@vellumai/assistant 0.8.8 → 0.8.9-dev.202606091853.fbaa2ae

package/src/daemon/conversation-error.ts

@@ -150,11 +150,25 @@ const STREAMING_ERROR_PATTERNS = [
 ];
 
 // User-initiated cancellation patterns — these should NOT produce conversation_error
-// Image-input validation patterns — Anthropic 400s with this message when an image
-// block exceeds the per-side pixel cap. Distinct classification matters because
-// retrying with the same oversized image is futile; the user needs to resize.
+// Image-input validation patterns — Anthropic 400s with one of these messages
+// when an image block violates a hard limit. The first matches the per-side
+// pixel cap ("image dimensions exceed max allowed size"); the second matches the
+// base64 payload cap ("image exceeds 5 MB maximum: 7465044 bytes > 5242880
+// bytes"). Distinct classification matters because retrying with the same
+// oversized image is futile — the recovery path must strip or downscale it.
 const IMAGE_DIMENSIONS_TOO_LARGE_PATTERNS = [
   /image dimensions? exceeds? max allowed size/i,
+  /image exceeds \d+\s*MB maximum/i,
+];
+
+const VISION_NOT_SUPPORTED_PATTERNS = [
+  /no endpoints found that support image input/i,
+  /does not support image/i,
+  /doesn't support image input/i,
+  /image input is not supported/i,
+  /this model does not support vision/i,
+  /vision is not supported/i,
+  /multi-?modal.*not.*support/i,
 ];
 
 const CANCEL_PATTERNS = [/abort/i, /cancel/i];
@@ -447,11 +461,20 @@ function classifyCore(
         return {
           code: "IMAGE_TOO_LARGE",
           userMessage:
-            "An attached image is too large for the AI provider — image dimensions must be under 8000 pixels per side. Resize the image and try again.",
+            "An image in this conversation was too large for the AI provider and was automatically reduced. Send your message again to continue.",
           retryable: false,
           errorCategory: "image_dimensions_too_large",
         };
       }
+      if (isVisionNotSupported(message)) {
+        return {
+          code: "PROVIDER_API",
+          userMessage:
+            "This model doesn't support image input. Remove the image or switch to a vision-capable model.",
+          retryable: false,
+          errorCategory: "vision_not_supported",
+        };
+      }
       // Extract the provider detail after "API error (NNN): " prefix
       const detailMatch = message.match(/API error \(\d+\):\s*(.+)/i);
       const detail = detailMatch?.[1];
@@ -481,6 +504,10 @@ function isImageDimensionsTooLarge(message: string): boolean {
   return IMAGE_DIMENSIONS_TOO_LARGE_PATTERNS.some((p) => p.test(message));
 }
 
+function isVisionNotSupported(message: string): boolean {
+  return VISION_NOT_SUPPORTED_PATTERNS.some((p) => p.test(message));
+}
+
 /** Check whether an error message indicates a web-search-specific ordering failure. */
 function isWebSearchOrderingError(message: string): boolean {
   return WEB_SEARCH_ORDERING_PATTERNS.some((p) => p.test(message));

package/src/daemon/conversation-history.ts

@@ -1,6 +1,5 @@
 import { v4 as uuid } from "uuid";
 
-import { getSummaryFromContextMessage } from "../context/window-manager.js";
 import {
   deleteLastExchange,
   deleteMessageById,
@@ -13,6 +12,7 @@ import { enqueueMemoryJob } from "../memory/jobs-store.js";
 import { relinkLlmRequestLogs } from "../memory/llm-request-log-store.js";
 import { withQdrantBreaker } from "../memory/qdrant-circuit-breaker.js";
 import { getQdrantClient } from "../memory/qdrant-client.js";
+import { getSummaryFromContextMessage } from "../plugins/defaults/compaction/window-manager.js";
 import type { ContentBlock, Message } from "../providers/types.js";
 import { getLogger } from "../util/logger.js";
 import { truncate } from "../util/truncate.js";

package/src/daemon/conversation-lifecycle.ts

@@ -1,23 +1,20 @@
 /**
- * Conversation lifecycle methods extracted from Conversation: loadFromDb, abort,
- * and dispose. Each operates on a context interface so the Conversation class
+ * Conversation lifecycle helpers extracted from Conversation: abort and
+ * dispose. Each operates on a context interface so the Conversation class
  * can delegate without exposing its full surface.
  */
 
