note: call_records are left as dicts - the storage layer will handle serialization
+        call_records = payload.get("call_records") or []
+        return LMCAISEvent(
+            model_name=payload.get("model_name", ""),
+            provider=payload.get("provider", ""),
+            input_tokens=payload.get("input_tokens"),
+            output_tokens=payload.get("output_tokens"),
+            total_tokens=payload.get("total_tokens"),
+            cost_usd=payload.get("cost_usd"),
+            latency_ms=payload.get("latency_ms"),
+            span_id=payload.get("span_id"),
+            trace_id=payload.get("trace_id"),
+            call_records=call_records,
+            **base_kwargs,
+        )
+    return BaseEvent(**base_kwargs)
+
+
+def _markov_message_from_dict(payload: dict[str, Any]) -> SessionEventMarkovBlanketMessage:
+    content_payload = payload.get("content") or {}
+    content = SessionMessageContent(
+        text=content_payload.get("text"),
+        json_payload=content_payload.get("json_payload"),
+    )
+    raw_type = (payload.get("message_type") or "").lower()
+    original_type = payload.get("message_type") or raw_type
+    
+    if raw_type in ("observation", "policy_system_prompt"):
+        normalized_type = "system"
+    elif raw_type in ("action", "policy_tool_call"):
+        normalized_type = "assistant"
+    elif raw_type in {"user", "assistant", "system", "tool_use", "tool_result"}:
+        normalized_type = raw_type
+    else:
+        normalized_type = "system"
+
+    metadata = dict(payload.get("metadata") or {})
+    metadata["original_message_type"] = original_type
+
+    return SessionEventMarkovBlanketMessage(
+        content=content,
+        message_type=normalized_type,
+        time_record=_time_record_from_dict(payload.get("time_record")),
+        metadata=metadata,
+    )
+
+
+def _step_from_dict(payload: dict[str, Any]) -> SessionTimeStep:
+    events = [
+        _event_from_dict(event)
+        for event in payload.get("events", [])
+        if isinstance(event, dict)
+    ]
+    messages = [
+        _markov_message_from_dict(msg)
+        for msg in payload.get("markov_blanket_messages", [])
+        if isinstance(msg, dict)
+    ]
+    timestamp = _parse_datetime_for_trace(payload.get("timestamp")) or datetime.now(UTC)
+    completed_at = _parse_datetime_for_trace(payload.get("completed_at"))
+    return SessionTimeStep(
+        step_id=payload.get("step_id", ""),
+        step_index=int(payload.get("step_index", 0) or 0),
+        timestamp=timestamp,
+        turn_number=payload.get("turn_number"),
+        events=events,
+        markov_blanket_messages=messages,
+        step_metadata=payload.get("step_metadata") or {},
+        completed_at=completed_at,
+    )
+
+
+def _session_trace_from_dict(payload: dict[str, Any]) -> V3SessionTrace | None:
+    if not isinstance(payload, dict):
+        return None
+    steps = [
+        _step_from_dict(step)
+        for step in payload.get("session_time_steps", [])
+        if isinstance(step, dict)
+    ]
+    events = [
+        _event_from_dict(event)
+        for event in payload.get("event_history", [])
+        if isinstance(event, dict)
+    ]
+    markov_history = [
+        _markov_message_from_dict(msg)
+        for msg in payload.get("markov_blanket_message_history", [])
+        if isinstance(msg, dict)
+    ]
+    created_at = _parse_datetime_for_trace(payload.get("created_at")) or datetime.now(UTC)
+    metadata = payload.get("metadata") or {}
+    session_metadata = payload.get("session_metadata")
+    return V3SessionTrace(
+        session_id=payload.get("session_id", ""),
+        created_at=created_at,
+        session_time_steps=steps,
+        event_history=events,
+        markov_blanket_message_history=markov_history,
+        metadata=metadata,
+        session_metadata=session_metadata,
+    )
+
+
+async def _store_trace(
+    tracer: SessionTracer | None,
+    trace_namespace: dict[str, Any] | None,
+    extra_metadata: dict[str, Any] | None = None,
+):
+    import logging
+    _logger = logging.getLogger(__name__)
+    
+    _logger.info(f"[STORE_TRACE_DEBUG] Called with tracer={tracer is not None}, trace_namespace={trace_namespace is not None}")
+    
+    if tracer is None or not isinstance(trace_namespace, dict):
+        _logger.warning(f"[STORE_TRACE_DEBUG] Early return: tracer={tracer is not None}, trace_namespace type={type(trace_namespace)}")
+        return
+    
+    _logger.info(f"[STORE_TRACE_DEBUG] trace_namespace keys: {list(trace_namespace.keys())}")
+    
+    # Handle both formats:
+    # - With session_trace key: {"session_trace": {...}}
+    # - Without session_trace key (trace itself is the session): {"session_id": ..., "markov_blanket_message_history": ...}
+    session_payload = trace_namespace.get("session_trace")
+    if not isinstance(session_payload, dict):
+        # If no session_trace key, assume "full" format where trace itself is the session_trace
+        if "session_id" in trace_namespace:
+            session_payload = trace_namespace
+            _logger.info("[STORE_TRACE_DEBUG] Using trace_namespace directly as session_payload (no session_trace key)")
+        else:
+            _logger.warning(f"[STORE_TRACE_DEBUG] No session_trace found or wrong type: {type(session_payload)}")
+            return
+    
+    _logger.info(f"[STORE_TRACE_DEBUG] session_payload keys: {list(session_payload.keys())}")
+    msg_count = len(session_payload.get("markov_blanket_message_history", []))
+    _logger.info(f"[STORE_TRACE_DEBUG] Found {msg_count} messages in session_payload")
+    
+    trace_obj = _session_trace_from_dict(session_payload)
+    if trace_obj is None:
+        _logger.warning("[STORE_TRACE_DEBUG] _session_trace_from_dict returned None")
+        return
+    
+    _logger.info(f"[STORE_TRACE_DEBUG] Created SessionTrace object with {len(trace_obj.markov_blanket_message_history)} messages")
+    
+    if tracer.db is None:
+        await tracer.initialize()
+    meta = dict(trace_obj.metadata or {})
+    if extra_metadata:
+        meta.update(extra_metadata)
+    trace_obj.metadata = meta
+    
+    _logger.info(f"[STORE_TRACE_DEBUG] Calling insert_session_trace for session_id={trace_obj.session_id}")
+    await tracer.db.insert_session_trace(trace_obj)
+    _logger.info("[STORE_TRACE_DEBUG] Successfully inserted trace")
+
+def _temporary_sys_path(paths: Sequence[Path]):
+    """Context manager to prepend entries to sys.path temporarily."""
+
+    @contextlib.contextmanager
+    def _manager() -> Iterator[None]:
+        added: list[str] = []
+        for p in paths:
+            try:
+                resolved = str(p.resolve())
+            except Exception:
+                continue
+            if resolved in sys.path:
+                continue
+            sys.path.insert(0, resolved)
+            added.append(resolved)
+        try:
+            yield None
+        finally:
+            for entry in added:
+                with contextlib.suppress(ValueError):
+                    sys.path.remove(entry)
+
+    return _manager()
+
+
+def _possible_module_names(
+    path: Path, module_search_roots: Sequence[Path]
+) -> list[tuple[str, Path]]:
+    """Return potential module names based on candidate roots."""
+
+    candidates: list[tuple[str, Path]] = []
+    for root in module_search_roots:
+        try:
+            resolved_root = root.resolve()
+        except Exception:
+            continue
+        if not resolved_root.exists() or not path.is_relative_to(resolved_root):
+            continue
+        relative = path.relative_to(resolved_root)
+        stem = relative.with_suffix("")
+        parts = list(stem.parts)
+        if not parts:
+            continue
+        module_name = ".".join(parts)
+        if module_name:
+            candidates.append((module_name, resolved_root))
+    return candidates
+
+
+def _ensure_parent_namespace(module_name: str, search_root: Path) -> None:
+    """Ensure namespace packages exist for dotted module names."""
+
+    parts = module_name.split(".")
+    for depth in range(1, len(parts)):
+        parent_name = ".".join(parts[:depth])
+        if parent_name in sys.modules:
+            continue
+        parent_module = types.ModuleType(parent_name)
+        candidate_dir = search_root.joinpath(*parts[:depth])
+        try:
+            resolved = candidate_dir.resolve()
+        except Exception:
+            resolved = search_root.resolve()
+        parent_module.__path__ = [str(resolved)]  # type: ignore[attr-defined]
+        sys.modules[parent_name] = parent_module
+
+
 def _should_ignore_path(path: Path) -> bool:
     return any(part in DEFAULT_IGNORE_DIRS for part in path.parts)
 
 
 def _candidate_search_roots() -> list[Path]:
+    """Only search for task apps in the current working directory and subdirectories."""
     roots: list[Path] = []
+
+    demo_path = _load_demo_directory()
+    if demo_path is not None and demo_path.is_dir():
+        roots.append(demo_path)
+
+    # Allow explicit search paths via environment variable
     env_paths = os.environ.get("SYNTH_TASK_APP_SEARCH_PATH")
     if env_paths:
         for chunk in env_paths.split(os.pathsep):
             if chunk:
                 roots.append(Path(chunk).expanduser())
 
+    # Always include current working directory
     cwd = Path.cwd().resolve()
     roots.append(cwd)
 
@@ -86,16 +494,8 @@ def _candidate_search_roots() -> list[Path]:
         except Exception:
             continue
         roots.append(candidate)
-        if REPO_ROOT not in (None, candidate):
-            try:
-                repo_candidate = (REPO_ROOT / rel).resolve()
-            except Exception:
-                repo_candidate = None
-            if repo_candidate:
-                roots.append(repo_candidate)
-
-    roots.append(REPO_ROOT)
 
+    # Remove duplicates while preserving order
     seen: set[Path] = set()
     ordered: list[Path] = []
     for root in roots:
@@ -119,21 +519,27 @@ class _TaskAppConfigVisitor(ast.NodeVisitor):
             app_id = _extract_app_id(node)
             if app_id:
                 self.matches.append((app_id, getattr(node, "lineno", 0)))
+        elif _is_register_task_app_call(node):
+            app_id = _extract_register_app_id(node)
+            if app_id:
+                self.matches.append((app_id, getattr(node, "lineno", 0)))
         self.generic_visit(node)
 
 
 def _is_task_app_config_call(node: ast.Call) -> bool:
     func = node.func
-    if isinstance(func, ast.Name) and func.id == "TaskAppConfig":
-        return True
-    if isinstance(func, ast.Attribute) and func.attr == "TaskAppConfig":
-        return True
-    return False
+    return (isinstance(func, ast.Name) and func.id == "TaskAppConfig") or (
+        isinstance(func, ast.Attribute) and func.attr == "TaskAppConfig"
+    )
 
 
 def _extract_app_id(node: ast.Call) -> str | None:
     for kw in node.keywords:
-        if kw.arg == "app_id" and isinstance(kw.value, ast.Constant) and isinstance(kw.value.value, str):
+        if (
+            kw.arg == "app_id"
+            and isinstance(kw.value, ast.Constant)
+            and isinstance(kw.value.value, str)
+        ):
             return kw.value.value
     if node.args:
         first = node.args[0]
@@ -142,6 +548,29 @@ def _extract_app_id(node: ast.Call) -> str | None:
     return None
 
 
+def _is_register_task_app_call(node: ast.Call) -> bool:
+    func = node.func
+    return (isinstance(func, ast.Name) and func.id == "register_task_app") or (
+        isinstance(func, ast.Attribute) and func.attr == "register_task_app"
+    )
+
+
+def _extract_register_app_id(node: ast.Call) -> str | None:
+    # Look for entry=TaskAppEntry(app_id="...", ...)
+    for kw in node.keywords:
+        if kw.arg == "entry" and isinstance(kw.value, ast.Call):
+            entry_call = kw.value
+            if isinstance(entry_call.func, ast.Name) and entry_call.func.id == "TaskAppEntry":
+                for entry_kw in entry_call.keywords:
+                    if (
+                        entry_kw.arg == "app_id"
+                        and isinstance(entry_kw.value, ast.Constant)
+                        and isinstance(entry_kw.value.value, str)
+                    ):
+                        return entry_kw.value.value
+    return None
+
+
 class _ModalAppVisitor(ast.NodeVisitor):
     def __init__(self) -> None:
         self.app_aliases: set[str] = set()
@@ -168,7 +597,11 @@ class _ModalAppVisitor(ast.NodeVisitor):
             if name:
                 self.matches.append((name, getattr(node, "lineno", 0)))
         elif isinstance(func, ast.Attribute):
-            if isinstance(func.value, ast.Name) and func.value.id in self.modal_aliases and func.attr == "App":
+            if (
+                isinstance(func.value, ast.Name)
+                and func.value.id in self.modal_aliases
+                and func.attr == "App"
+            ):
                 name = _extract_modal_app_name(node)
                 if name:
                     self.matches.append((name, getattr(node, "lineno", 0)))
@@ -177,7 +610,11 @@ class _ModalAppVisitor(ast.NodeVisitor):
 
 def _extract_modal_app_name(node: ast.Call) -> str | None:
     for kw in node.keywords:
-        if kw.arg in {"name", "app_name"} and isinstance(kw.value, ast.Constant) and isinstance(kw.value.value, str):
+        if (
+            kw.arg in {"name", "app_name"}
+            and isinstance(kw.value, ast.Constant)
+            and isinstance(kw.value.value, str)
+        ):
             return kw.value.value
     if node.args:
         first = node.args[0]
@@ -186,12 +623,14 @@ def _extract_modal_app_name(node: ast.Call) -> str | None:
     return None
 
 
-@functools.lru_cache(maxsize=1)
 def _collect_task_app_choices() -> list[AppChoice]:
+    # Clear registry to avoid duplicate registration errors
+    registry.clear()
+
     choices: list[AppChoice] = []
     with contextlib.suppress(Exception):
-        import synth_ai.demos.demo_task_apps  # noqa: F401
-    choices.extend(_collect_registered_choices())
+        _maybe_import("synth_ai.demos.demo_task_apps")
+    # Only use discovered task apps, not registered ones (since we moved them to examples)
     choices.extend(_collect_scanned_task_configs())
     choices.extend(_collect_modal_scripts())
 
