@pentoshi/clai 3.8.19 → 3.8.21

package/README.md

@@ -220,7 +220,7 @@ Coding and general sysadmin work use the same agent (scaffold, debug, packages)
 | Provider | Default model | Free tier | Key prefix |
 |----------|---------------|-----------|------------|
 | Groq | `llama-3.3-70b-versatile` | ✓ | `gsk_` |
-| Gemini | `gemini-2.0-flash` | ✓ | `AIza` |
+| Gemini | `gemini-2.0-flash` | ✓ | `AIza` / `AQ.` |
 | OpenRouter | `meta-llama/llama-3.3-70b-instruct:free` | ✓ | `sk-or-` |
 | OpenAI | `gpt-4o-mini` | — | `sk-` |
 | Anthropic | `claude-3-5-haiku-latest` | — | `sk-ant-` |
@@ -232,16 +232,19 @@ Coding and general sysadmin work use the same agent (scaffold, debug, packages)
 | Bynara | `mimo-v2.5-free` | ✓ | `sk_nry_` |
 
 ```sh
-clai set groq gsk_...
+clai set groq gsk_...              # store / append an API key (multi-key supported)
+clai set groq gsk_another_...      # add a second key for the same provider
 clai set gemini --from-env GEMINI_API_KEY
 echo "gsk_..." | clai set groq --stdin
 clai set ollama --url http://localhost:11434
-clai keys
+clai keys                          # lists each key (masked) + sticky active ★
 clai use groq
-clai provider          # picker shows selected model per provider
-clai unset groq
+clai provider                      # picker shows selected model per provider
+clai unset groq                    # removes ALL keys for that provider
 ```
 
+In the TUI, **`/set`** opens a multi-row key editor (like `/scope`): add with `+`, remove rows, **Save**, or **Reset all**. **`/unset`** clears every key for the chosen provider. When several keys are stored, clai **rotates** on rate limits / auth / transient errors (one retry per key, then the next key in a circle) and shows a non-stacking toast (`using groq · …ab12` / `switching …`).
+
 Env overrides: `GROQ_API_KEY`, `GEMINI_API_KEY`, `OPENROUTER_API_KEY`, `OPENAI_API_KEY`, `ANTHROPIC_API_KEY`, `NVIDIA_API_KEY`, `OLLAMA_HOST`, …
 
 ---

package/dist/agent/compaction-summary.d.ts

@@ -2,7 +2,7 @@
  * Prompts and helpers for LLM-based context compaction.
  * The model produces structured continuation memory — not a raw transcript dump.
  */
-export declare const COMPACTION_SYSTEM_PROMPT = "You are a session-memory compressor for an autonomous coding and security agent.\n\nWrite a dense, accurate CONTINUATION MEMORY for another assistant that will resume this work with no other history.\n\nRules:\n- Fidelity over style. Never invent tool results, file contents, findings, URLs, ports, or completions.\n- Prefer concrete artifacts: absolute paths, commands (short form), exit outcomes, HTTP status, plan task ids/states, job ids, open ports, confirmed vs unconfirmed findings.\n- Omit secrets, API keys, passwords, tokens, and full credential material. Say \"[redacted]\" if present.\n- Omit progress bars, repeated failures, and decorative chatter.\n- Do not wrap the whole answer in markdown code fences.\n- If something is unknown, omit it rather than guessing.\n- PHASE AWARENESS: Temporary UI/mode gates (plan-mode gather-only, \"await accept\", \"do not implement yet\") are HISTORICAL context \u2014 never rewrite them as permanent forever-rules for the resuming agent. Durable user/engagement policy (scope, non-destructive default, stay on remote target when that is the engagement) may still apply.";
+export declare const COMPACTION_SYSTEM_PROMPT = "You are a session-memory compressor for an autonomous coding and security agent.\n\nWrite a dense, accurate CONTINUATION MEMORY for another assistant that will resume this work with no other history.\n\nRules:\n- Fidelity over style. Never invent tool results, file contents, findings, URLs, ports, or completions.\n- Prefer concrete artifacts: absolute paths, commands (short form), exit outcomes, HTTP status, plan task ids/states, job ids, open ports, confirmed vs unconfirmed findings.\n- LENGTH: aim for ~800\u20131500 tokens of dense bullets \u2014 complete short memory beats a long dump that cuts mid-sentence. No full tool transcripts or HTML bodies.\n- Omit secrets, API keys, passwords, tokens, and full credential material. Say \"[redacted]\" if present.\n- Omit progress bars, repeated failures, and decorative chatter.\n- Do not wrap the whole answer in markdown code fences.\n- If something is unknown, omit it rather than guessing.\n- PHASE AWARENESS: Temporary UI/mode gates (plan-mode gather-only, \"await accept\", \"do not implement yet\") are HISTORICAL context \u2014 never rewrite them as permanent forever-rules for the resuming agent. Durable user/engagement policy (scope, non-destructive default, stay on remote target when that is the engagement) may still apply.";
 export interface CompactionPromptParts {
     visualTranscript?: string | undefined;
     messageTranscript: string;