 import { getConfig } from "../config/loader.js";
-import { createContextSummaryMessage } from "../context/window-manager.js";
 import type { EventBus } from "../events/bus.js";
 import type { AssistantDomainEvents } from "../events/domain-events.js";
 import type { ToolProfiler } from "../events/tool-profiling-listener.js";
 import { enqueueAutoAnalysisIfEnabled } from "../memory/auto-analysis-enqueue.js";
 import { isAutoAnalysisConversation } from "../memory/auto-analysis-guard.js";
-import { getConversation, getMessages } from "../memory/conversation-crud.js";
 import { enqueueMemoryJob, isMemoryEnabled } from "../memory/jobs-store.js";
 import { enqueueMemoryRetrospectiveIfEnabled } from "../memory/memory-retrospective-enqueue.js";
-import { shouldExposePersonalMemory } from "../memory/v2/static-context.js";
 import type { PermissionPrompter } from "../permissions/prompter.js";
 import type { SecretPrompter } from "../permissions/secret-prompter.js";
-import { repairHistory } from "../plugins/defaults/history-repair/terminal.js";
+import { disposeContextWindowManager } from "../plugins/defaults/compaction/manager-store.js";
 import type { ContentBlock, Message } from "../providers/types.js";
 import {
   isUntrustedTrustClass,
@@ -28,15 +25,8 @@ import { type AbortReason, createAbortReason } from "../util/abort-reasons.js";
 import { getLogger } from "../util/logger.js";
 import { unregisterCallNotifiers } from "./conversation-notifiers.js";
 import type { MessageQueue } from "./conversation-queue-manager.js";
-import { stripInjectionsForCompaction } from "./conversation-runtime-assembly.js";
 import { resetSkillToolProjection } from "./conversation-skill-tools.js";
-import type {
-  SurfaceData,
-  SurfaceType,
-  UsageStats,
-} from "./message-protocol.js";
-import { filterMessagesForUntrustedActor } from "./message-provenance.js";
-import { resolveTrustClass, type TrustContext } from "./trust-context.js";
+import type { SurfaceData, SurfaceType } from "./message-protocol.js";
 
 const log = getLogger("conversation-lifecycle");
 
@@ -75,17 +65,6 @@ export function reinjectImageSourcePaths(
 
 // ── Context Interfaces ───────────────────────────────────────────────
 
-export interface LoadFromDbContext {
-  readonly conversationId: string;
-  messages: Message[];
-  usageStats: UsageStats;
-  contextCompactedMessageCount: number;
-  contextCompactedAt: number | null;
-  trustContext?: TrustContext;
-  loadedHistoryTrustClass?: TrustClass;
-  loadedHistoryPersonalMemoryAllowed?: boolean;
-}
-
 export interface AbortContext {
   readonly conversationId: string;
   isProcessing(): boolean;
@@ -127,236 +106,6 @@ export interface DisposeContext extends AbortContext {
   abort(): void;
 }
 