@@ -210,6 +649,7 @@ def _collect_task_app_choices() -> list[AppChoice]:
             continue
         unique[key] = choice
         ordered.append(choice)
+    ordered.sort(key=_app_choice_sort_key)
     return ordered
 
 
@@ -240,6 +680,10 @@ def _collect_scanned_task_configs() -> list[AppChoice]:
     results: list[AppChoice] = []
     seen: set[tuple[str, Path]] = set()
     for root in _candidate_search_roots():
+        try:
+            root_resolved = root.resolve()
+        except Exception:
+            continue
         if not root.exists() or not root.is_dir():
             continue
         for path in root.rglob("*.py"):
@@ -269,7 +713,11 @@ def _collect_scanned_task_configs() -> list[AppChoice]:
                         path=path.resolve(),
                         source="discovered",
                         description=f"TaskAppConfig in {path.name} (line {lineno})",
-                        entry_loader=lambda p=path.resolve(), a=app_id: _load_entry_from_path(p, a),
+                        entry_loader=lambda p=path.resolve(),
+                        a=app_id,
+                        roots=(root_resolved,): _load_entry_from_path(
+                            p, a, module_search_roots=roots
+                        ),
                         lineno=lineno,
                     )
                 )
@@ -316,15 +764,60 @@ def _collect_modal_scripts() -> list[AppChoice]:
     return results
 
 
+def _app_choice_sort_key(choice: AppChoice) -> tuple[int, int, int, int, int, str, str]:
+    """Ranking heuristic so wrapper-style task apps surface first."""
+
+    # Prioritize apps in the current working directory (demo or otherwise)
+    cwd_rank = 1
+    try:
+        cwd = Path.cwd().resolve()
+        if choice.path.is_relative_to(cwd):
+            # Check if this is directly in CWD (not in subdirectories like examples/)
+            try:
+                rel_path = choice.path.relative_to(cwd)
+                # If it's in the immediate directory or one level deep, prioritize it
+                if len(rel_path.parts) <= 2:
+                    cwd_rank = 0
+            except Exception:
+                pass
+    except Exception:
+        pass
+
+    # Further prioritize apps in the demo directory if one is set
+    demo_rank = 1
+    demo_dir = _load_demo_directory()
+    if demo_dir and choice.path.is_relative_to(demo_dir):
+        demo_rank = 0
+
+    modal_rank = 1 if choice.modal_script else 0
+
+    name = choice.path.name.lower()
+    file_rank = 3
+    if name.endswith("_task_app.py") or name.endswith("task_app.py"):
+        file_rank = 0
+    elif name.endswith("_app.py") or "task_app" in name:
+        file_rank = 1
+    elif name.endswith(".py"):
+        file_rank = 2
+
+    directory_rank = 0 if choice.path.parent.name.lower() in {"task_app", "task_apps"} else 1
+
+    return (
+        demo_rank,
+        cwd_rank,
+        modal_rank,
+        file_rank,
+        directory_rank,
+        choice.app_id,
+        str(choice.path),
+    )
+
+
 def _choice_matches_identifier(choice: AppChoice, identifier: str) -> bool:
     ident = identifier.strip()
     if not ident:
         return False
-    if ident == choice.app_id or ident == choice.label:
-        return True
-    if ident in choice.aliases:
-        return True
-    return False
+    return ident == choice.app_id or ident == choice.label or ident in choice.aliases
 
 
 def _choice_has_modal_support(choice: AppChoice) -> bool:
@@ -333,10 +826,128 @@ def _choice_has_modal_support(choice: AppChoice) -> bool:
     try:
         entry = choice.ensure_entry()
     except click.ClickException:
-        return False
+        # If we can't load the entry, try to detect Modal support via AST parsing
+        return _has_modal_support_in_file(choice.path)
     return entry.modal is not None
 
 
+def _has_modal_support_in_file(path: Path) -> bool:
+    """Detect if a file has Modal deployment support by parsing the AST."""
+    try:
+        source = path.read_text(encoding="utf-8")
+        tree = ast.parse(source, filename=str(path))
+
+        # Look for ModalDeploymentConfig in register_task_app calls
+        for node in ast.walk(tree):
+            if isinstance(node, ast.Call) and _is_register_task_app_call(node):
+                # Check if the entry has modal=ModalDeploymentConfig(...)
+                for kw in node.keywords:
+                    if kw.arg == "entry" and isinstance(kw.value, ast.Call):
+                        entry_call = kw.value
+                        if (
+                            isinstance(entry_call.func, ast.Name)
+                            and entry_call.func.id == "TaskAppEntry"
+                        ):
+                            for entry_kw in entry_call.keywords:
+                                if entry_kw.arg == "modal" and isinstance(entry_kw.value, ast.Call):
+                                    modal_call = entry_kw.value
+                                    if (
+                                        isinstance(modal_call.func, ast.Name)
+                                        and modal_call.func.id == "ModalDeploymentConfig"
+                                    ):
+                                        return True
+    except Exception:
+        pass
+    return False
+
+
+def _extract_modal_config_from_file(path: Path) -> ModalDeploymentConfigType | None:
+    """Extract ModalDeploymentConfig from a file by parsing the AST."""
+    try:
+        source = path.read_text(encoding="utf-8")
+        tree = ast.parse(source, filename=str(path))
+
+        # Look for ModalDeploymentConfig in register_task_app calls
+        for node in ast.walk(tree):
+            if isinstance(node, ast.Call) and _is_register_task_app_call(node):
+                # Check if the entry has modal=ModalDeploymentConfig(...)
+                for kw in node.keywords:
+                    if kw.arg == "entry" and isinstance(kw.value, ast.Call):
+                        entry_call = kw.value
+                        if (
+                            isinstance(entry_call.func, ast.Name)
+                            and entry_call.func.id == "TaskAppEntry"
+                        ):
+                            for entry_kw in entry_call.keywords:
+                                if entry_kw.arg == "modal" and isinstance(entry_kw.value, ast.Call):
+                                    modal_call = entry_kw.value
+                                    if (
+                                        isinstance(modal_call.func, ast.Name)
+                                        and modal_call.func.id == "ModalDeploymentConfig"
+                                    ):
+                                        # Extract the arguments to ModalDeploymentConfig
+                                        return _build_modal_config_from_ast(modal_call)
+    except Exception:
+        pass
+    return None
+
+
+def _build_modal_config_from_ast(modal_call: ast.Call) -> ModalDeploymentConfigType | None:
+    """Build a ModalDeploymentConfig from an AST Call node."""
+    try:
+        # Extract keyword arguments
+        kwargs = {}
+        for kw in modal_call.keywords:
+            if kw.arg and isinstance(kw.value, ast.Constant):
+                kwargs[kw.arg] = kw.value.value
+            elif kw.arg == "pip_packages" and isinstance(kw.value, ast.List | ast.Tuple):
+                # Handle pip_packages list/tuple
+                packages: list[str] = []
+                value_node = kw.value
+                if isinstance(value_node, ast.List | ast.Tuple):
+                    for elt in value_node.elts:
+                        if isinstance(elt, ast.Constant):
+                            packages.append(elt.value)
+                kwargs[kw.arg] = tuple(packages)
+            elif kw.arg == "extra_local_dirs" and isinstance(kw.value, ast.List | ast.Tuple):
+                # Handle extra_local_dirs list/tuple of tuples
+                dirs = []
+                value_node = kw.value
+                if isinstance(value_node, ast.List | ast.Tuple):
+                    for elt in value_node.elts:
+                        if isinstance(elt, ast.List | ast.Tuple) and len(elt.elts) == 2:
+                            src = elt.elts[0].value if isinstance(elt.elts[0], ast.Constant) else None
+                            dst = elt.elts[1].value if isinstance(elt.elts[1], ast.Constant) else None
+                            if src and dst:
+                                dirs.append((src, dst))
+                kwargs[kw.arg] = tuple(dirs)
+            elif kw.arg == "secret_names" and isinstance(kw.value, ast.List | ast.Tuple):
+                # Handle secret_names list/tuple
+                secrets = []
+                value_node = kw.value
+                if isinstance(value_node, ast.List | ast.Tuple):
+                    for elt in value_node.elts:
+                        if isinstance(elt, ast.Constant):
+                            secrets.append(elt.value)
+                kwargs[kw.arg] = tuple(secrets)
+            elif kw.arg == "volume_mounts" and isinstance(kw.value, ast.List | ast.Tuple):
+                # Handle volume_mounts list/tuple of tuples
+                mounts = []
+                value_node = kw.value
+                if isinstance(value_node, ast.List | ast.Tuple):
+                    for elt in value_node.elts:
+                        if isinstance(elt, ast.List | ast.Tuple) and len(elt.elts) == 2:
+                            name = elt.elts[0].value if isinstance(elt.elts[0], ast.Constant) else None
+                            mount = elt.elts[1].value if isinstance(elt.elts[1], ast.Constant) else None
+                            if name and mount:
+                                mounts.append((name, mount))
+                kwargs[kw.arg] = tuple(mounts)
+
+        return ModalDeploymentConfig(**kwargs)
+    except Exception:
+        return None
+
+
 def _choice_has_local_support(choice: AppChoice) -> bool:
     if choice.modal_script:
         return False
@@ -349,20 +960,29 @@ def _choice_has_local_support(choice: AppChoice) -> bool:
 
 def _format_choice(choice: AppChoice, index: int | None = None) -> str:
     prefix = f"[{index}] " if index is not None else ""
-    rel_path: str
+    # Get file modification timestamp
     try:
-        rel_path = str(choice.path.relative_to(REPO_ROOT))
+        from datetime import datetime
+
+        mtime = choice.path.stat().st_mtime
+        modified_str = datetime.fromtimestamp(mtime).strftime("%Y-%m-%d %H:%M:%S")
+        details = f"Modified: {modified_str}"
     except Exception:
-        rel_path = str(choice.path)
-    details = choice.description or f"Located at {rel_path}"
-    return f"{prefix}{choice.app_id} ({choice.source}) – {details}"
+        # Fallback if timestamp unavailable
+        details = choice.description or "No timestamp available"
+    # Format: single line with timestamp
+    main_line = f"{prefix}{choice.app_id} ({choice.source}) – {details}"
+    return main_line
 
 
 def _prompt_user_for_choice(choices: list[AppChoice]) -> AppChoice:
     click.echo("Select a task app:")
     for idx, choice in enumerate(choices, start=1):
         click.echo(_format_choice(choice, idx))
-    response = click.prompt("Enter choice", default="1", type=str).strip() or "1"
+    try:
+        response = click.prompt("Enter choice", default="1", type=str).strip() or "1"
+    except (Abort, EOFError, KeyboardInterrupt) as exc:
+        raise click.ClickException("Task app selection cancelled by user") from exc
     if not response.isdigit():
         raise click.ClickException("Selection must be a number")
     index = int(response)
@@ -373,7 +993,7 @@ def _prompt_user_for_choice(choices: list[AppChoice]) -> AppChoice:
 
 def _select_app_choice(app_id: str | None, purpose: str) -> AppChoice:
     choices = _collect_task_app_choices()
-    if purpose == "serve":
+    if purpose in {"serve", "eval"}:
         filtered = [c for c in choices if not c.modal_script]
     elif purpose in {"deploy", "modal-serve"}:
         filtered = []
@@ -383,6 +1003,8 @@ def _select_app_choice(app_id: str | None, purpose: str) -> AppChoice:
     else:
         filtered = choices
 
+    filtered.sort(key=_app_choice_sort_key)
+
     if not filtered:
         raise click.ClickException("No task apps discovered for this command.")
 
@@ -391,6 +1013,9 @@ def _select_app_choice(app_id: str | None, purpose: str) -> AppChoice:
         if not matches:
             available = ", ".join(sorted({c.app_id for c in filtered}))
             raise click.ClickException(f"Task app '{app_id}' not found. Available: {available}")
+        exact_matches = [c for c in matches if c.app_id == app_id]
+        if len(exact_matches) == 1:
+            return exact_matches[0]
         if len(matches) == 1:
             return matches[0]
         # Prefer entries with modal support when required
@@ -410,21 +1035,160 @@ def _select_app_choice(app_id: str | None, purpose: str) -> AppChoice:
     return _prompt_user_for_choice(filtered)
 