package/dist/agent/compaction-summary.js

@@ -9,6 +9,7 @@ Write a dense, accurate CONTINUATION MEMORY for another assistant that will resu
 Rules:
 - Fidelity over style. Never invent tool results, file contents, findings, URLs, ports, or completions.
 - Prefer concrete artifacts: absolute paths, commands (short form), exit outcomes, HTTP status, plan task ids/states, job ids, open ports, confirmed vs unconfirmed findings.
+- LENGTH: aim for ~800–1500 tokens of dense bullets — complete short memory beats a long dump that cuts mid-sentence. No full tool transcripts or HTML bodies.
 - Omit secrets, API keys, passwords, tokens, and full credential material. Say "[redacted]" if present.
 - Omit progress bars, repeated failures, and decorative chatter.
 - Do not wrap the whole answer in markdown code fences.
@@ -29,12 +30,12 @@ export function buildCompactionUserPrompt(parts) {
     }
     const sections = [];
     if (planImplement) {
-        sections.push("Create a complete but compact HANDOFF MEMORY from PLAN-MODE RESEARCH for an agent that will EXECUTE the accepted plan next.", "The material below was gathered mostly under plan mode (research/roadmap). The next phase is agent implement — not gather-only.", "", "Organize under these exact section headings (skip a section only if empty):", "## User goals", "## Research evidence (facts from plan-mode tools)", "## Durable engagement rules (still apply in agent mode)", "## Plan-mode-only notes (historical — not current agent gates)", "## Commands/tools and results", "## Current state", "## Remaining work (post-accept tasks)", "## Open risks / failures", "", "CRITICAL separation:", "- Put EVIDENCE in Research evidence: targets, stack, ports, findings, artifact paths, OpenAPI notes, credentials status.", "- Durable engagement rules ONLY if they still bind implement (e.g. stay on remote target/scope, authorized testing, non-destructive default, do not treat clai workspace as the target).", "- Plan-mode-only notes: gather-only, await accept, do not exploit/implement yet, scaffold/write freezes that applied BEFORE accept. Label them explicitly as historical plan-mode — the implementer is past that phase.", "- Do NOT list plan-mode gather-only / read-only / no-mutate gates as if they still block approved task execution.", "- Live ACTIVE PLAN + task states will be re-injected separately; still preserve task progress and what research already covered so work is not repeated blindly.", "", "Preserve: recon evidence, fingerprinted stack, confirmed vs unconfirmed findings,", "targets/hosts in scope, credential/auth status, interesting features still to test,", "artifact paths, and anything the implementer needs that is not already in the live plan document.");
+        sections.push("Create a complete but compact HANDOFF MEMORY from PLAN-MODE RESEARCH for an agent that will EXECUTE the accepted plan next.", "Open with one framing line: this context is from plan mode — the research run that produced the comprehensive detailed plan and tasks the implementer is seeing (ACTIVE PLAN is re-injected separately).", "The material below was gathered under plan mode to design that plan/tasks. The next phase is agent implement — not gather-only.", "The live ACTIVE PLAN (goal/detail/tasks) will be re-injected separately — your job is ACTIONABLE research memory so implement does not re-discover or miss coverage.", "", "Organize under these exact section headings (include a section even if short — write \"none\" only when truly empty):", "## User goals", "## Research evidence (facts from plan-mode tools)", "## Coverage ledger (do not blindly re-do)", "## Confirmed findings", "## Negative / tested-OK results", "## Untested / open classes", "## Artifacts & paths", "## Durable engagement rules (still apply in agent mode)", "## Plan-mode-only notes (historical — not current agent gates)", "## Commands/tools and key results", "## Current state", "## Remaining work (post-accept tasks)", "## Open risks / failures", "", "How to fill sections (agent-performance critical):", "- Research evidence: concrete facts only — hosts/IPs, ports, stack fingerprint, auth surfaces, headers, endpoints, versions. Complete every bullet (never end mid-token like \"DEN\" for DENY).", "- Coverage ledger: what recon/enum is already done enough (e.g. DNS done, top-ports done, OpenAPI harvested) so implement can deepen rather than restart from zero.", "- Confirmed findings: each as severity + one-line evidence + impact/repro if known (F1, F2, … or short titles). If none yet, say so.", "- Negative / tested-OK: things checked and not issues (SSRF guard, CORS locked, etc.) so implement does not re-burn steps.", "- Untested / open classes: authz/IDOR, RBAC, payment, injection, etc. still open — especially anything blocked on credentials.", "- Artifacts & paths: absolute paths to reports, downloads, .map extracts, scan outputs under temp/scratch/.clai/outputs.", "- Durable engagement rules ONLY if they still bind implement (remote target/scope, authorized testing, non-destructive default, do not treat clai workspace as the target, no local dev server for remote assessments).", "- Plan-mode-only notes: gather-only / await-accept / no-exploit-yet gates that applied BEFORE accept — label historical; implementer is past that phase.", "- Commands/tools: high-signal tools used + outcomes (not every progress line). Prefer name + target + result in one line.", "- Remaining work: map to task ids/titles when ACTIVE PLAN is in DURABLE STATE (t1…); note blocked-on-creds clearly.", "- Do NOT invent findings. Do NOT omit confirmed issues that appear in the material. Prefer denser bullets over long prose.", "- Prefer COMPLETE short memory over a long memory that cuts off mid-sentence.");
     }
     else {
         sections.push("Create a complete but compact continuation memory of the session below.", "Treat resumed history and newer turns as one continuous conversation.", "", "Organize under these exact section headings (skip a section only if empty):", "## User goals", "## Decisions and constraints", "## Work completed", "## Commands/tools and results", "## Current state", "## Remaining work", "## Open risks / failures", "", "Preserve: user intentions, decisions, constraints, paths, stack/package manager,", "commands and key results, plan task states, errors and failed approaches,", "servers/jobs still running, and exactly what remains.", "", "PHASE AWARENESS under Decisions and constraints:", "- If earlier turns were plan-mode research, do not elevate gather-only / await-accept / no-implement rules as permanent forever-constraints for agent execution.", "- Durable engagement policy (scope, remote target, non-destructive default) may still be listed as current.", "- Prefer labeling historical plan-mode gates as \"(plan-mode only; superseded after accept)\" when they appear in the material.");
     }
-    sections.push("Be concise but specific. No secrets. No fabricated successes.");
+    sections.push("Be concise but specific. Target ~800–1500 tokens of memory. Dense bullets over prose. No secrets. No fabricated successes. No full tool dumps.");
     if (durable) {
         sections.push("", "DURABLE STATE (trust this over older chatter):", durable);
     }