-// ── loadFromDb ───────────────────────────────────────────────────────
-
-export async function loadFromDb(ctx: LoadFromDbContext): Promise<void> {
-  const trustClass = ctx.trustContext?.trustClass;
-  const allDbMessages = getMessages(ctx.conversationId);
-  const dbMessages = isUntrustedTrustClass(trustClass)
-    ? filterMessagesForUntrustedActor(allDbMessages)
-    : allDbMessages;
-
-  const conv = getConversation(ctx.conversationId);
-  const contextSummary = !isUntrustedTrustClass(trustClass)
-    ? conv?.contextSummary?.trim() || null
-    : null;
-  if (isUntrustedTrustClass(trustClass)) {
-    // Compacted summaries may include trusted/guardian-only details, so we
-    // disable summary-based context for untrusted actor views.
-    ctx.contextCompactedMessageCount = 0;
-    ctx.contextCompactedAt = null;
-  } else {
-    ctx.contextCompactedMessageCount = Math.max(
-      0,
-      Math.min(conv?.contextCompactedMessageCount ?? 0, dbMessages.length),
-    );
-    ctx.contextCompactedAt = conv?.contextCompactedAt ?? null;
-  }
-
-  // Every injection-strip event (`/clean` or compaction) updates
-  // `historyStrippedAt`. Messages older than this should skip metadata
-  // rehydration and have any injection prefixes still embedded in their
-  // content stripped, so the post-strip view survives reload and forks.
-  const historyStrippedAt = conv?.historyStrippedAt ?? null;
-  const slicedDbMessages = dbMessages.slice(ctx.contextCompactedMessageCount);
-  let preStrippedCount = 0;
-  if (historyStrippedAt != null) {
-    const boundary = slicedDbMessages.findIndex(
-      (m) => m.createdAt >= historyStrippedAt,
-    );
-    preStrippedCount = boundary === -1 ? slicedDbMessages.length : boundary;
-  }
-
-  // Mirror the injection-time gate (`shouldExposePersonalMemory` in
-  // `conversation-agent-loop.ts`) so background/local conversations
-  // (sourceChannel `undefined` or `"vellum"`) can rehydrate the persisted
-  // v2 static memory block. Use `resolveTrustClass` for parity with the
-  // agent loop — it folds in the HTTP-auth-disabled dev bypass so
-  // rehydration and injection agree on the effective trust class.
-  const personalMemoryAllowed = shouldExposePersonalMemory({
-    sourceChannel: ctx.trustContext?.sourceChannel,
-    isTrustedActor: resolveTrustClass(ctx.trustContext) === "guardian",
-  });
-  const parsedMessages: Message[] = slicedDbMessages.map((m, index, arr) => {
-    const isPreStripped = index < preStrippedCount;
-    const role = m.role as "user" | "assistant";
-    let content: ContentBlock[];
-    try {
-      const parsed = JSON.parse(m.content);
-      content = Array.isArray(parsed)
-        ? parsed
-        : [{ type: "text", text: m.content }];
-    } catch {
-      log.warn(
-        { conversationId: ctx.conversationId, messageId: m.id },
-        "Invalid JSON in persisted message content, replacing with safe text block",
-      );
-      content = [{ type: "text", text: m.content }];
-    }
-
-    content = reinjectImageSourcePaths(content, role, m.metadata);
-
-    // Re-inject persisted injection blocks from metadata so it survives
-    // conversation reloads (eviction, restart, fork).
-    if (role === "user" && m.metadata && !isPreStripped) {
-      try {
-        const meta = JSON.parse(m.metadata);
-        const isTail = index === arr.length - 1;
-
-        // Rehydrate in reverse injection order (innermost block first)
-        // so the resulting layout matches `applyRuntimeInjections`'s
-        // after-memory-prefix splices in ascending injector order
-        // (pkb-context 30, pkb-reminder 35, memory-v2-static 38,
-        // now-md 40 — the v2 static block lands inside the memory
-        // prefix, so now-md splices *after* it):
-        //   [<workspace>, <turn_context>, <memory>dynamic</memory>,
-        //    <info>v2static</info>, <NOW.md>, <system_reminder>,
-        //    <knowledge_base>, ...original]
-        // The v2 static block is replayed verbatim from stored metadata,
-        // so rows may carry either `<info>…</info>` or `<memory>…</memory>`
-        // depending on when they were persisted.
-        // Required so Anthropic's prefix cache keeps matching msg[0]
-        // across daemon restart and conversation eviction. The tail
-        // row only rehydrates `memoryInjectedBlock` — the next turn
-        // re-injects the rest fresh.
-        if (!isTail && typeof meta.pkbContextBlock === "string") {
-          content = [
-            { type: "text" as const, text: meta.pkbContextBlock },
-            ...content,
-          ];
-        }
-
-        if (!isTail && typeof meta.pkbSystemReminderBlock === "string") {