 
-def _load_entry_from_path(path: Path, app_id: str) -> TaskAppEntry:
-    resolved = path.resolve()
-    module_name = f"_synth_task_app_{hashlib.md5(str(resolved).encode(), usedforsecurity=False).hexdigest()}"
+def _import_task_app_module(
+    resolved: Path,
+    module_name: str,
+    *,
+    namespace_root: Path | None,
+    sys_path_roots: Sequence[Path],
+    ensure_namespace: bool = True,
+) -> types.ModuleType:
     spec = importlib.util.spec_from_file_location(module_name, str(resolved))
     if spec is None or spec.loader is None:
         raise click.ClickException(f"Unable to load Python module from {resolved}")
+
     module = importlib.util.module_from_spec(spec)
     sys.modules[module_name] = module
+
+    with _temporary_sys_path(sys_path_roots):
+        if ensure_namespace and namespace_root is not None and "." in module_name:
+            _ensure_parent_namespace(module_name, namespace_root)
+
+        # Clear registry before importing to avoid duplicate registration errors
+        registry.clear()
+
+        try:
+            spec.loader.exec_module(module)
+        except Exception:
+            # Remove partially-imported module to avoid reuse
+            sys.modules.pop(module_name, None)
+            raise
+
+    return module
+
+
+@contextlib.contextmanager
+def _safe_import_context() -> Iterator[None]:
+    """Guard module imports against argparse/uvicorn side effects."""
+
+    original_argv = sys.argv[:]
+    sys.argv = [original_argv[0]] if original_argv else ["python"]
+
+    parser_cls = argparse.ArgumentParser
+    old_parse_args = parser_cls.parse_args
+
+    def _parse_noargs(self, args=None, namespace=None):  # type: ignore[override]
+        if args is None:
+            args = []
+        if namespace is None:
+            namespace = argparse.Namespace()
+        try:
+            return old_parse_args(self, args, namespace)
+        except SystemExit:
+            return namespace
+
+    parser_cls.parse_args = _parse_noargs  # type: ignore[assignment]
+
+    uvicorn_run = None
+    run_task_app_orig = None
     try:
-        spec.loader.exec_module(module)
-    except Exception as exc:
-        raise click.ClickException(f"Failed to import {resolved}: {exc}") from exc
+        import uvicorn  # type: ignore
+
+        uvicorn_run = uvicorn.run
+        uvicorn.run = lambda *args, **kwargs: None  # type: ignore[assignment]
+    except Exception:
+        uvicorn_run = None
+
+    try:
+        _task_server_patch = cast(
+            Any, importlib.import_module("synth_ai.task.server")
+        )
+        run_task_app_orig = cast(Callable[..., Any], _task_server_patch.run_task_app)
+        _task_server_patch.run_task_app = (  # type: ignore[assignment]
+            lambda *args, **kwargs: None
+        )
+    except Exception:
+        run_task_app_orig = None
+
+    try:
+        yield
+    finally:
+        sys.argv = original_argv
+        parser_cls.parse_args = old_parse_args  # type: ignore[assignment]
+        if uvicorn_run is not None:
+            try:
+                import uvicorn  # type: ignore
+
+                uvicorn.run = uvicorn_run  # type: ignore[assignment]
+            except Exception:
+                pass
+        if run_task_app_orig is not None:
+            try:
+                _task_server_patch = cast(
+                    Any, importlib.import_module("synth_ai.task.server")
+                )
+                _task_server_patch.run_task_app = run_task_app_orig  # type: ignore[assignment]
+            except Exception:
+                pass
+
+
+def _load_entry_from_path(
+    path: Path, app_id: str, module_search_roots: Sequence[Path] | None = None
+) -> TaskAppEntryType:
+    resolved = path.resolve()
+    search_roots: list[Path] = []
+    seen_roots: set[Path] = set()
+
+    def _append_root(candidate: Path) -> None:
+        try:
+            resolved_root = candidate.resolve()
+        except Exception:
+            return
+        if resolved_root in seen_roots:
+            return
+        seen_roots.add(resolved_root)
+        search_roots.append(resolved_root)
+
+    for root in module_search_roots or []:
+        _append_root(root)
+    _append_root(resolved.parent)
+    _append_root(REPO_ROOT)
+
+    last_error: Exception | None = None
+    module: types.ModuleType | None = None
+
+    for module_name, namespace_root in _possible_module_names(resolved, search_roots):
+        try:
+            with _safe_import_context():
+                module = _import_task_app_module(
+                    resolved,
+                    module_name,
+                    namespace_root=namespace_root,
+                    sys_path_roots=search_roots,
+                    ensure_namespace=True,
+                )
+            break
+        except Exception as exc:  # pragma: no cover - best-effort fallbacks
+            last_error = exc
+            continue
+
+    if module is None:
+        hashed_name = f"_synth_task_app_{hashlib.md5(str(resolved).encode(), usedforsecurity=False).hexdigest()}"
+        try:
+            with _safe_import_context():
+                module = _import_task_app_module(
+                    resolved,
+                    hashed_name,
+                    namespace_root=None,
+                    sys_path_roots=search_roots,
+                    ensure_namespace=False,
+                )
+        except Exception as exc:  # pragma: no cover - propagate meaningful error
+            detail = last_error or exc
+            raise click.ClickException(f"Failed to import {resolved}: {detail}") from detail
 
-    config_obj: TaskAppConfig | None = None
-    factory_callable: Callable[[], TaskAppConfig] | None = None
+    config_obj: TaskAppConfigType | None = None
+    factory_callable: Callable[[], TaskAppConfigType] | None = None
 
     for attr_name in dir(module):
         try:
@@ -433,7 +1197,11 @@ def _load_entry_from_path(path: Path, app_id: str) -> TaskAppEntry:
             continue
         if isinstance(attr, TaskAppConfig) and attr.app_id == app_id:
             config_obj = attr
-            factory_callable = lambda cfg=attr: cfg
+
+            def _return_config(cfg: TaskAppConfigType = attr) -> TaskAppConfigType:
+                return cfg
+
+            factory_callable = _return_config
             break
 
     if factory_callable is None:
@@ -452,28 +1220,47 @@ def _load_entry_from_path(path: Path, app_id: str) -> TaskAppEntry:
                 continue
             has_required = False
             for param in sig.parameters.values():
-                if param.kind in (inspect.Parameter.POSITIONAL_ONLY, inspect.Parameter.POSITIONAL_OR_KEYWORD) and param.default is inspect._empty:
+                if (
+                    param.kind
+                    in (inspect.Parameter.POSITIONAL_ONLY, inspect.Parameter.POSITIONAL_OR_KEYWORD)
+                    and param.default is inspect._empty
+                ):
                     has_required = True
                     break
             if has_required:
                 continue
             try:
-                result = attr()
+                with _safe_import_context():
+                    result = attr()
+            except SystemExit:
+                continue
             except Exception:
                 continue
             if isinstance(result, TaskAppConfig) and result.app_id == app_id:
-                def _factory() -> TaskAppConfig:
-                    return attr()  # type: ignore[call-arg]
-                factory_callable = _factory
+                # Bind attr to a local and close over it without exposing parameters
+                bound_func: Callable[[], TaskAppConfig] = cast(Callable[[], TaskAppConfig], attr)  # type: ignore[assignment]
+
+                def _factory_noargs(
+                    func: Callable[[], TaskAppConfigType] = bound_func,
+                ) -> TaskAppConfigType:
+                    return func()
+
+                factory_callable = _factory_noargs
                 config_obj = result
                 break
 
+    # If no TaskAppConfig found directly, check if it was registered via register_task_app
     if factory_callable is None or config_obj is None:
-        raise click.ClickException(
-            f"Could not locate TaskAppConfig for '{app_id}' in {resolved}."
-        )
-
-    modal_cfg: ModalDeploymentConfig | None = None
+        try:
+            # Check if the app was registered in the registry
+            entry = registry.get(app_id)
+            return entry
+        except KeyError as exc:
+            raise click.ClickException(
+                f"Could not locate TaskAppConfig for '{app_id}' in {resolved}."
+            ) from exc
+
+    modal_cfg: ModalDeploymentConfigType | None = None
     for attr_name in dir(module):
         try:
             attr = getattr(module, attr_name)
@@ -483,6 +1270,10 @@ def _load_entry_from_path(path: Path, app_id: str) -> TaskAppEntry:
             modal_cfg = attr
             break
 
+    # If no ModalDeploymentConfig found, try to detect it via AST parsing
+    if modal_cfg is None:
+        modal_cfg = _extract_modal_config_from_file(resolved)
+
     description = inspect.getdoc(module) or f"Discovered task app in {resolved.name}"
     env_files: Iterable[str] = getattr(module, "ENV_FILES", ())  # type: ignore[arg-type]
 
@@ -507,20 +1298,283 @@ def _resolve_env_paths_for_script(script_path: Path, explicit: Sequence[str]) ->
             resolved.append(p)
         return resolved
 
+    # Always prompt for env file selection instead of auto-loading defaults
     script_dir = script_path.parent.resolve()
-    fallback_order = [
-        script_dir / ".env",
-        REPO_ROOT / "examples" / "rl" / ".env",
-        REPO_ROOT / "examples" / "warming_up_to_rl" / ".env",
-        REPO_ROOT / ".env",
-    ]
-    resolved = [p for p in fallback_order if p.exists()]
-    if resolved:
-        return resolved
-    created = _interactive_create_env(script_dir)
-    if created is None:
-        raise click.ClickException("Env file required (--env-file) for this task app")
-    return [created]
+    cwd = Path.cwd()
+
+    # Look for env files in current working directory first, then repo root
+    env_candidates = []
+
+    # Add CWD env files first (prioritized)
+    cwd_env_files = sorted(cwd.glob("**/*.env"))
+    env_candidates.extend(cwd_env_files)
+
+    # Add repo root env files
+    repo_env_files = sorted(REPO_ROOT.glob("**/*.env"))
+    # Avoid duplicates
+    for repo_file in repo_env_files:
+        if repo_file not in env_candidates:
+            env_candidates.append(repo_file)
+
+    if not env_candidates:
+        created = _interactive_create_env(script_dir)
+        if created is None:
+            raise click.ClickException("Env file required (--env-file) for this task app")
+        return [created]
+
+    click.echo("Select env file to load:")
+    for idx, path in enumerate(env_candidates, start=1):
+        click.echo(f"  {idx}) {path.resolve()}")
+    choice = click.prompt("Enter choice", type=click.IntRange(1, len(env_candidates)), default=1)
+    return [env_candidates[choice - 1]]
+
+
+def _path_is_within(child: Path, parent: Path) -> bool:
+    try:
+        child.resolve().relative_to(parent.resolve())
+        return True
+    except Exception:
+        return False
+
+
+@functools.lru_cache(maxsize=16)
+def _is_modal_shim(path_str: str) -> bool:
+    """Return True if the candidate CLI path refers to the synth-ai shim."""
+
+    path = Path(path_str)
+    try:
+        resolved = path.resolve(strict=True)
+    except Exception:
+        resolved = path
+
+    if not resolved.exists() or resolved.is_dir():
+        return False
+
+    snippet = ""
+    try:
+        snippet = resolved.read_bytes()[:4096].decode("utf-8", errors="ignore")
+    except Exception:
+        snippet = ""
+
+    shim_markers = (
+        "synth_ai.cli._modal_wrapper",
+        "from modal.__main__ import main",
+        "import modal.__main__",
+        "run_module('modal.__main__'",
+    )
+    if snippet and any(marker in snippet for marker in shim_markers):
+        return True
+
+    try:
+        size = resolved.stat().st_size
+    except Exception:
+        size = None
+
+    if (
+        size is not None
+        and size < 2048
+        and "python" in (snippet.splitlines() or [""])[0]
+        and (
+            "modal.__main__" in snippet
+            or "modal.__main__" in snippet.replace(" ", "")
+        )
+    ):
+        return True
+
+    virtual_env = os.environ.get("VIRTUAL_ENV")
+    if virtual_env and _path_is_within(resolved, Path(virtual_env)):
+        return True
+
+    if _path_is_within(resolved, REPO_ROOT):
+        return True
+
+    uv_tools_dir = Path.home() / ".local" / "share" / "uv" / "tools"
+    return uv_tools_dir.exists() and _path_is_within(resolved, uv_tools_dir)
+
+
+def _find_modal_executable(modal_cli: str) -> tuple[str | None, str | None]:
+    """Return the first non-shim executable and the first shim discovered on PATH."""
+
+    if not modal_cli:
+        modal_cli = "modal"
+
+    candidate_path = Path(modal_cli).expanduser()
+    if candidate_path.is_absolute() or len(candidate_path.parts) > 1:
+        resolved_candidate = candidate_path
+        if not resolved_candidate.is_absolute():
+            resolved_candidate = (Path.cwd() / resolved_candidate).resolve()
+        else:
+            resolved_candidate = resolved_candidate.resolve()
+        if not resolved_candidate.exists():
+            raise click.ClickException(f"--modal-cli path does not exist: {resolved_candidate}")
+        if not os.access(resolved_candidate, os.X_OK):
+            raise click.ClickException(f"--modal-cli is not executable: {resolved_candidate}")
+        return str(resolved_candidate), None
+
+    path_env = os.environ.get("PATH", "")
+    if not path_env:
+        return None, None
+
+    seen_dirs: set[str] = set()
+    seen_candidates: set[str] = set()
+    shim_path: str | None = None
+
+    for raw_entry in path_env.split(os.pathsep):
+        if not raw_entry:
+            continue
+        try:
+            resolved_entry = str(Path(raw_entry).resolve())
+        except Exception:
+            resolved_entry = os.path.normpath(raw_entry)
+        if resolved_entry in seen_dirs:
+            continue
+        seen_dirs.add(resolved_entry)
+
+        candidate = shutil.which(modal_cli, path=raw_entry)
+        if candidate is None:
+            continue
+        if candidate in seen_candidates:
+            continue
+        seen_candidates.add(candidate)
+
+        if _is_modal_shim(candidate):
+            if shim_path is None:
+                shim_path = candidate
+            continue
+        return candidate, shim_path
+
+    return None, shim_path
+
+
+def _modal_command_prefix(modal_cli: str) -> list[str]:
+    """Resolve a command prefix for invoking the Modal CLI within the active environment."""
+
+    force_wrapper_env = os.environ.get("SYNTH_FORCE_MODAL_WRAPPER", "").strip().lower()
+    if force_wrapper_env in {"1", "true", "yes"}:
+        click.secho(
+            "[modal-prefix] SYNTH_FORCE_MODAL_WRAPPER=1 -> using in-process wrapper",
+            fg="yellow",
+        )
+        return [sys.executable, "-m", "synth_ai.cli._modal_wrapper"]
+
+    lookup = modal_cli or "modal"
+    spec = importlib.util.find_spec("modal") if lookup == "modal" else None
+
+    preferred, shim_candidate = _find_modal_executable(lookup)
+    if preferred is not None:
+        detail = f"[modal-prefix] modal_cli={lookup} selected={preferred}"
+        if lookup == "modal":
+            detail += f" spec={'yes' if spec else 'no'}"
+        click.secho(detail, fg="cyan")
+        return [preferred]
+
+    if lookup != "modal":
+        raise click.ClickException(f"Modal CLI not found (looked for '{lookup}')")
+
+    if spec is not None:
+        warning = "[modal-prefix] Using synth-ai modal shim; pass --modal-cli /path/to/modal to override."
+        if shim_candidate is not None:
+            warning = (
+                f"[modal-prefix] Using synth-ai modal shim at {shim_candidate}; "
+                "pass --modal-cli /path/to/modal to override."
+            )
+        click.secho(warning, fg="yellow")
+        click.secho(
+            "[modal-prefix] modal_cli=modal selected=module-wrapper spec=yes",
+            fg="yellow",
+        )
+        return [sys.executable, "-m", "synth_ai.cli._modal_wrapper"]
+
+    if shim_candidate is not None:
+        raise click.ClickException(
+            "Modal CLI resolution found the synth-ai shim but the 'modal' package "
+            "is not importable in this environment. Install the official Modal CLI "
+            "or pass --modal-cli with its path."
+        )
+
+    raise click.ClickException(
+        "Modal CLI not found. Install the 'modal' package in this environment or pass "
+        "--modal-cli with an explicit path."
+    )
+
+
+def _build_modal_app_wrapper(original_script: Path) -> tuple[Path, Path]:
+    source_dir = original_script.parent.resolve()
+    repo_root = REPO_ROOT
+    temp_root = Path(tempfile.mkdtemp(prefix="synth_modal_app_"))
+
+    wrapper_source = textwrap.dedent(
+        f"""
+        from importlib import util as _util
+        from pathlib import Path as _Path
+        import sys as _sys
+
+        _source_dir = _Path({str(source_dir)!r}).resolve()
+        _module_path = _source_dir / {original_script.name!r}
+        _package_name = _source_dir.name
+        _repo_root = _Path({str(repo_root)!r}).resolve()
+        _synth_dir = _repo_root / "synth_ai"
+
+        for _path in (str(_source_dir), str(_source_dir.parent), str(_repo_root)):
+            if _path not in _sys.path:
+                _sys.path.insert(0, _path)
+
+        _spec = _util.spec_from_file_location("_synth_modal_target", str(_module_path))
+        if _spec is None or _spec.loader is None:
+            raise SystemExit("Unable to load modal task app from {original_script}")
+        _module = _util.module_from_spec(_spec)
+        _sys.modules.setdefault("_synth_modal_target", _module)
+        _spec.loader.exec_module(_module)
+
+        try:
+            from modal import App as _ModalApp
+            from modal import Image as _ModalImage
+        except Exception:
+            _ModalApp = None  # type: ignore[assignment]
+            _ModalImage = None  # type: ignore[assignment]
+
+        def _apply_local_mounts(image):
+            if _ModalImage is None or not isinstance(image, _ModalImage):
+                return image
+            mounts = [
+                (str(_source_dir), f"/root/{{_package_name}}"),
+                (str(_synth_dir), "/root/synth_ai"),
+            ]
+            for local_path, remote_path in mounts:
+                try:
+                    image = image.add_local_dir(local_path, remote_path=remote_path)
+                except Exception:
+                    pass
+            return image
+
+        if hasattr(_module, "image"):
+            _module.image = _apply_local_mounts(getattr(_module, "image"))
+
+        _candidate = getattr(_module, "app", None)
+        if _ModalApp is None or not isinstance(_candidate, _ModalApp):
+            candidate_modal_app = getattr(_module, "modal_app", None)
+            if _ModalApp is not None and isinstance(candidate_modal_app, _ModalApp):
+                _candidate = candidate_modal_app
+                setattr(_module, "app", _candidate)
+
+        if _ModalApp is not None and not isinstance(_candidate, _ModalApp):
+            raise SystemExit(
+                "Modal task app must expose an 'app = modal.App(...)' (or modal_app) attribute."
+            )
+
+        for remote_path in ("/root/synth_ai", f"/root/{{_package_name}}"):
+            if remote_path not in _sys.path:
+                _sys.path.insert(0, remote_path)
+
+        globals().update({{k: v for k, v in vars(_module).items() if not k.startswith("__")}})
+        app = getattr(_module, "app")
+        """
+    ).strip()
+
+    wrapper_path = temp_root / "__modal_wrapper__.py"
+    wrapper_path.write_text(wrapper_source + "\n", encoding="utf-8")
+    return wrapper_path, temp_root
+
 