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@@ -1 +1 @@
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package/dist/agent/context-breakdown.d.ts

@@ -0,0 +1,37 @@
+/**
+ * Estimate how a model request's context is composed (system / history / tools).
+ * Metadata-only: no prompt text is stored — only role counts and token estimates.
+ *
+ * Used for reliability ops and regression harnesses. Does not truncate context.
+ */
+import type { ChatMessage, ToolDefinition } from "../types.js";
+export interface ContextBreakdown {
+    /** Rough total estimated tokens for messages (+ tools if provided). */
+    readonly estimatedTotalTokens: number;
+    readonly systemTokens: number;
+    readonly userTokens: number;
+    readonly assistantTokens: number;
+    readonly toolResultTokens: number;
+    readonly toolSchemaTokens: number;
+    readonly messageCount: number;
+    readonly systemMessageCount: number;
+    readonly userMessageCount: number;
+    readonly assistantMessageCount: number;
+    readonly toolMessageCount: number;
+    /** High-level system subsections when detected by prefix. */
+    readonly systemParts: {
+        readonly constitutionTokens: number;
+        readonly planTokens: number;
+        readonly scopeTokens: number;
+        readonly sessionStateTokens: number;
+        readonly compactionMemoryTokens: number;
+        readonly otherSystemTokens: number;
+    };
+    readonly toolDefinitionCount: number;
+}
+/**
+ * Build a metadata-only breakdown of an assembled completion request.
+ */
+export declare function buildContextBreakdown(messages: readonly ChatMessage[], tools?: readonly ToolDefinition[] | undefined): ContextBreakdown;
+/** Flatten for audit/diagnostic logs (numeric keys only — no content). */
+export declare function contextBreakdownAuditPayload(breakdown: ContextBreakdown): Record<string, number>;