-          content = [
-            { type: "text" as const, text: meta.pkbSystemReminderBlock },
-            ...content,
-          ];
-        }
-
-        if (!isTail && typeof meta.nowScratchpadBlock === "string") {
-          content = [
-            { type: "text" as const, text: meta.nowScratchpadBlock },
-            ...content,
-          ];
-        }
-
-        // The v2 static memory block (essentials/threads/recent/buffer
-        // wrapped in either `<info>…</info>` or `<memory>…</memory>`)
-        // carries personal user memory. Trust-gated to mirror
-        // `shouldExposePersonalMemory` at injection time — untrusted-actor
-        // views must not read persisted personal memory back through
-        // metadata. Skipped on the tail row because the next turn
-        // re-injects fresh content on full-mode turns.
-        if (
-          !isTail &&
-          personalMemoryAllowed &&
-          typeof meta.memoryV2StaticBlock === "string"
-        ) {
-          content = [
-            { type: "text" as const, text: meta.memoryV2StaticBlock },
-            ...content,
-          ];
-        }
-
-        // Memory remains rehydrated on all rows (existing behavior).
-        // Strip any pre-existing wrapper before re-wrapping so historical
-        // rows persisted with the wrapper (v2 path before the
-        // injectedBlockText contract was unified with v1's unwrapped form)
-        // don't render double-wrapped after rehydrate. Only unwrap when
-        // the full <memory>...</memory> pair is present so we don't mutate
-        // legitimate unwrapped payloads that happen to start with
-        // "<memory>\n" or end with "\n</memory>".
-        if (typeof meta.memoryInjectedBlock === "string") {
-          const block = meta.memoryInjectedBlock;
-          const inner =
-            block.startsWith("<memory>\n") && block.endsWith("\n</memory>")
-              ? block.slice("<memory>\n".length, -"\n</memory>".length)
-              : block;
-          content = [
-            {
-              type: "text" as const,
-              text: `<memory>\n${inner}\n</memory>`,
-            },
-            ...content,
-          ];
-        }
-
-        if (!isTail && typeof meta.turnContextBlock === "string") {
-          content = [
-            { type: "text" as const, text: meta.turnContextBlock },
-            ...content,
-          ];
-        }
-
-        if (!isTail && typeof meta.workspaceBlock === "string") {
-          content = [
-            { type: "text" as const, text: meta.workspaceBlock },
-            ...content,
-          ];
-        }
-      } catch {
-        /* ignore parse errors — metadata may be malformed */
-      }
-    }
-
-    return { role, content };
-  });
-
-  // Strip pre-clean messages only; post-clean messages keep the fresh
-  // injections they were generated with.
-  const messagesBeforeRepair =
-    preStrippedCount === 0
-      ? parsedMessages
-      : [
-          ...stripInjectionsForCompaction(
-            parsedMessages.slice(0, preStrippedCount),
-          ),
-          ...parsedMessages.slice(preStrippedCount),
-        ];
-
-  // Normalize the canonical persisted history once at load. Every consumer
-  // of `ctx.messages` outside the agent loop (history edit/undo, PKB context
-  // tracking, surfaces) reads this list directly, so it must satisfy the
-  // provider pairing/alternation rules before any of them run. The agent
-  // loop's pre-run repair only repairs the transient per-turn message list it
-  // sends to the provider and never writes back here, so this pass is not
-  // redundant with it.
-  const { messages: repairedMessages, stats } =
-    repairHistory(messagesBeforeRepair);
-  if (
-    stats.assistantToolResultsMigrated > 0 ||
-    stats.missingToolResultsInserted > 0 ||
-    stats.orphanToolResultsDowngraded > 0 ||
-    stats.consecutiveSameRoleMerged > 0
-  ) {
-    log.warn(
-      { conversationId: ctx.conversationId, phase: "load", ...stats },
-      "Repaired persisted history",
-    );
-  }
-  ctx.messages = repairedMessages;
-
-  if (contextSummary) {
-    ctx.messages.unshift(createContextSummaryMessage(contextSummary));
-  }
-
-  if (conv) {
-    ctx.usageStats = {
-      inputTokens: conv.totalInputTokens,
-      outputTokens: conv.totalOutputTokens,
-      estimatedCost: conv.totalEstimatedCost,
-    };
-  }
-
-  ctx.loadedHistoryTrustClass = trustClass;
-  ctx.loadedHistoryPersonalMemoryAllowed = personalMemoryAllowed;
-
-  log.info(
-    { conversationId: ctx.conversationId, count: ctx.messages.length },
-    "Loaded messages from DB",
-  );
-}
-
 // ── abort ─────────────────────────────────────────────────────────────
 