 
 def _run_modal_script(
@@ -532,43 +1586,150 @@ def _run_modal_script(
     modal_name: str | None = None,
     dry_run: bool = False,
 ) -> None:
-    modal_path = shutil.which(modal_cli)
-    if modal_path is None:
-        raise click.ClickException(f"Modal CLI not found (looked for '{modal_cli}')")
-
     env_paths_list = [Path(p).resolve() for p in env_paths]
     path_strings = [str(p) for p in env_paths_list]
     _load_env_files_into_process(path_strings)
     _ensure_env_values(env_paths_list, script_path.parent)
     _load_env_values(env_paths_list)
+    # Ensure ENVIRONMENT_API_KEY is uploaded to backend for this org (matches registry path behavior)
+    try:
+        _preflight_env_key(env_paths_list, crash_on_failure=True)
+    except Exception as _pf_err:
+        raise click.ClickException(str(_pf_err)) from _pf_err
+
+    proc_env = os.environ.copy()
+    pythonpath_entries: list[str] = []
+    script_dir = script_path.parent.resolve()
+    pythonpath_entries.append(str(script_dir))
+    if (script_dir / "__init__.py").exists():
+        # Script lives inside a package; ensure the parent package directory is importable.
+        pythonpath_entries.append(str(script_dir.parent.resolve()))
+    pythonpath_entries.append(str(REPO_ROOT))
+    existing_pp = proc_env.get("PYTHONPATH")
+    if existing_pp:
+        pythonpath_entries.append(existing_pp)
+    unique_paths = list(dict.fromkeys(pythonpath_entries))
+    proc_env["PYTHONPATH"] = os.pathsep.join(unique_paths)
+
+    wrapper_info: tuple[Path, Path] | None = None
+    target_script = script_path
+    if command in {"serve", "deploy"}:
+        wrapper_path, temp_root = _build_modal_app_wrapper(script_path)
+        wrapper_info = (wrapper_path, temp_root)
+        target_script = wrapper_path
+
+        # Ensure the wrapper has access to the Synth AI source for intra-repo imports
+        if "PYTHONPATH" in proc_env:
+            proc_env["PYTHONPATH"] = os.pathsep.join(
+                [str(REPO_ROOT)] + proc_env["PYTHONPATH"].split(os.pathsep)
+            )
+        else:
+            proc_env["PYTHONPATH"] = str(REPO_ROOT)
 
-    cmd = [modal_path, command, str(script_path)]
-    if modal_name:
+    cmd = [*_modal_command_prefix(modal_cli), command, str(target_script)]
+    if modal_name and command == "deploy":
         cmd.extend(["--name", modal_name])
     if dry_run:
-        click.echo("Dry run: " + " ".join(cmd))
+        click.echo(
+            "Dry run: " + " ".join(shlex.quote(component) for component in cmd),
+            err=False,
+        )
         return
+    click.secho(
+        "[modal-exec] " + " ".join(shlex.quote(component) for component in cmd),
+        fg="cyan",
+    )
     try:
-        subprocess.run(cmd, check=True)
+        # Stream output live for better diagnostics
+        proc = subprocess.Popen(
+            cmd,
+            stdout=subprocess.PIPE,
+            stderr=subprocess.STDOUT,
+            text=True,
+            bufsize=1,
+            env=proc_env,
+        )
+        task_app_url = None
+        assert proc.stdout is not None
+        for line in proc.stdout:
+            click.echo(line, nl=False)
+            if task_app_url is None and ("modal.run" in line and "=>" in line):
+                parts = line.split("=>")
+                if len(parts) >= 2:
+                    task_app_url = parts[-1].strip()
+                    if task_app_url and env_paths_list:
+                        env_file = env_paths_list[0]
+                        _save_to_env_file(env_file, "TASK_APP_BASE_URL", task_app_url)
+                        click.echo(f"\n✓ Task app URL: {task_app_url}\n")
+        rc = proc.wait()
+        if rc != 0:
+            raise subprocess.CalledProcessError(rc, cmd)
     except subprocess.CalledProcessError as exc:
-        raise click.ClickException(f"modal {command} failed with exit code {exc.returncode}") from exc
+        raise click.ClickException(
+            f"modal {command} failed with exit code {exc.returncode}"
+        ) from exc
+    finally:
+        if wrapper_info is not None:
+            wrapper_path, temp_root = wrapper_info
+            with contextlib.suppress(Exception):
+                wrapper_path.unlink(missing_ok=True)
+            shutil.rmtree(temp_root, ignore_errors=True)
 
 
-def _preflight_env_key() -> None:
+def _preflight_env_key(env_paths: Sequence[Path] | None = None, *, crash_on_failure: bool = False) -> None:
     try:
-        raw_backend = os.environ.get("BACKEND_BASE_URL") or os.environ.get("SYNTH_BASE_URL") or "http://localhost:8000/api"
-        backend_base = raw_backend.rstrip('/')
-        if not backend_base.endswith('/api'):
-            backend_base = backend_base + '/api'
+        raw_backend = (
+            os.environ.get("BACKEND_BASE_URL")
+            or os.environ.get("SYNTH_BASE_URL")
+            or f"{PROD_BASE_URL_DEFAULT}/api"
+        )
+        backend_base = raw_backend.rstrip("/")
+        if not backend_base.endswith("/api"):
+            backend_base = backend_base + "/api"
         synth_key = os.environ.get("SYNTH_API_KEY") or ""
         env_api_key = (
-            os.environ.get("ENVIRONMENT_API_KEY")
-            or os.environ.get("dev_environment_api_key")
-            or os.environ.get("DEV_ENVIRONMENT_API_KEY")
-            or ""
-        )
+            os.environ.get("ENVIRONMENT_API_KEY") or os.environ.get("DEV_ENVIRONMENT_API_KEY") or ""
+        ).strip()
+
+        def _preview(value: str) -> str:
+            if len(value) <= 10:
+                return value
+            return f"{value[:6]}...{value[-4:]}"
+
+        minted = False
+        if not env_api_key:
+            secrets_module = _maybe_import("synth_ai.learning.rl.secrets")
+            try:
+                if secrets_module is None:
+                    raise RuntimeError("secrets module unavailable")
+                mint_env_key = secrets_module.mint_environment_api_key
+                env_api_key = mint_env_key()
+                os.environ["ENVIRONMENT_API_KEY"] = env_api_key
+                os.environ.setdefault("DEV_ENVIRONMENT_API_KEY", env_api_key)
+                minted = True
+                click.echo(
+                    f"[preflight] minted ENVIRONMENT_API_KEY ({_preview(env_api_key)})"
+                )
+            except Exception as mint_err:
+                if crash_on_failure:
+                    raise click.ClickException(
+                        f"[CRITICAL] Failed to mint ENVIRONMENT_API_KEY: {mint_err}"
+                    ) from mint_err
+                click.echo(
+                    f"[WARN] Failed to mint ENVIRONMENT_API_KEY automatically ({mint_err}); proceeding without upload"
+                )
+
+        if env_api_key and not os.environ.get("ENVIRONMENT_API_KEY"):
+            os.environ["ENVIRONMENT_API_KEY"] = env_api_key
+        if env_api_key and not os.environ.get("DEV_ENVIRONMENT_API_KEY"):
+            os.environ["DEV_ENVIRONMENT_API_KEY"] = env_api_key
+
+        if minted:
+            _persist_env_api_key(env_api_key, env_paths)
+
         if synth_key and env_api_key:
             import base64
+
             import httpx
 
             click.echo(f"[preflight] backend={backend_base}")
@@ -580,71 +1741,216 @@ def _preflight_env_key() -> None:
                 try:
                     from nacl.public import PublicKey, SealedBox
 