package/dist/agent/context-breakdown.js

@@ -0,0 +1,145 @@
+/**
+ * Estimate how a model request's context is composed (system / history / tools).
+ * Metadata-only: no prompt text is stored — only role counts and token estimates.
+ *
+ * Used for reliability ops and regression harnesses. Does not truncate context.
+ */
+import { estimateMessagesTokens, estimateTokens, isCompactionMemoryMessage, COMPACTION_MEMORY_PREFIX, PLAN_IMPLEMENT_MEMORY_PREFIX, MECHANICAL_MEMORY_PREFIX, } from "./context-manager.js";
+import { SESSION_STATE_PREFIX } from "./session-state.js";
+function isPlanSystem(content) {
+    return content.startsWith("ACTIVE PLAN") || content.includes("\nACTIVE PLAN");
+}
+function isScopeSystem(content) {
+    return (content.startsWith("ENGAGEMENT SCOPE") ||
+        content.includes("\nENGAGEMENT SCOPE"));
+}
+function isSessionStateSystem(content) {
+    return (content.startsWith(SESSION_STATE_PREFIX) ||
+        content.includes(SESSION_STATE_PREFIX));
+}
+function isCompactionSystem(content) {
+    return (content.startsWith(COMPACTION_MEMORY_PREFIX) ||
+        content.startsWith(PLAN_IMPLEMENT_MEMORY_PREFIX) ||
+        content.startsWith(MECHANICAL_MEMORY_PREFIX) ||
+        // Message-shaped helper when role is system.
+        isCompactionMemoryMessage({ role: "system", content }));
+}
+/**
+ * Build a metadata-only breakdown of an assembled completion request.
+ */
+export function buildContextBreakdown(messages, tools) {
+    let systemTokens = 0;
+    let userTokens = 0;
+    let assistantTokens = 0;
+    let toolResultTokens = 0;
+    let systemMessageCount = 0;
+    let userMessageCount = 0;
+    let assistantMessageCount = 0;
+    let toolMessageCount = 0;
+    let constitutionTokens = 0;
+    let planTokens = 0;
+    let scopeTokens = 0;
+    let sessionStateTokens = 0;
+    let compactionMemoryTokens = 0;
+    let otherSystemTokens = 0;
+    for (const message of messages) {
+        const tokens = estimateTokens(message.content) + 4;
+        switch (message.role) {
+            case "system": {
+                systemMessageCount += 1;
+                systemTokens += tokens;
+                if (isCompactionSystem(message.content)) {
+                    compactionMemoryTokens += tokens;
+                }
+                else if (isPlanSystem(message.content)) {
+                    planTokens += tokens;
+                }
+                else if (isScopeSystem(message.content)) {
+                    scopeTokens += tokens;
+                }
+                else if (isSessionStateSystem(message.content)) {
+                    sessionStateTokens += tokens;
+                }
+                else if (systemMessageCount === 1 ||
+                    /CURRENT MODE:|OUTCOME CONTRACT|# ROLE|# HONESTY/i.test(message.content)) {
+                    // Primary system / composed constitution (often message[0]).
+                    constitutionTokens += tokens;
+                }
+                else {
+                    otherSystemTokens += tokens;
+                }
+                break;
+            }
+            case "user":
+                userMessageCount += 1;
+                userTokens += tokens;
+                break;
+            case "assistant":
+                assistantMessageCount += 1;
+                assistantTokens += tokens;
+                if (message.toolCalls?.length) {
+                    assistantTokens += estimateTokens(JSON.stringify(message.toolCalls));
+                }
+                break;
+            case "tool":
+                toolMessageCount += 1;
+                toolResultTokens += tokens;
+                break;
+            default:
+                otherSystemTokens += tokens;
+                break;
+        }
+    }
+    let toolSchemaTokens = 0;
+    const toolDefinitionCount = tools?.length ?? 0;
+    if (tools?.length) {
+        toolSchemaTokens = estimateTokens(JSON.stringify(tools));
+    }
+    const estimatedTotalTokens = estimateMessagesTokens([...messages]) + toolSchemaTokens;
+    return {
+        estimatedTotalTokens,
+        systemTokens,
+        userTokens,
+        assistantTokens,
+        toolResultTokens,
+        toolSchemaTokens,
+        messageCount: messages.length,
+        systemMessageCount,
+        userMessageCount,
+        assistantMessageCount,
+        toolMessageCount,
+        systemParts: {
+            constitutionTokens,
+            planTokens,
+            scopeTokens,
+            sessionStateTokens,
+            compactionMemoryTokens,
+            otherSystemTokens,
+        },
+        toolDefinitionCount,
+    };
+}
+/** Flatten for audit/diagnostic logs (numeric keys only — no content). */
+export function contextBreakdownAuditPayload(breakdown) {
+    return {
+        estimatedTotalTokens: breakdown.estimatedTotalTokens,
+        systemTokens: breakdown.systemTokens,
+        userTokens: breakdown.userTokens,
+        assistantTokens: breakdown.assistantTokens,
+        toolResultTokens: breakdown.toolResultTokens,
+        toolSchemaTokens: breakdown.toolSchemaTokens,
+        messageCount: breakdown.messageCount,
+        systemMessageCount: breakdown.systemMessageCount,
+        userMessageCount: breakdown.userMessageCount,
+        assistantMessageCount: breakdown.assistantMessageCount,
+        toolMessageCount: breakdown.toolMessageCount,
+        constitutionTokens: breakdown.systemParts.constitutionTokens,
+        planTokens: breakdown.systemParts.planTokens,
+        scopeTokens: breakdown.systemParts.scopeTokens,
+        sessionStateTokens: breakdown.systemParts.sessionStateTokens,
+        compactionMemoryTokens: breakdown.systemParts.compactionMemoryTokens,
+        otherSystemTokens: breakdown.systemParts.otherSystemTokens,
+        toolDefinitionCount: breakdown.toolDefinitionCount,
+    };
+}
+//# sourceMappingURL=context-breakdown.js.map