 export function abortConversation(
@@ -493,4 +242,11 @@ export function disposeConversation(ctx: DisposeContext): void {
   ctx.accumulatedSurfaceState.clear();
   ctx.lastSurfaceAction.clear();
   ctx.workspaceTopLevelContext = null;
+  // The compaction module owns the per-conversation ContextWindowManager, so
+  // teardown releases it directly. Moving this behind a compaction-plugin hook
+  // would let the module own disposal end-to-end, but the per-turn `stop` hook 
+  // would first require relocating the manager's only
+  // cross-turn state — `nonPersistedPrefixCount` — off the manager so a
+  // per-turn dispose/rebuild stays correct.
+  disposeContextWindowManager(ctx.conversationId);
 }

package/src/daemon/conversation-media-retry.ts

@@ -7,7 +7,7 @@
  */
 
 import { estimateContentBlockTokens } from "../context/token-estimator.js";
-import { getSummaryFromContextMessage } from "../context/window-manager.js";
+import { getSummaryFromContextMessage } from "../plugins/defaults/compaction/window-manager.js";
 import type { ContentBlock, Message } from "../providers/types.js";
 
 export interface StripMediaOptions {
@@ -173,15 +173,28 @@ export function estimateUnconditionalStubTokens(
     const msg = messages[msgIndex];
     for (const block of msg.content) {
       if (block.type === "image" && msgIndex !== latestUserIndex) {
-        stubTokens += estimateContentBlockTokens(imageBlockToStub(block), options);
+        stubTokens += estimateContentBlockTokens(
+          imageBlockToStub(block),
+          options,
+        );
       } else if (block.type === "file" && msgIndex !== latestUserIndex) {
-        stubTokens += estimateContentBlockTokens(fileBlockToStub(block), options);
-      } else if (block.type === "tool_result" && block.contentBlocks) { // guard:allow-tool-result-only — web_search_tool_result has no contentBlocks
+        stubTokens += estimateContentBlockTokens(
+          fileBlockToStub(block),
+          options,
+        );
+      } else if (block.type === "tool_result" && block.contentBlocks) {
+        // guard:allow-tool-result-only — web_search_tool_result has no contentBlocks
         for (const cb of block.contentBlocks) {
           if (cb.type === "image") {
-            stubTokens += estimateContentBlockTokens(imageBlockToStub(cb), options);
+            stubTokens += estimateContentBlockTokens(
+              imageBlockToStub(cb),
+              options,
+            );
           } else if (cb.type === "file") {
-            stubTokens += estimateContentBlockTokens(fileBlockToStub(cb), options);
+            stubTokens += estimateContentBlockTokens(
+              fileBlockToStub(cb),
+              options,
+            );
           }
         }
       }

package/src/daemon/conversation-messaging.ts

@@ -43,6 +43,7 @@ import {
 } from "../messaging/providers/slack/message-metadata.js";
 import type { SecretPrompter } from "../permissions/secret-prompter.js";
 import type { Message } from "../providers/types.js";
+import type { AuthContext } from "../runtime/auth/types.js";
 import { getLogger } from "../util/logger.js";
 import type { MessageQueue } from "./conversation-queue-manager.js";
 import type { SlackInboundMessageMetadata } from "./handlers/shared.js";
@@ -193,6 +194,9 @@ export interface MessagingConversationContext {
   currentRequestId?: string;
   readonly queue: MessageQueue;
   trustContext?: TrustContext;
+  authContext?: AuthContext;
+  currentTurnAuthContext?: AuthContext;
+  currentTurnSourceActorPrincipalId?: string;
   getTurnChannelContext(): TurnChannelContext | null;
   getTurnInterfaceContext(): TurnInterfaceContext | null;
 }
@@ -302,6 +306,10 @@ export interface EnqueueMessageOptions {
   displayContent?: string;
   transport?: ConversationTransportMetadata;
   clientMessageId?: string;
+  /** JWT-verified requester principal captured for queued host-proxy routing. */
+  sourceActorPrincipalId?: string;
+  /** Auth context snapshot captured for queued turn-scoped authorization. */
+  authContext?: AuthContext;
 }
 
 // ── enqueueMessage ───────────────────────────────────────────────────
@@ -322,7 +330,14 @@ export function enqueueMessage(
     displayContent,
     transport,
     clientMessageId,
+    authContext,
   } = options;
+  const queuedAuthContext =
+    authContext ?? ctx.currentTurnAuthContext ?? ctx.authContext;
+  const sourceActorPrincipalId =
+    options.sourceActorPrincipalId ??
+    ctx.currentTurnSourceActorPrincipalId ??
+    queuedAuthContext?.actorPrincipalId;
 
   if (!ctx.isProcessing()) {
     return { queued: false, requestId };
@@ -347,6 +362,8 @@ export function enqueueMessage(
     turnChannelContext,
     turnInterfaceContext,
     isInteractive,
+    sourceActorPrincipalId,
+    authContext: queuedAuthContext,
     transport,
     displayContent,
     sentAt: Date.now(),