-                    pub = PublicKey(base64.b64decode(pk, validate=True))
+                    # Decode public key and build sealed box
+                    pk_bytes = base64.b64decode(pk, validate=True)
+                    pub = PublicKey(pk_bytes)
                     sb = SealedBox(pub)
-                    ct_b64 = base64.b64encode(sb.encrypt(env_api_key.encode('utf-8'))).decode()
+
+                    # Encrypt plaintext key
+                    ct_b64 = base64.b64encode(sb.encrypt(env_api_key.encode("utf-8"))).decode()
                     payload = {"name": "ENVIRONMENT_API_KEY", "ciphertext_b64": ct_b64}
-                    with httpx.Client(timeout=15.0, headers={"Authorization": f"Bearer {synth_key}", "Content-Type": "application/json"}) as c:
+
+                    # Emit diagnostic logging (safe previews + hashes only)
+                    try:
+                        import hashlib as _hash
+
+                        # Backend URL context
+                        click.echo(f"[preflight] posting to {backend_base.rstrip('/')}/v1/env-keys")
+
+                        # Public key diagnostics
+                        pk_sha256 = _hash.sha256(pk_bytes).hexdigest()
+                        click.echo(
+                            f"[preflight] public_key: b64_len={len(pk)} sha256={pk_sha256} head={pk[:16]} tail={pk[-16:]}"
+                        )
+
+                        # Plaintext diagnostics (never print full secret)
+                        _plain = env_api_key
+                        _plen = len(_plain)
+                        _ppref = (_plain[:6] + "…") if _plen > 10 else _plain
+                        _psuf = ("…" + _plain[-4:]) if _plen > 10 else ""
+                        _has_ws = any(ch.isspace() for ch in _plain)
+                        click.echo(
+                            f"[preflight] plaintext: len={_plen} preview={_ppref}{_psuf} has_ws={bool(_has_ws)}"
+                        )
+
+                        # Ciphertext diagnostics
+                        try:
+                            _ct_bytes = base64.b64decode(ct_b64, validate=True)
+                            _ct_sha256 = _hash.sha256(_ct_bytes).hexdigest()
+                            click.echo(
+                                f"[preflight] ciphertext: b64_len={len(ct_b64)} sha256={_ct_sha256} head={ct_b64[:16]} tail={ct_b64[-16:]}"
+                            )
+                        except Exception:
+                            click.echo("[preflight] ciphertext: invalid base64 (unexpected)")
+                    except Exception:
+                        # Best-effort logging only
+                        pass
+                    with httpx.Client(
+                        timeout=15.0,
+                        headers={
+                            "Authorization": f"Bearer {synth_key}",
+                            "Content-Type": "application/json",
+                        },
+                    ) as c:
                         click.echo("[preflight] upserting env key…")
                         up = c.post(f"{backend_base.rstrip('/')}/v1/env-keys", json=payload)
-                        click.echo(f"[preflight] upsert status={up.status_code}")
-                        click.echo("[preflight] verifying env key presence…")
-                        ver = c.get(f"{backend_base.rstrip('/')}/v1/env-keys/verify")
-                        if ver.status_code == 200 and (ver.json() or {}).get("present"):
-                            click.echo("✅ ENVIRONMENT_API_KEY upserted and verified in backend")
+                        body_snip = ""
+                        try:
+                            body_snip = up.text[:400] if up.text else ""
+                        except Exception:
+                            body_snip = ""
+                        click.echo(f"[preflight] upsert status={up.status_code}{(' body='+body_snip) if body_snip else ''}")
+
+                        # If upload succeeded (2xx), consider it successful even if verification fails
+                        # This handles cases where verification endpoint has issues
+                        if 200 <= up.status_code < 300:
+                            key_preview = (
+                                _preview(env_api_key)
+                            )
+                            click.echo(
+                                f"✅ ENVIRONMENT_API_KEY uploaded successfully ({key_preview})"
+                            )
+
+                            # Try verification, but don't fail if it doesn't work
+                            click.echo("[preflight] verifying env key presence…")
+                            try:
+                                ver = c.get(f"{backend_base.rstrip('/')}/v1/env-keys/verify")
+                                if ver.status_code == 200 and (ver.json() or {}).get("present"):
+                                    click.echo("✅ Key verified in backend")
+                                else:
+                                    click.echo(
+                                        f"⚠️  Verification returned {ver.status_code}, but upload succeeded - proceeding"
+                                    )
+                            except Exception as verify_err:
+                                click.echo(
+                                    f"⚠️  Verification check failed ({verify_err}), but upload succeeded - proceeding"
+                                )
                         else:
-                            click.echo("[WARN] ENVIRONMENT_API_KEY verification failed; proceeding anyway")
-                except Exception:
-                    click.echo("[WARN] Failed to encrypt/upload ENVIRONMENT_API_KEY; proceeding anyway")
-    except Exception:
-        click.echo("[WARN] Backend preflight for ENVIRONMENT_API_KEY failed; proceeding anyway")
+                            error_msg = (
+                                f"ENVIRONMENT_API_KEY upload failed with status {up.status_code}"
+                                + (f" body={body_snip}" if body_snip else "")
+                            )
+                            if crash_on_failure:
+                                raise click.ClickException(f"[CRITICAL] {error_msg}")
+                            click.echo(f"[WARN] {error_msg}; proceeding anyway")
+                except Exception as e:
+                    error_msg = f"Failed to encrypt/upload ENVIRONMENT_API_KEY: {e}"
+                    if crash_on_failure:
+                        raise click.ClickException(f"[CRITICAL] {error_msg}") from e
+                    click.echo(f"[WARN] {error_msg}; proceeding anyway")
+    except Exception as e:
+        error_msg = f"Backend preflight for ENVIRONMENT_API_KEY failed: {e}"
+        if crash_on_failure:
+            raise click.ClickException(f"[CRITICAL] {error_msg}") from e
+        click.echo(f"[WARN] {error_msg}; proceeding anyway")
 
 
 def _run_modal_with_entry(
-    entry: TaskAppEntry,
-    modal_cfg: ModalDeploymentConfig,
+    entry: TaskAppEntryType,
+    modal_cfg: ModalDeploymentConfigType,
     modal_cli: str,
     modal_name: str | None,
     env_paths: list[Path],
     command: str,
     *,
     dry_run: bool = False,
+    original_path: Path | None = None,
 ) -> None:
-    modal_path = shutil.which(modal_cli)
-    if modal_path is None:
-        raise click.ClickException(f"Modal CLI not found (looked for '{modal_cli}')")
-
     env_paths_list = [Path(p).resolve() for p in env_paths]
     dotenv_paths = [str(p) for p in env_paths_list]
     _load_env_files_into_process(dotenv_paths)
     fallback_dir = env_paths_list[0].parent if env_paths_list else Path.cwd()
     _ensure_env_values(env_paths_list, fallback_dir)
     _load_env_values(env_paths_list)
-    _preflight_env_key()
+    _preflight_env_key(env_paths_list, crash_on_failure=True)
+
+    inline_secret_values: dict[str, str] = {}
+    env_key = os.environ.get("ENVIRONMENT_API_KEY", "").strip()
+    if env_key:
+        inline_secret_values["ENVIRONMENT_API_KEY"] = env_key
+        inline_secret_values.setdefault("DEV_ENVIRONMENT_API_KEY", env_key)
+    aliases = os.environ.get("ENVIRONMENT_API_KEY_ALIASES", "").strip()
+    if aliases:
+        inline_secret_values["ENVIRONMENT_API_KEY_ALIASES"] = aliases
+    for vendor_key in ("GROQ_API_KEY", "OPENAI_API_KEY"):
+        val = os.environ.get(vendor_key, "").strip()
+        if val:
+            inline_secret_values[vendor_key] = val
+
+    if inline_secret_values:
+        preview = inline_secret_values.get("ENVIRONMENT_API_KEY", "")
+        shown = f"{preview[:6]}...{preview[-4:]}" if preview and len(preview) > 10 else preview
+        click.echo(f"[deploy] inline ENVIRONMENT_API_KEY prepared ({shown})")
+    else:
+        click.echo("[deploy] no inline ENVIRONMENT_API_KEY found; relying on Modal secrets/dotenv")
 
     script_path = _write_modal_entrypoint(
         entry,
         modal_cfg,
         modal_name,
         dotenv_paths=dotenv_paths,
+        original_path=original_path,
+        inline_secret_values=inline_secret_values,
     )
-    cmd = [modal_path, command, str(script_path)]
+    cmd = [*_modal_command_prefix(modal_cli), command, str(script_path)]
+    if modal_name and command == "deploy":
+        cmd.extend(["--name", modal_name])
+
+    proc_env = os.environ.copy()
+    pythonpath_entries: list[str] = [str(REPO_ROOT)]
+    if original_path is not None:
+        source_dir = Path(original_path).resolve().parent
+        pythonpath_entries.insert(0, str(source_dir))
+    existing_pp = proc_env.get("PYTHONPATH")
+    if existing_pp:
+        pythonpath_entries.append(existing_pp)
+    proc_env["PYTHONPATH"] = os.pathsep.join(list(dict.fromkeys(pythonpath_entries)))
 
     if dry_run:
-        click.echo("Dry run: " + " ".join(cmd))
+        click.echo("Dry run: " + " ".join(shlex.quote(component) for component in cmd))
         script_path.unlink(missing_ok=True)
         return
+    click.secho(
+        "[modal-exec] " + " ".join(shlex.quote(component) for component in cmd),
+        fg="cyan",
+    )
 
     try:
-        subprocess.run(cmd, check=True)
+        # Stream output live for better diagnostics
+        proc = subprocess.Popen(
+            cmd,
+            stdout=subprocess.PIPE,
+            stderr=subprocess.STDOUT,
+            text=True,
+            bufsize=1,
+            env=proc_env,
+        )
+        task_app_url = None
+        assert proc.stdout is not None
+        for line in proc.stdout:
+            # Echo lines as they arrive
+            click.echo(line, nl=False)
+            # Look for lines containing modal.run URLs
+            if task_app_url is None and ("modal.run" in line and "=>" in line):
+                parts = line.split("=>")
+                if len(parts) >= 2:
+                    task_app_url = parts[-1].strip()
+                    # Save URL immediately for convenience
+                    if task_app_url and env_paths_list:
+                        env_file = env_paths_list[0]
+                        _save_to_env_file(env_file, "TASK_APP_BASE_URL", task_app_url)
+                        click.echo(f"\n✓ Task app URL: {task_app_url}\n")
+        rc = proc.wait()
+        if rc != 0:
+            raise subprocess.CalledProcessError(rc, cmd)
     except subprocess.CalledProcessError as exc:
-        raise click.ClickException(f"modal {command} failed with exit code {exc.returncode}") from exc
+        raise click.ClickException(
+            f"modal {command} failed with exit code {exc.returncode}"
+        ) from exc
     finally:
         script_path.unlink(missing_ok=True)
 
 
-
-
 def _load_env_values(paths: list[Path], *, allow_empty: bool = False) -> dict[str, str]:
     values: dict[str, str] = {}
     for p in paths:
@@ -653,15 +1959,17 @@ def _load_env_values(paths: list[Path], *, allow_empty: bool = False) -> dict[st
         except FileNotFoundError:
             continue
         for line in content.splitlines():
-            if not line or line.lstrip().startswith('#') or '=' not in line:
+            if not line or line.lstrip().startswith("#") or "=" not in line:
                 continue
-            key, value = line.split('=', 1)
+            key, value = line.split("=", 1)
             if key and key not in values:
                 values[key.strip()] = value.strip()
     if not allow_empty and not values:
         raise click.ClickException("No environment values found")
     os.environ.update({k: v for k, v in values.items() if k and v})
     return values
+
+
 def _interactive_create_env(target_dir: Path) -> Path | None:
     env_path = (target_dir / ".env").resolve()
     if env_path.exists():
@@ -680,9 +1988,9 @@ def _parse_env_file(path: Path) -> dict[str, str]:
     data: dict[str, str] = {}
     try:
         for line in path.read_text(encoding="utf-8").splitlines():
-            if not line or line.lstrip().startswith('#') or '=' not in line:
+            if not line or line.lstrip().startswith("#") or "=" not in line:
                 continue
-            key, value = line.split('=', 1)
+            key, value = line.split("=", 1)
             data[key.strip()] = value.strip()
     except FileNotFoundError:
         pass
@@ -690,13 +1998,19 @@ def _parse_env_file(path: Path) -> dict[str, str]:
 
 
 def _interactive_fill_env(env_path: Path) -> Path | None:
+    if not sys.stdin.isatty():
+        raise click.ClickException(
+            "ENVIRONMENT_API_KEY missing. Provide --env-file or run `synth-ai setup` in an interactive shell to create one."
+        )
     existing = _parse_env_file(env_path) if env_path.exists() else {}
 
     def _prompt(label: str, *, default: str = "", required: bool) -> str | None:
         while True:
             try:
-                value = click.prompt(label, default=default, show_default=bool(default) or not required).strip()
-            except (click.exceptions.Abort, EOFError, KeyboardInterrupt):
+                value = click.prompt(
+                    label, default=default, show_default=bool(default) or not required
+                ).strip()
+            except (Abort, EOFError, KeyboardInterrupt):
                 click.echo("Aborted env creation.")
                 return None
             if value or not required:
@@ -727,6 +2041,10 @@ def _ensure_env_values(env_paths: list[Path], fallback_dir: Path) -> None:
     if (os.environ.get("ENVIRONMENT_API_KEY") or "").strip():
         return
     target = env_paths[0] if env_paths else (fallback_dir / ".env").resolve()
+    click.echo(
+        "⚠️  ENVIRONMENT_API_KEY not set. Run `uvx synth-ai setup`, "
+        "or pass --env-file pointing at a .env with ENVIRONMENT_API_KEY."
+    )
     result = _interactive_fill_env(target)
     if result is None:
         raise click.ClickException("ENVIRONMENT_API_KEY required to continue")
@@ -737,44 +2055,65 @@ def _ensure_env_values(env_paths: list[Path], fallback_dir: Path) -> None:
 
 
 def _deploy_entry(
-    entry: TaskAppEntry,
+    entry: TaskAppEntryType,
     modal_name: str | None,
     dry_run: bool,
     modal_cli: str,
     env_file: Sequence[str],
+    original_path: Path | None = None,
 ) -> None:
     modal_cfg = entry.modal
     if modal_cfg is None:
-        raise click.ClickException(f"Task app '{entry.app_id}' does not define Modal deployment settings")
+        raise click.ClickException(
+            f"Task app '{entry.app_id}' does not define Modal deployment settings"
+        )
 
-    env_paths = _determine_env_files(entry, env_file)
-    click.echo('Using env file(s): ' + ', '.join(str(p) for p in env_paths))
-    _run_modal_with_entry(entry, modal_cfg, modal_cli, modal_name, env_paths, command="deploy", dry_run=dry_run)
+    env_paths = _determine_env_files(entry, env_file, original_path=original_path)
+    click.echo("Using env file(s): " + ", ".join(str(p.resolve()) for p in env_paths))
+    _run_modal_with_entry(
+        entry,
+        modal_cfg,
+        modal_cli,
+        modal_name,
+        env_paths,
+        command="deploy",
+        dry_run=dry_run,
+        original_path=original_path,
+    )
 
 
 def _modal_serve_entry(
-    entry: TaskAppEntry,
+    entry: TaskAppEntryType,
     modal_name: str | None,
     modal_cli: str,
     env_file: Sequence[str],
+    original_path: Path | None = None,
 ) -> None:
     modal_cfg = entry.modal
     if modal_cfg is None:
-        raise click.ClickException(f"Task app '{entry.app_id}' does not define Modal deployment settings")
+        raise click.ClickException(
+            f"Task app '{entry.app_id}' does not define Modal deployment settings"
+        )
+
+    env_paths = _determine_env_files(entry, env_file, original_path=original_path)
+    click.echo("Using env file(s): " + ", ".join(str(p.resolve()) for p in env_paths))
+    _run_modal_with_entry(
+        entry,
+        modal_cfg,
+        modal_cli,
+        modal_name,
+        env_paths,
+        command="serve",
+        original_path=original_path,
+    )
 
-    env_paths = _determine_env_files(entry, env_file)
-    click.echo('Using env file(s): ' + ', '.join(str(p) for p in env_paths))
-    _run_modal_with_entry(entry, modal_cfg, modal_cli, modal_name, env_paths, command="serve")
 
-@click.group(
-    name='task-app',
-    help='Utilities for serving and deploying Synth task apps.'
-)
+@click.group(name="task-app", help="Utilities for serving and deploying Synth task apps.")
 def task_app_group() -> None:
     pass
 
 
-@task_app_group.command('list')
+@task_app_group.command("list")
 def list_apps() -> None:
     """List registered task apps."""
 