package/dist/agent/context-breakdown.js.map

@@ -0,0 +1 @@
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package/dist/agent/context-manager.d.ts

@@ -11,8 +11,23 @@ export declare function estimateMessagesTokens(messages: ChatMessage[]): number;
 /**
  * Agent-loop auto-compact threshold (estimated tokens). Shared with `/context`
  * so the reported % of budget matches when auto-compaction fires.
+ *
+ * 100k (was 150k): thinking models balloon context; implement turns with large
+ * tool artifacts hit mid-100k before the old threshold and then fail streams.
+ * Earlier compact keeps implement/plan loops healthier without constant /compact.
+ */
+export declare const AUTO_COMPACT_TOKEN_BUDGET = 100000;
+/**
+ * Soft post-compact band we *prefer* (includes system prompt ~8k).
+ * Achieved by dense memory + progressive soft-trim of oversized dumps only.
+ * Never a reject gate, never drops messages/tool pairs to hit the number.
  */
-export declare const AUTO_COMPACT_TOKEN_BUDGET = 150000;
+export declare const POST_COMPACT_SOFT_GUIDANCE_TOKENS = 16000;
+/** Prefer landing at or under this; still accept if content needs more room. */
+export declare const POST_COMPACT_SOFT_UPPER_BAND_TOKENS = 20000;
+/** Auto-compact: reject empty/near-empty memory after large history (amnesia). */
+export declare const AUTO_COMPACT_STUB_MIN_CHARS = 120;
+export declare const AUTO_COMPACT_STUB_BEFORE_TOKENS = 20000;
 export interface CompactOptions {
     /** Soft budget (tokens). When estimated tokens exceed this, compact. */
     budgetTokens?: number | undefined;
@@ -43,8 +58,9 @@ export declare const COMPACTION_MEMORY_PREFIX = "Session memory from compacted e
 /**
  * Plan-mode research handoff memory (pre-implement compact). Distinct so the
  * agent does not treat plan-mode gather-only history as permanent gates.
+ * Explicitly ties this context to the plan/tasks the implementer is seeing.
  */
-export declare const PLAN_IMPLEMENT_MEMORY_PREFIX = "Session memory from plan-mode research (handoff to agent implement \u2014 gather-only phase is over; execute approved tasks):";
+export declare const PLAN_IMPLEMENT_MEMORY_PREFIX = "Session memory from PLAN MODE research that was used to build the comprehensive detailed plan and tasks you are seeing now (handoff to agent implement \u2014 gather-only phase is over; execute approved tasks):";
 export declare const MECHANICAL_MEMORY_PREFIX = "Earlier turns in this session, summarized";
 export declare function isCompactionMemoryMessage(message: ChatMessage): boolean;
 /** Prefix used when writing a compacted memory system message. */
@@ -69,3 +85,14 @@ export declare function compactMessages(messages: ChatMessage[], options?: Compa
  * can report the failure and the original messages stay untouched.
  */
 export declare function compactMessagesWithSummary(messages: ChatMessage[], summarize: (prompt: string) => Promise<string>, options?: CompactOptions, sessionTranscript?: string | undefined): Promise<CompactResult>;
+/**
+ * Whether an auto-compact result is safe to apply.
+ * Only structural / quality gates — never "afterTokens must be under N".
+ */
+export declare function shouldApplyAutoCompact(input: {
+    summarized: boolean;
+    summaryBody: string;
+    beforeTokens: number;
+    afterTokens: number;
+    afterMessages: readonly ChatMessage[];
+}): boolean;

package/dist/agent/context-manager.js

@@ -1,6 +1,6 @@
 import { redactSecrets } from "../llm/provider.js";
 import { stripThinking } from "../ui/thinking.js";
-import { expandKeepStartForToolPairs } from "./tool-history.js";
+import { expandKeepStartForToolPairs, hasOrphanToolMessages, } from "./tool-history.js";
 import { buildCompactionUserPrompt, trimTranscriptForCompaction, } from "./compaction-summary.js";
 /**
  * Per-char token estimator. Real tokenization varies by provider, but for
@@ -26,10 +26,36 @@ export function estimateMessagesTokens(messages) {
 /**
  * Agent-loop auto-compact threshold (estimated tokens). Shared with `/context`
  * so the reported % of budget matches when auto-compaction fires.
+ *
+ * 100k (was 150k): thinking models balloon context; implement turns with large
+ * tool artifacts hit mid-100k before the old threshold and then fail streams.
+ * Earlier compact keeps implement/plan loops healthier without constant /compact.
+ */
+export const AUTO_COMPACT_TOKEN_BUDGET = 100_000;
+/**
+ * Soft post-compact band we *prefer* (includes system prompt ~8k).
+ * Achieved by dense memory + progressive soft-trim of oversized dumps only.
+ * Never a reject gate, never drops messages/tool pairs to hit the number.
+ */
+export const POST_COMPACT_SOFT_GUIDANCE_TOKENS = 16_000;
+/** Prefer landing at or under this; still accept if content needs more room. */
+export const POST_COMPACT_SOFT_UPPER_BAND_TOKENS = 20_000;
+/**
+ * Progressive soft-trim tiers for the kept tail. Start generous; only step
+ * tighter if estimate is still above the soft upper band. Never blanks a
+ * message or removes tool pairs.
  */
-export const AUTO_COMPACT_TOKEN_BUDGET = 150_000;
+const TAIL_SOFT_TIERS = [
+    { tool: 6_000, assistant: 8_000, user: 8_000 },
+    { tool: 4_000, assistant: 5_000, user: 6_000 },
+    { tool: 2_500, assistant: 3_500, user: 4_000 },
+];
+/** Auto-compact: reject empty/near-empty memory after large history (amnesia). */
+export const AUTO_COMPACT_STUB_MIN_CHARS = 120;
+export const AUTO_COMPACT_STUB_BEFORE_TOKENS = 20_000;
 const DEFAULT_BUDGET_TOKENS = 32_000;
-const DEFAULT_KEEP_RECENT = 6;
+/** Default keepRecent for mechanical compact; LLM auto path uses 2 via runner. */
+const DEFAULT_KEEP_RECENT = 2;
 /**
  * Content prefixes that mark a `role:"system"` message as compacted session
  * memory (vs. the main system prompt or transient injected guidance). Exported
@@ -41,8 +67,9 @@ export const COMPACTION_MEMORY_PREFIX = "Session memory from compacted earlier t
 /**
  * Plan-mode research handoff memory (pre-implement compact). Distinct so the
  * agent does not treat plan-mode gather-only history as permanent gates.
+ * Explicitly ties this context to the plan/tasks the implementer is seeing.
  */
-export const PLAN_IMPLEMENT_MEMORY_PREFIX = "Session memory from plan-mode research (handoff to agent implement — gather-only phase is over; execute approved tasks):";
+export const PLAN_IMPLEMENT_MEMORY_PREFIX = "Session memory from PLAN MODE research that was used to build the comprehensive detailed plan and tasks you are seeing now (handoff to agent implement — gather-only phase is over; execute approved tasks):";
 export const MECHANICAL_MEMORY_PREFIX = "Earlier turns in this session, summarized";
 export function isCompactionMemoryMessage(message) {
     return (message.role === "system" &&
@@ -205,20 +232,26 @@ export async function compactMessagesWithSummary(messages, summarize, options =
         throw new Error("compaction failed: model returned an empty summary");
     }
     const head = start === 1 ? [messages[0]] : [];
-    // Strip <think> tags from tail messages so thinking content never
-    // survives compaction into the model's context.
-    const tail = messages.slice(tailStart).map((msg) => {
-        if (msg.role === "assistant" && /<think/i.test(msg.content)) {
-            return { ...msg, content: stripThinking(msg.content).visible };
-        }
-        return msg;
-    });
+    const rawTail = messages.slice(tailStart);
     const memoryPrefix = compactionMemoryPrefixForPurpose(options.purpose);
-    const compacted = [
-        ...head,