@@ -785,6 +2124,256 @@ def list_apps() -> None:
     for entry in entries:
         aliases = f" (aliases: {', '.join(entry.aliases)})" if entry.aliases else ""
         click.echo(f"- {entry.app_id}{aliases}: {entry.description}")
+
+
+@task_app_group.command("validate")
+@click.argument("app_id", type=str, required=True)
+@click.option(
+    "--url",
+    type=str,
+    default=None,
+    help="Task app URL to validate (if not provided, starts a local server)",
+)
+@click.option(
+    "--port",
+    type=int,
+    default=8765,
+    help="Port to use for temporary server (default: 8765)",
+)
+@click.option(
+    "--api-key",
+    type=str,
+    default=None,
+    envvar="ENVIRONMENT_API_KEY",
+    help="API key for authentication (default: $ENVIRONMENT_API_KEY)",
+)
+@click.option(
+    "--min-instances",
+    type=int,
+    default=10,
+    help="Minimum number of task instances required (default: 10)",
+)
+@click.option(
+    "--verbose",
+    "-v",
+    is_flag=True,
+    help="Show detailed information about the task app",
+)
+@click.option(
+    "--json",
+    "output_json",
+    is_flag=True,
+    help="Output results as JSON",
+)
+def validate_task_app_cmd(
+    app_id: str,
+    url: str | None,
+    port: int,
+    api_key: str | None,
+    min_instances: int,
+    verbose: bool,
+    output_json: bool,
+) -> None:
+    """Validate a task app deployment readiness.
+    
+    This command verifies that a task app is properly configured and ready to run
+    by checking all required HTTP endpoints, authentication, and task availability.
+    
+    By default, it starts a temporary local server for validation. You can also
+    validate a remote deployment by passing --url.
+    
+    \b
+    What gets validated:
+    • Root endpoint (/) responds correctly
+    • Health endpoint (/health) is accessible with proper authentication
+    • Info endpoint (/info) returns valid task metadata  
+    • Task info endpoint (/task_info) provides task instances
+    • Rollout endpoint (/rollout) is registered
+    • At least N task instances are available (default: 10)
+    
+    \b
+    Examples:
+    
+    \b
+    Validate grpo-crafter (starts local server automatically):
+        $ synth-ai task-app validate grpo-crafter
+    
+    \b
+    Validate sokoban with verbose output:
+        $ synth-ai task-app validate sokoban --verbose
+    
+    \b
+    Validate with custom port:
+        $ synth-ai task-app validate sokoban --port 9000
+    
+    \b
+    Validate a remote deployment:
+        $ synth-ai task-app validate grpo-crafter --url https://my-crafter.modal.run
+    
+    \b
+    Require at least 20 task instances:
+        $ synth-ai task-app validate grpo-crafter --min-instances 20
+    
+    \b
+    Get JSON output for automation:
+        $ synth-ai task-app validate sokoban --json
+    
+    \b
+    Common use cases:
+    • Pre-deployment verification: Check task app works before deploying to Modal
+    • CI/CD integration: Use --json flag for automated validation in pipelines
+    • Debug failing deployments: Use --verbose to see detailed endpoint responses
+    • Test API key configuration: Verify authentication is set up correctly
+    """
+    import socket
+    import subprocess
+    import tempfile
+    import time
+    
+    # Import the validate_task_app function defined in this module
+    from ._validate_task_app import validate_task_app  # type: ignore[attr-defined]
+    
+    proc = None
+    task_app_url = url
+    
+    try:
+        # If no URL provided, start a temporary server
+        if not task_app_url:
+            # Find an available port
+            def is_port_available(port: int) -> bool:
+                with socket.socket(socket.AF_INET, socket.SOCK_STREAM) as s:
+                    try:
+                        s.bind(("", port))
+                        return True
+                    except OSError:
+                        return False
+            
+            while not is_port_available(port):
+                port += 1
+            
+            task_app_url = f"http://localhost:{port}"
+            
+            if not output_json:
+                click.echo(f"Starting temporary {app_id} server on port {port}...")
+            
+            # Start the server in background
+            env = os.environ.copy()
+            if api_key:
+                env["ENVIRONMENT_API_KEY"] = api_key
+            
+            # Create a temporary trace DB and trace dir to avoid prompts
+            import tempfile
+            temp_dir = tempfile.mkdtemp()
+            temp_trace_db = os.path.join(temp_dir, "validate_trace.db")
+            temp_trace_dir = os.path.join(temp_dir, "traces")
+            os.makedirs(temp_trace_dir, exist_ok=True)
+            
+            proc = subprocess.Popen(
+                [
+                    "uv",
+                    "run",
+                    "synth-ai",
+                    "task-app",
+                    "serve",
+                    app_id,
+                    "--port",
+                    str(port),
+                    "--no-reload",
+                    "--trace",
+                    temp_trace_dir,
+                    "--trace-db",
+                    temp_trace_db,
+                ],
+                env=env,
+                stdin=subprocess.PIPE,  # Add stdin to handle any prompts
+                stdout=subprocess.DEVNULL if output_json else subprocess.PIPE,
+                stderr=subprocess.DEVNULL if output_json else subprocess.PIPE,
+                text=True,
+            )
+            
+            # Write empty input to stdin to skip any prompts
+            if proc.stdin:
+                try:
+                    proc.stdin.write("\n")
+                    proc.stdin.flush()
+                    proc.stdin.close()
+                except Exception:
+                    pass
+            
+            # Wait for server to be ready
+            if not output_json:
+                click.echo("Waiting for server to start...")
+            
+            import httpx
+            for _attempt in range(60):  # 30 seconds timeout
+                try:
+                    async def check_health():
+                        async with httpx.AsyncClient(timeout=2.0) as client:
+                            resp = await client.get(f"{task_app_url}/")
+                            return resp.status_code == 200
+                    
+                    if asyncio.run(check_health()):
+                        break
+                except Exception:
+                    pass
+                
+                # Check if process died
+                if proc.poll() is not None:
+                    stderr_output = ""
+                    if proc.stderr and not output_json:
+                        stderr_output = proc.stderr.read()
+                    click.echo(click.style("✗ Server process exited unexpectedly", fg="red"), err=True)
+                    if stderr_output and not output_json:
+                        click.echo(f"Error output:\n{stderr_output}", err=True)
+                    sys.exit(1)
+                
+                time.sleep(0.5)
+            else:
+                click.echo(click.style("✗ Server failed to start within 30 seconds", fg="red"), err=True)
+                sys.exit(1)
+            
+            if not output_json:
+                click.echo(click.style("✓ Server started", fg="green"))
+                click.echo()
+        
+        # Ensure URL doesn't have trailing slash
+        task_app_url = task_app_url.rstrip("/")
+        
+        async def _run() -> tuple[bool, dict[str, Any]]:
+            return await validate_task_app(
+                url=task_app_url,
+                api_key=api_key,
+                min_instances=min_instances,
+                verbose=verbose,
+            )
+        
+        success, results = asyncio.run(_run())
+        
+        if output_json:
+            import json as _json
+            click.echo(_json.dumps(results, indent=2))
+        
+        sys.exit(0 if success else 1)
+    
+    finally:
+        # Cleanup: stop the temporary server
+        if proc is not None:
+            if not output_json:
+                click.echo("\nStopping temporary server...")
+            try:
+                proc.terminate()
+                proc.wait(timeout=5)
+            except Exception:
+                proc.kill()
+        
+        # Cleanup temp trace DB
+        if not url and 'temp_dir' in locals():
+            import contextlib
+            import shutil
+            with contextlib.suppress(Exception):
+                shutil.rmtree(temp_dir, ignore_errors=True)
+
+
 def _load_env_files_into_process(paths: Sequence[str]) -> None:
     for p in paths:
         try:
@@ -792,9 +2381,9 @@ def _load_env_files_into_process(paths: Sequence[str]) -> None:
         except Exception:
             continue
         for line in txt.splitlines():
-            if not line or line.startswith('#') or '=' not in line:
+            if not line or line.startswith("#") or "=" not in line:
                 continue
-            k, v = line.split('=', 1)
+            k, v = line.split("=", 1)
             key = k.strip()
             val = v.strip().strip('"').strip("'")
             # Load into process, but allow overriding if the current value is empty
@@ -804,55 +2393,206 @@ def _load_env_files_into_process(paths: Sequence[str]) -> None:
                     os.environ[key] = val
 
 
-
-@click.command('serve')
-@click.argument('app_id', type=str, required=False)
-@click.option('--host', default='0.0.0.0', show_default=True)
-@click.option('--port', default=8001, show_default=True, type=int)
-@click.option('--env-file', multiple=True, type=click.Path(), help='Extra .env files to load')
-@click.option('--reload/--no-reload', 'reload_flag', default=False, help='Enable uvicorn auto-reload')
-@click.option('--force/--no-force', 'force', default=False, help='Kill any process already bound to the selected port before starting')
-@click.option('--trace', 'trace_dir', type=click.Path(), default=None, help='Enable tracing and write SFT JSONL files to this directory')
-@click.option('--trace-db', 'trace_db', type=click.Path(), default=None, help='Override local trace DB path (maps to SQLD_DB_PATH)')
+@click.command("serve")
+@click.argument("app_id", type=str, required=False)
+@click.option("--host", default="0.0.0.0", show_default=True)
+@click.option("--port", default=None, type=int, help="Port to serve on (default: 8001)")
+@click.option("--env-file", multiple=True, type=click.Path(), help="Extra .env files to load")
+@click.option(
+    "--reload/--no-reload", "reload_flag", default=False, help="Enable uvicorn auto-reload"
+)
+@click.option(
+    "--force/--no-force",
+    "force",
+    default=False,
+    help="Kill any process already bound to the selected port before starting",
+)
+@click.option(
+    "--trace",
+    "trace_dir",
+    type=click.Path(),
+    default=None,
+    help="Enable tracing and write SFT JSONL files to this directory (default: traces/v3)",
+)
+@click.option(
+    "--trace-db",
+    "trace_db",
+    type=click.Path(),
+    default=None,
+    help="Override local trace DB path (default: traces/v3/synth_ai.db)",
+)
 def serve_command(
     app_id: str | None,
     host: str,
-    port: int,
+    port: int | None,
     env_file: Sequence[str],
     reload_flag: bool,
     force: bool,
     trace_dir: str | None,
     trace_db: str | None,
 ) -> None:
-    choice = _select_app_choice(app_id, purpose="serve")
-    entry = choice.ensure_entry()
-    _serve_entry(entry, host, port, env_file, reload_flag, force, trace_dir=trace_dir, trace_db=trace_db)
-
-
-@task_app_group.command('serve')
-@click.argument('app_id', type=str, required=False)
-@click.option('--host', default='0.0.0.0', show_default=True)
-@click.option('--port', default=8001, show_default=True, type=int)
-@click.option('--env-file', multiple=True, type=click.Path(), help='Extra .env files to load')
-@click.option('--reload/--no-reload', 'reload_flag', default=False, help='Enable uvicorn auto-reload')
-@click.option('--force/--no-force', 'force', default=False, help='Kill any process already bound to the selected port before starting')
-@click.option('--trace', 'trace_dir', type=click.Path(), default=None, help='Enable tracing and write SFT JSONL files to this directory')
-@click.option('--trace-db', 'trace_db', type=click.Path(), default=None, help='Override local trace DB path (maps to SQLD_DB_PATH)')
+    return None
+
+
+@task_app_group.command("info")
+@click.option(
+    "--base",
+    "base_url",
+    default=None,
+    help="Task app base URL (default: TASK_APP_BASE_URL or http://127.0.0.1:8001)",
+)
+@click.option(
+    "--api-key",
+    default=None,
+    help="Environment API key (default: ENVIRONMENT_API_KEY or dev fallbacks)",
+)
+@click.option(
+    "--seed",
+    "seeds",
+    multiple=True,
+    type=int,
+    help="Optional seed(s) to request specific instances (repeatable)",
+)
+def info_command(base_url: str | None, api_key: str | None, seeds: tuple[int, ...]) -> None:
+    """Fetch Task App /task_info with authentication and print JSON."""
+    import json as _json
+    import os as _os
+
+    import requests as _requests
+
+    base = (base_url or _os.getenv("TASK_APP_BASE_URL") or "http://127.0.0.1:8001").rstrip("/")
+
+    # Resolve API key, permitting dev fallbacks
+    auth_module = _maybe_import("synth_ai.task.auth")
+    if auth_module is not None:
+        _norm_key = getattr(auth_module, "normalize_environment_api_key", lambda: _os.getenv("ENVIRONMENT_API_KEY"))
+    else:
+        _norm_key = lambda: _os.getenv("ENVIRONMENT_API_KEY")  # noqa: E731
+    key = (api_key or _norm_key() or "").strip()
+    if not key:
+        raise click.ClickException("Missing API key. Provide --api-key or set ENVIRONMENT_API_KEY.")
+
+    headers: dict[str, str] = {"X-API-Key": key, "Authorization": f"Bearer {key}"}
+    aliases = (_os.getenv("ENVIRONMENT_API_KEY_ALIASES") or "").strip()
+    keys_csv = (
+        ",".join([key] + [p.strip() for p in aliases.split(",") if p.strip()]) if aliases else key
+    )
+    if keys_csv:
+        headers["X-API-Keys"] = keys_csv
+
+    params: list[tuple[str, str]] = []
+    for s in seeds:
+        params.append(("seed", str(int(s))))
+
+    url = f"{base}/task_info"
+    try:
+        r = _requests.get(url, headers=headers, params=params or None, timeout=30)
+    except Exception as exc:
+        raise click.ClickException(f"Request failed: {exc}") from exc
+    if not (200 <= r.status_code < 300):
+        ct = r.headers.get("content-type", "")
+        detail = r.text
+        if ct.startswith("application/json"):
+            with contextlib.suppress(Exception):
+                detail = _json.dumps(r.json(), indent=2)
+        raise click.ClickException(f"{url} returned {r.status_code}:\n{detail}")
+
+    data = (
+        r.json()
+        if r.headers.get("content-type", "").startswith("application/json")
+        else {"raw": r.text}
+    )
+    click.echo(_json.dumps(data, indent=2, sort_keys=True))
+
+
+@task_app_group.command("serve")
+@click.argument("app_id", type=str, required=False)
+@click.option("--host", default="0.0.0.0", show_default=True)
+@click.option("--port", default=None, type=int, help="Port to serve on (default: 8001)")
+@click.option("--env-file", multiple=True, type=click.Path(), help="Extra .env files to load")
+@click.option(
+    "--reload/--no-reload", "reload_flag", default=False, help="Enable uvicorn auto-reload"
+)
+@click.option(
+    "--force/--no-force",
+    "force",
+    default=False,
+    help="Kill any process already bound to the selected port before starting",
+)
+@click.option(
+    "--trace",
+    "trace_dir",
+    type=click.Path(),
+    default=None,
+    help="Enable tracing and write SFT JSONL files to this directory (default: traces/v3)",
+)
+@click.option(
+    "--trace-db",
+    "trace_db",
+    type=click.Path(),
+    default=None,
+    help="Override local trace DB path (default: traces/v3/synth_ai.db)",
+)
 def serve_task_group(
     app_id: str | None,
     host: str,
-    port: int,
+    port: int | None,
     env_file: Sequence[str],
     reload_flag: bool,
     force: bool,
     trace_dir: str | None,
     trace_db: str | None,
 ) -> None:
+    """Serve a TaskAppConfig-based task app using uvicorn."""
+    import contextlib
+    
+    if not host:
+        host = "0.0.0.0"
+    
+    if port is None:
+        port = 8001
+    
+    # Auto-enable tracing by default
+    try:
+        auto_trace = os.getenv("SYNTH_AUTO_TRACE", "1")
+        auto_trace_enabled = auto_trace not in {"0", "false", "False", ""}
+    except Exception:
+        auto_trace_enabled = True
+
+    if auto_trace_enabled:
+        demo_base = Path(os.environ.get("SYNTH_DEMO_DIR") or Path.cwd())
+        if trace_dir is None:
+            default_trace_dir = (demo_base / "traces" / "v3").resolve()
+            with contextlib.suppress(Exception):
+                default_trace_dir.mkdir(parents=True, exist_ok=True)
+            trace_dir = str(default_trace_dir)
+            click.echo(f"[trace] Using trace directory: {trace_dir}")
+        if trace_dir and trace_db is None:
+            default_trace_db = (Path(trace_dir) / "synth_ai.db").resolve()
+            with contextlib.suppress(Exception):
+                default_trace_db.parent.mkdir(parents=True, exist_ok=True)
+            trace_db = str(default_trace_db)
+            click.echo(f"[trace] Using trace DB: {trace_db}")
+    
+    # Select and serve the app
     choice = _select_app_choice(app_id, purpose="serve")
     entry = choice.ensure_entry()
-    _serve_entry(entry, host, port, env_file, reload_flag, force, trace_dir=trace_dir, trace_db=trace_db)
+    _serve_entry(
+        entry,
+        host,
+        port,
+        env_file,
+        reload_flag,
+        force,
+        trace_dir=trace_dir,
+        trace_db=trace_db,
+    )
 