-        { role: "system", content: `${memoryPrefix}\n\n${summary}` },
-        ...tail,
-    ];
+    const memoryMsg = {
+        role: "system",
+        content: `${memoryPrefix}\n\n${summary}`,
+    };
+    // Prefer ~16–20k: start with a generous lean tail, then progressively
+    // soft-trim oversized dumps only while still over the soft upper band.
+    // Never drop messages or tool pairs. If still high after last tier, accept.
+    let compacted = buildLeanCompact(head, memoryMsg, rawTail, TAIL_SOFT_TIERS[0]);
+    for (let i = 1; i < TAIL_SOFT_TIERS.length; i += 1) {
+        if (estimateMessagesTokens(compacted) <= POST_COMPACT_SOFT_UPPER_BAND_TOKENS) {
+            break;
+        }
+        compacted = buildLeanCompact(head, memoryMsg, rawTail, TAIL_SOFT_TIERS[i]);
+    }
+    // Structural safety only — never reject because afterTokens > soft band.
+    if (hasOrphanToolMessages(compacted)) {
+        throw new Error("compaction failed: would produce orphan tool messages — keeping full history");
+    }
     const afterTokens = estimateMessagesTokens(compacted);
     return {
         messages: compacted,
@@ -229,6 +262,81 @@ export async function compactMessagesWithSummary(messages, summarize, options =
         summarized: true,
     };
 }
+function buildLeanCompact(head, memoryMsg, rawTail, preferMax) {
+    return [...head, memoryMsg, ...leanTailMessages(rawTail, preferMax)];
+}
+/**
+ * Whether an auto-compact result is safe to apply.
+ * Only structural / quality gates — never "afterTokens must be under N".
+ */
+export function shouldApplyAutoCompact(input) {
+    if (!input.summarized)
+        return false;
+    // Must actually shrink (otherwise pointless and can thrash).
+    if (input.afterTokens >= input.beforeTokens)
+        return false;
+    if (hasOrphanToolMessages([...input.afterMessages]))
+        return false;
+    const body = input.summaryBody.trim();
+    if (!body)
+        return false;
+    // Amnesia stub only — not a target-size check.
+    if (input.beforeTokens >= AUTO_COMPACT_STUB_BEFORE_TOKENS &&
+        body.length < AUTO_COMPACT_STUB_MIN_CHARS) {
+        return false;
+    }
+    return true;
+}
+function isStaleDurableSystem(content) {
+    return (content.startsWith("ACTIVE PLAN") ||
+        content.startsWith("SESSION STATE") ||
+        content.startsWith("ENGAGEMENT SCOPE") ||
+        content.startsWith("TASK ANALYSIS") ||
+        content.includes("SESSION STATE / WORKING MEMORY"));
+}
+/** Soft head+tail prefer — only when a single message is huge waste. */
+function preferTrimContent(text, preferMax) {
+    if (text.length <= preferMax)
+        return text;
+    const half = Math.floor((preferMax - 48) / 2);
+    if (half < 120)
+        return text; // don't mangle medium messages
+    return `${text.slice(0, half)}\n…(trimmed oversized dump in compact tail; full may be on disk)…\n${text.slice(-half)}`;
+}
+function leanTailMessages(tail, preferMax) {
+    return tail
+        .filter((msg) => {
+        // Fresh plan/session are re-injected after compact — drop stale copies.
+        if (msg.role === "system" && isStaleDurableSystem(msg.content)) {
+            return false;
+        }
+        // Drop prior compaction memory from the tail (new memory is the prefix).
+        if (isCompactionMemoryMessage(msg))
+            return false;
+        return true;
+    })
+        .map((msg) => {
+        if (msg.role === "tool") {
+            return { ...msg, content: preferTrimContent(msg.content, preferMax.tool) };
+        }
+        if (msg.role === "assistant") {
+            const visible = /<think/i.test(msg.content)
+                ? stripThinking(msg.content).visible
+                : msg.content;
+            return {
+                ...msg,
+                content: preferTrimContent(visible, preferMax.assistant),
+            };
+        }
+        if (msg.role === "user") {
+            return {
+                ...msg,
+                content: preferTrimContent(msg.content, preferMax.user),
+            };
+        }
+        return msg;
+    });
+}
 function oneLine(text, maxChars) {
     const cleaned = text.replace(/\s+/g, " ").trim();
     if (cleaned.length <= maxChars)