-def _determine_env_files(entry: TaskAppEntry, user_env_files: Sequence[str]) -> list[Path]:
+
+
+def _determine_env_files(
+    entry: TaskAppEntryType, user_env_files: Sequence[str], *, original_path: Path | None = None
+) -> list[Path]:
     resolved: list[Path] = []
     for candidate in user_env_files:
         p = Path(candidate).expanduser()
@@ -862,19 +2602,46 @@ def _determine_env_files(entry: TaskAppEntry, user_env_files: Sequence[str]) ->
     if resolved:
         return resolved
 
-    defaults = [Path(path).expanduser() for path in (entry.env_files or []) if Path(path).expanduser().exists()]
-    if defaults:
-        return defaults
-
-    env_candidates = sorted(REPO_ROOT.glob('**/*.env'))
-    if not env_candidates:
-        raise click.ClickException('No env file found. Pass --env-file explicitly.')
-
-    click.echo('Select env file to load:')
-    for idx, path in enumerate(env_candidates, start=1):
-        click.echo(f"  {idx}) {path}")
-    choice = click.prompt('Enter choice', type=click.IntRange(1, len(env_candidates)))
-    return [env_candidates[choice - 1]]
+    declared: list[Path] = []
+    for candidate in getattr(entry, "env_files", ()) or ():
+        try:
+            p = Path(candidate).expanduser()
+        except Exception:
+            continue
+        if p.exists() and p.is_file():
+            declared.append(p)
+    if declared:
+        return declared
+
+    def _append_candidate(collection: list[Path], candidate: Path) -> None:
+        if candidate.exists() and candidate.is_file() and candidate not in collection:
+            collection.append(candidate)
+
+    auto_candidates: list[Path] = []
+
+    search_dirs: list[Path] = []
+    if original_path is not None:
+        search_dirs.append(original_path.parent.resolve())
+        for parent in original_path.parent.resolve().parents:
+            search_dirs.append(parent)
+    cwd = Path.cwd().resolve()
+    if cwd not in search_dirs:
+        search_dirs.append(cwd)
+    repo_root = REPO_ROOT.resolve()
+    if repo_root not in search_dirs:
+        search_dirs.append(repo_root)
+
+    for directory in search_dirs:
+        _append_candidate(auto_candidates, directory / ".env")
+        for candidate in sorted(directory.glob("*.env")):
+            _append_candidate(auto_candidates, candidate)
+
+    if auto_candidates:
+        return [auto_candidates[0]]
+
+    raise click.ClickException(
+        "No .env file discovered automatically. Pass --env-file /path/to/.env or generate one with `uvx synth-ai setup`."
+    )
 
 
 def _ensure_port_free(port: int, host: str, *, force: bool) -> None:
@@ -889,7 +2656,9 @@ def _ensure_port_free(port: int, host: str, *, force: bool) -> None:
         return
 
     try:
-        out = subprocess.run(["lsof", "-ti", f"TCP:{port}"], capture_output=True, text=True, check=False)
+        out = subprocess.run(
+            ["lsof", "-ti", f"TCP:{port}"], capture_output=True, text=True, check=False
+        )
         pids = [pid for pid in out.stdout.strip().splitlines() if pid]
     except FileNotFoundError:
         pids = []
@@ -904,7 +2673,7 @@ def _ensure_port_free(port: int, host: str, *, force: bool) -> None:
         try:
             os.kill(int(pid), signal.SIGTERM)
         except Exception as exc:
-            raise click.ClickException(f'Failed to terminate PID {pid}: {exc}')
+            raise click.ClickException(f"Failed to terminate PID {pid}: {exc}") from exc
 
     time.sleep(0.5)
 
@@ -916,16 +2685,134 @@ def _ensure_port_free(port: int, host: str, *, force: bool) -> None:
             try:
                 os.kill(int(pid), signal.SIGKILL)
             except Exception as exc:
-                raise click.ClickException(f'Failed to force terminate PID {pid}: {exc}')
+                raise click.ClickException(f"Failed to force terminate PID {pid}: {exc}") from exc
         time.sleep(0.5)
 
     with socket.socket(socket.AF_INET, socket.SOCK_STREAM) as s:
         in_use_after = s.connect_ex((host, port)) == 0
     if in_use_after:
-        raise click.ClickException(f'Port {port} is still in use after attempting to terminate processes.')
+        raise click.ClickException(
+            f"Port {port} is still in use after attempting to terminate processes."
+        )
+
+
+def _save_to_env_file(env_path: Path, key: str, value: str) -> None:
+    """Save or update a key-value pair in the .env file."""
+    try:
+        # Read existing .env
+        existing_lines = []
+        if env_path.exists():
+            existing_lines = env_path.read_text().splitlines()
+        else:
+            env_path.parent.mkdir(parents=True, exist_ok=True)
+
+        # Check if key already exists and update it
+        key_updated = False
+        new_lines = []
+        for line in existing_lines:
+            if line.strip().startswith(f"{key}="):
+                new_lines.append(f"{key}={value}")
+                key_updated = True
+            else:
+                new_lines.append(line)
+
+        if key_updated:
+            # Write updated lines back
+            env_path.write_text("\n".join(new_lines) + "\n")
+            click.echo(f"Updated {key} in {env_path}")
+        else:
+            # Append to .env
+            with open(env_path, "a") as f:
+                if existing_lines and not existing_lines[-1].strip():
+                    # File exists and last line is not empty
+                    pass
+                elif existing_lines:
+                    # Add newline before appending
+                    f.write("\n")
+                f.write(f"{key}={value}\n")
+        click.echo(f"Saved {key} to {env_path}")
+    except Exception as e:
+        click.echo(f"Warning: Could not save {key} to .env: {e}", err=True)
+
+
+def _persist_env_api_key(env_api_key: str, env_paths: Sequence[Path] | None) -> None:
+    """Persist ENVIRONMENT_API_KEY to provided env files (or default .env)."""
+    targets: list[Path] = []
+    seen: set[Path] = set()
+    for path in env_paths or ():
+        try:
+            resolved = Path(path).resolve()
+        except Exception:
+            continue
+        if resolved in seen:
+            continue
+        seen.add(resolved)
+        targets.append(resolved)
+
+    if not targets:
+        demo_dir = Path(os.environ.get("SYNTH_DEMO_DIR") or Path.cwd())
+        targets.append((demo_dir / ".env").resolve())
+
+    for target in targets:
+        _save_to_env_file(target, "ENVIRONMENT_API_KEY", env_api_key)
+
+
+def _validate_required_env_keys() -> None:
+    """Validate required environment keys are set, prompting if missing."""
+    # Use demo directory .env file if set, otherwise current directory
+    demo_base = Path(os.environ.get("SYNTH_DEMO_DIR") or Path.cwd())
+    env_file = demo_base / ".env"
+
+    if env_file.exists():
+        try:
+            from dotenv import load_dotenv
+
+            load_dotenv(env_file, override=False)
+        except Exception:
+            pass  # Best effort
+
+    env_api_key = os.environ.get("ENVIRONMENT_API_KEY", "").strip()
+
+    if not env_api_key:
+        env_api_key = input("Please enter your RL Environment API key:\n> ").strip()
+        if not env_api_key:
+            raise click.ClickException("RL Environment API key is required to start the server")
+        os.environ["ENVIRONMENT_API_KEY"] = env_api_key
+        _save_to_env_file(env_file, "ENVIRONMENT_API_KEY", env_api_key)
+
+    # Check for Groq API key
+    groq_api_key = os.environ.get("GROQ_API_KEY", "").strip()
+
+    if not groq_api_key:
+        click.echo("\nInference API key configuration:")
+        click.echo("This workflow requires a Groq API key.")
+        groq_api_key = input("Groq API key (or press Enter to skip): ").strip()
+        if groq_api_key:
+            os.environ["GROQ_API_KEY"] = groq_api_key
+            _save_to_env_file(env_file, "GROQ_API_KEY", groq_api_key)
+
+
+def _print_demo_next_steps_if_applicable() -> None:
+    """Print next steps if currently in a demo directory."""
+    try:
+        cwd = Path.cwd().resolve()
+        demo_dir = _load_demo_directory()
+
+        if demo_dir and demo_dir == cwd and (cwd / "run_local_rollout_traced.py").exists():
+            click.echo("\n" + "=" * 60)
+            click.echo("Next step: Collect traced rollouts")
+            click.echo("=" * 60)
+            click.echo("\nIn another terminal, run:")
+            click.echo(f"  cd {cwd}")
+            click.echo("  uv run python run_local_rollout_traced.py")
+            click.echo("\nRun this 5-10 times to collect diverse traces.")
+            click.echo("=" * 60 + "\n")
+    except Exception:
+        pass
+
 
 def _serve_entry(
-    entry: TaskAppEntry,
+    entry: TaskAppEntryType,
     host: str,
     port: int,
     env_file: Sequence[str],
@@ -940,33 +2827,51 @@ def _serve_entry(
 
     trace_enabled = trace_dir is not None or trace_db is not None
     if trace_enabled:
-        os.environ['TASKAPP_TRACING_ENABLED'] = '1'
+        os.environ["TASKAPP_TRACING_ENABLED"] = "1"
+
+        # Ensure paths are absolute relative to demo directory
+        demo_base = Path(os.environ.get("SYNTH_DEMO_DIR") or Path.cwd())
+
         if trace_dir is not None:
             dir_path = Path(trace_dir).expanduser()
+            if not dir_path.is_absolute():
+                dir_path = (demo_base / dir_path).resolve()
             try:
                 dir_path.mkdir(parents=True, exist_ok=True)
             except Exception as exc:
-                raise click.ClickException(f"Failed to create trace directory {dir_path}: {exc}") from exc
-            os.environ['TASKAPP_SFT_OUTPUT_DIR'] = str(dir_path)
+                raise click.ClickException(
+                    f"Failed to create trace directory {dir_path}: {exc}"
+                ) from exc
+            os.environ["TASKAPP_SFT_OUTPUT_DIR"] = str(dir_path)
             click.echo(f"Tracing enabled. SFT JSONL will be written to {dir_path}")
         if trace_db is not None:
             db_path = Path(trace_db).expanduser()
-            os.environ['SQLD_DB_PATH'] = str(db_path)
-            os.environ.pop('TURSO_LOCAL_DB_URL', None)
+            if not db_path.is_absolute():
+                db_path = (demo_base / db_path).resolve()
+            # Construct the sqlite URL from the absolute path
+            db_url = f"sqlite+aiosqlite:///{db_path}"
+            os.environ["SQLD_DB_PATH"] = str(db_path)
+            os.environ["TURSO_LOCAL_DB_URL"] = db_url
             click.echo(f"Tracing DB path set to {db_path}")
-        from synth_ai.tracing_v3.config import CONFIG as TRACE_CONFIG
-        # recompute db_url based on current environment
-        new_db_url = os.getenv('TURSO_LOCAL_DB_URL') or TRACE_CONFIG.db_url
-        TRACE_CONFIG.db_url = new_db_url
-        if new_db_url:
-            os.environ['TURSO_LOCAL_DB_URL'] = new_db_url
-            click.echo(f"Tracing DB URL resolved to {new_db_url}")
-    elif os.getenv('TASKAPP_TRACING_ENABLED'):
+        tracing_config_module = _maybe_import("synth_ai.tracing_v3.config")
+        if tracing_config_module is not None:
+            trace_config = tracing_config_module.CONFIG
+            new_db_url = os.getenv("TURSO_LOCAL_DB_URL") or trace_config.db_url
+            trace_config.db_url = new_db_url
+            if new_db_url:
+                click.echo(f"Tracing DB URL resolved to {new_db_url}")
+    elif os.getenv("TASKAPP_TRACING_ENABLED"):
         click.echo("Tracing enabled via environment variables")
 
     _ensure_port_free(port, host, force=force)
 
-    _preflight_env_key()
+    _validate_required_env_keys()
+    env_path_objs = [Path(p) for p in env_files if p]
+    _preflight_env_key(env_path_objs)
+
+    # Print next steps if in demo context
+    if trace_enabled:
+        _print_demo_next_steps_if_applicable()
 
     run_task_app(
         entry.config_factory,
@@ -977,91 +2882,168 @@ def _serve_entry(
     )
 
 
-@task_app_group.command('deploy')
-@click.argument("app_id", type=str, required=False)
-@click.option("--name", "modal_name", default=None, help="Override Modal app name")
-@click.option("--dry-run", is_flag=True, help="Print modal deploy command without executing")
-@click.option("--modal-cli", default="modal", help="Path to modal CLI executable")
-@click.option('--env-file', multiple=True, type=click.Path(), help='Env file to load into the container (can be repeated)')
-def deploy_app(app_id: str | None, modal_name: str | None, dry_run: bool, modal_cli: str, env_file: Sequence[str]) -> None:
-    """Deploy a task app to Modal."""
-
-    choice = _select_app_choice(app_id, purpose="deploy")
-
-    if choice.modal_script:
-        env_paths = _resolve_env_paths_for_script(choice.modal_script, env_file)
-        click.echo('Using env file(s): ' + ', '.join(str(p) for p in env_paths))
-        _run_modal_script(choice.modal_script, modal_cli, "deploy", env_paths, modal_name=modal_name, dry_run=dry_run)
-        return
-
-    entry = choice.ensure_entry()
-    _deploy_entry(entry, modal_name, dry_run, modal_cli, env_file)
-
-@task_app_group.command('modal-serve')
-@click.argument('app_id', type=str, required=False)
-@click.option('--modal-cli', default='modal', help='Path to modal CLI executable')
-@click.option('--name', 'modal_name', default=None, help='Override Modal app name (optional)')
-@click.option('--env-file', multiple=True, type=click.Path(), help='Env file to load into the container (can be repeated)')
-def modal_serve_app(app_id: str | None, modal_cli: str, modal_name: str | None, env_file: Sequence[str]) -> None:
-    choice = _select_app_choice(app_id, purpose="modal-serve")
-
-    if choice.modal_script:
-        env_paths = _resolve_env_paths_for_script(choice.modal_script, env_file)
-        click.echo('Using env file(s): ' + ', '.join(str(p) for p in env_paths))
-        _run_modal_script(choice.modal_script, modal_cli, "serve", env_paths, modal_name=modal_name)
-        return
-
-    entry = choice.ensure_entry()
-    _modal_serve_entry(entry, modal_name, modal_cli, env_file)
-
-
 def _write_modal_entrypoint(
-    entry: TaskAppEntry,
-    modal_cfg: ModalDeploymentConfig,
+    entry: TaskAppEntryType,
+    modal_cfg: ModalDeploymentConfigType,
     override_name: str | None,
     *,
     dotenv_paths: Sequence[str] | None = None,
+    original_path: Path | None = None,
+    inline_secret_values: dict[str, str] | None = None,
 ) -> Path:
     modal_name = override_name or modal_cfg.app_name
 
+    # For dynamically discovered apps, import the module by its package path
+    # Compute the module name relative to the mounted repo root (/opt/synth_ai_repo)
+    remote_file_str: str | None = None
+    if original_path:
+        try:
+            # Build lookup of local->remote mounts
+            mount_map: list[tuple[Path, Path]] = [
+                (Path(local).resolve(), Path(remote))
+                for (local, remote) in modal_cfg.extra_local_dirs
+            ]
+            orig = Path(original_path).resolve()
+            for local_src, remote_dst in mount_map:
+                with contextlib.suppress(Exception):
+                    if orig.is_relative_to(local_src):  # py311+
+                        remote_file_str = str((remote_dst / orig.relative_to(local_src)).resolve())
+                        break
+                try:
+                    rel = orig.relative_to(local_src)
+                    remote_file_str = str((remote_dst / rel).resolve())
+                    break
+                except Exception:
+                    pass
+        except Exception:
+            remote_file_str = None
     module_name = entry.config_factory.__module__
+
+    # Prefer a guaranteed mount for the discovered file to avoid package import issues
+    guaranteed_file_str: str | None = None
+    if original_path:
+        guaranteed_file_str = str(
+            (Path("/opt/synth_ai_repo/__local_task_app__") / Path(original_path).stem).with_suffix(
+                ".py"
+            )
+        )
+
     dotenv_paths = [str(Path(path)) for path in (dotenv_paths or [])]
 
     pip_packages = list(modal_cfg.pip_packages)
-
+    # Ensure synth-ai (matching host version if available) is installed in the container
+    synth_pkg = "synth-ai"
+    host_synth = _maybe_import("synth_ai")
+    if host_synth is not None:
+        host_ver = getattr(host_synth, "__version__", None)
+        if host_ver:
+            synth_pkg = f"synth-ai=={host_ver}"
+    if not any(str(p).startswith("synth-ai") for p in pip_packages):
+        pip_packages.insert(0, synth_pkg)
+
+    apt_packages = list(modal_cfg.apt_packages)
+    click.echo(f"[DEBUG] modal_cfg.apt_packages type: {type(modal_cfg.apt_packages)}")
+    click.echo(f"[DEBUG] modal_cfg.apt_packages value: {modal_cfg.apt_packages}")
+    click.echo(f"[DEBUG] apt_packages after list(): {apt_packages}")
+    
     local_dirs = [(str(Path(src)), dst) for src, dst in modal_cfg.extra_local_dirs]
+    # Also mount the host synth_ai source if available to ensure latest code is used
+    if host_synth is not None:
+        try:
+            host_synth_dir = Path(host_synth.__file__).resolve().parent
+            sy_dst = "/opt/synth_ai_repo/synth_ai"
+            candidate = (str(host_synth_dir), sy_dst)
+            if candidate not in local_dirs:
+                local_dirs.insert(0, candidate)
+        except Exception:
+            pass
+    # Ensure the discovered app directory is mounted, regardless of modal_cfg
+    if original_path:
+        discovered_dir = str(Path(original_path).resolve().parent)
+        mount_dst = "/opt/synth_ai_repo/__local_task_app__"
+        if (discovered_dir, mount_dst) not in local_dirs:
+            local_dirs.append((discovered_dir, mount_dst))
     secret_names = list(modal_cfg.secret_names)
     volume_mounts = [(name, mount) for name, mount in modal_cfg.volume_mounts]
+    inline_secret_values = {k: v for k, v in (inline_secret_values or {}).items() if v}
 
     script = f"""from __future__ import annotations
 
 import importlib
+import importlib.util
 import sys
+import os
+import shutil
+import tempfile
+from pathlib import Path as _Path
+import fnmatch
 sys.path.insert(0, '/opt/synth_ai_repo')
 
 from modal import App, Image, Secret, Volume, asgi_app
 
-from synth_ai.task.apps import registry
-from synth_ai.task.server import create_task_app
+ # Defer importing synth_ai until inside fastapi_app to avoid local import errors
 
 ENTRY_ID = {entry.app_id!r}
 MODAL_APP_NAME = {modal_name!r}
 MODULE_NAME = {module_name!r}
+MODULE_FILE = {guaranteed_file_str or remote_file_str!r}
 DOTENV_PATHS = {dotenv_paths!r}
+INLINE_SECRET_VALUES = {inline_secret_values!r}
 
 image = Image.debian_slim(python_version={modal_cfg.python_version!r})
 
+# CRITICAL: Install iverilog for Verilog task app (hardcoded to prevent config issues)
+if {entry.app_id!r} == "grpo-verilog":
+    image = image.apt_install("iverilog")
+
+# Install apt packages first (before pip)
+apt_packages = {apt_packages!r}
+if apt_packages:
+    image = image.apt_install(*apt_packages)
+
 pip_packages = {pip_packages!r}
 if pip_packages:
     image = image.pip_install(*pip_packages)
 
 local_dirs = {local_dirs!r}
+
+def _copy_tree_filtered(src_dir: str) -> str:
+    src = _Path(src_dir)
+    temp_dir = _Path(tempfile.mkdtemp(prefix='synth_mount_'))
+
+    exclude_dirs = {".cache", ".git", "__pycache__"}
+    exclude_globs = ['*.db', '*.db-journal', '*-wal', '*-shm']
+
+    for root, dirs, files in os.walk(src):
+        rel_root = _Path(root).relative_to(src)
+        # filter dirs in-place
+        dirs[:] = [d for d in dirs if d not in exclude_dirs]
+        # ensure target directory exists
+        target_dir = (temp_dir / rel_root)
+        target_dir.mkdir(parents=True, exist_ok=True)
+        # copy files with filtering
+        for name in files:
+            if any(fnmatch.fnmatch(name, pat) for pat in exclude_globs):
+                continue
+            src_file = _Path(root) / name
+            dst_file = target_dir / name
+            try:
+                shutil.copy2(src_file, dst_file)
+            except Exception:
+                # ignore problematic files
+                continue
+    return str(temp_dir)
+
 for local_src, remote_dst in local_dirs:
-    image = image.add_local_dir(local_src, remote_dst)
+    safe_src = _copy_tree_filtered(local_src)
+    image = image.add_local_dir(safe_src, remote_dst)
 
 secrets = {secret_names!r}
 secret_objs = [Secret.from_name(name) for name in secrets]
 
+if INLINE_SECRET_VALUES:
+    secret_objs.append(Secret.from_dict(INLINE_SECRET_VALUES))
+
 if DOTENV_PATHS:
     secret_objs.extend(Secret.from_dotenv(path) for path in DOTENV_PATHS)
 
@@ -1070,13 +3052,6 @@ volume_map = {{}}
 for vol_name, mount_path in volume_mounts:
     volume_map[mount_path] = Volume.from_name(vol_name, create_if_missing=True)
 
-importlib.import_module(MODULE_NAME)
-
-entry = registry.get(ENTRY_ID)
-modal_cfg = entry.modal
-if modal_cfg is None:
-    raise RuntimeError("Modal configuration missing for task app {entry.app_id}")
-
 app = App(MODAL_APP_NAME)
 
 @app.function(
@@ -1091,17 +3066,69 @@ app = App(MODAL_APP_NAME)
 )
 @asgi_app()
 def fastapi_app():
+    # Import the module to trigger registration (inside container)
+    import os
+    # Prefer mounted source over any preinstalled site-packages version
+    import sys as _sys
+    for k in list(_sys.modules.keys()):
+        if k == 'synth_ai' or k.startswith('synth_ai.'):
+            _sys.modules.pop(k, None)
+    import importlib as _importlib
+    _importlib.invalidate_caches()
+    try:
+        if MODULE_FILE and os.path.exists(MODULE_FILE):
+            spec = importlib.util.spec_from_file_location(MODULE_NAME or 'task_app_module', MODULE_FILE)
+            if not spec or not spec.loader:
+                raise RuntimeError("Failed to prepare spec for: " + str(MODULE_FILE))
+            mod = importlib.util.module_from_spec(spec)
+            sys.modules[MODULE_NAME or 'task_app_module'] = mod
+            spec.loader.exec_module(mod)
+        else:
+            try:
+                importlib.import_module(MODULE_NAME)
+            except Exception:
+                fallback_file = '/opt/synth_ai_repo/__local_task_app__/' + (MODULE_NAME.split('.')[-1] if MODULE_NAME else 'task_app') + '.py'
+                if os.path.exists(fallback_file):
+                    spec = importlib.util.spec_from_file_location(MODULE_NAME or 'task_app_module', fallback_file)
+                    if not spec or not spec.loader:
+                        raise RuntimeError("Failed to prepare fallback spec for: " + str(fallback_file))
+                    mod = importlib.util.module_from_spec(spec)
+                    sys.modules[MODULE_NAME or 'task_app_module'] = mod
+                    spec.loader.exec_module(mod)
+                else:
+                    raise
+    except Exception as e:
+        raise RuntimeError("Task app import failed: " + str(e))
+
+    # Get the entry from registry (now that it's registered)
+    from synth_ai.task.apps import registry
+    from synth_ai.task.server import create_task_app
+    entry = registry.get(ENTRY_ID)
+    cfg = entry.modal
+    if cfg is None:
+        raise RuntimeError("Modal configuration missing for task app " + ENTRY_ID)
     config = entry.config_factory()
     return create_task_app(config)
 """
 
-    tmp = tempfile.NamedTemporaryFile("w", suffix=f"_{entry.app_id}_modal.py", delete=False)
-    tmp.write(script)
-    tmp.flush()
-    tmp.close()
-    return Path(tmp.name)
+    with tempfile.NamedTemporaryFile("w", suffix=f"_{entry.app_id}_modal.py", delete=False) as tmp:
+        tmp.write(script)
+        tmp.flush()
+        name = tmp.name
+    return Path(name)
 
 
 def register(cli: click.Group) -> None:
     cli.add_command(serve_command)
     cli.add_command(task_app_group)
+    cli.add_command(eval_command)
+    cli.add_command(filter_command)
+
+
+eval_command = eval_core.command
+
+filter_command = filter_core.command
+
+
+def register_eval(cli: click.Group) -> None:
+    cli.add_command(eval_command)