package/dist/agent/context-manager.js.map

@@ -1 +1 @@
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package/dist/agent/continue-orient.d.ts

@@ -0,0 +1,39 @@
+/**
+ * Soft orientation for continue / mid-work recovery after interruptions.
+ *
+ * Professional agents (Claude Code, Cursor, etc.) re-attach to interrupted
+ * work: live jobs, open tasks, last tools — they do not skip ahead and mark
+ * plan items done. This is guidance + facts, not a hard gate.
+ */
+import type { SessionPlan } from "../store/plan.js";
+import type { ChatMessage } from "../types.js";
+import type { BackgroundJob } from "../tools/jobs.js";
+export declare const CONTINUE_ORIENT_PREFIX = "CONTINUE / RECOVER MID-WORK";
+/** User is asking to pick up after a pause, error, or short nudge. */
+export declare function looksLikeContinueOrResumePrompt(prompt: string): boolean;
+export interface ContinueOrientInput {
+    readonly prompt: string;
+    readonly history?: readonly ChatMessage[] | undefined;
+    readonly plan?: SessionPlan | undefined;
+    readonly runningJobs?: readonly BackgroundJob[] | undefined;
+    readonly recentJobs?: readonly BackgroundJob[] | undefined;
+    /** Skip for pure Q&A / social — never force re-attach on "what did you find?" */
+    readonly informationalQuery?: boolean | undefined;
+    readonly idleOrSocial?: boolean | undefined;
+}
+export interface RecentToolHint {
+    readonly name: string;
+    readonly ok?: boolean | undefined;
+    readonly head: string;
+}
+/** Last few tool results from history (newest last), high-signal one-liners. */
+export declare function extractRecentToolHints(history: readonly ChatMessage[] | undefined, limit?: number): RecentToolHint[];
+/**
+ * Whether this turn should receive mid-work recovery orientation.
+ * Soft: continue phrasing, or open plan work / live jobs with prior history.
+ */
+export declare function shouldInjectContinueOrientation(input: ContinueOrientInput): boolean;
+/**
+ * Factual briefing + soft procedure. Empty string if nothing useful to say.
+ */
+export declare function buildContinueOrientation(input: ContinueOrientInput): string;