@animalabs/membrane 0.5.72 → 0.5.73

package/dist/yielding-stream.js.map

@@ -1 +1 @@
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package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@animalabs/membrane",
-  "version": "0.5.72",
+  "version": "0.5.73",
   "description": "LLM middleware - a selective boundary that transforms what passes through",
   "repository": {
     "type": "git",

package/src/cache-thinking-guard.test.ts

@@ -0,0 +1,34 @@
+/**
+ * Regression: a cache breakpoint must never land on a thinking block.
+ *
+ * The API rejects `cache_control` on thinking / redacted_thinking with
+ * 400 "thinking.cache_control: Extra inputs are not permitted". The rule was
+ * fixed in NativeFormatter (2026-07-01) but NOT in Membrane.buildNativeToolRequest
+ * — the live Connectome path — so the 400 returned on 2026-07-14 the moment a
+ * breakpoint landed on a thinking-terminated turn. One shared helper now.
+ */
+import { describe, it, expect } from 'vitest';
+import { lastCacheableBlockIndex } from './formatters/native.js';
+
+describe('lastCacheableBlockIndex', () => {
+  it('steps back past a trailing thinking block', () => {
+    expect(lastCacheableBlockIndex([
+      { type: 'text', text: 'hi' },
+      { type: 'thinking', thinking: '', signature: 'sig' },
+    ])).toBe(0);
+  });
+
+  it('skips the breakpoint entirely for a thinking-only message', () => {
+    expect(lastCacheableBlockIndex([
+      { type: 'thinking', thinking: '', signature: 'sig' },
+      { type: 'redacted_thinking', data: 'x' },
+    ])).toBe(-1);
+  });
+
+  it('uses the last block when it is cacheable', () => {
+    expect(lastCacheableBlockIndex([
+      { type: 'thinking', thinking: '', signature: 'sig' },
+      { type: 'tool_use', name: 't', input: {} },
+    ])).toBe(1);
+  });
+});

package/src/formatters/native.ts

@@ -35,7 +35,7 @@ import { isAcceptedImageMediaType, strippedImagePlaceholder } from '../utils/ima
  *  rejects cache_control on thinking / redacted_thinking blocks, so a cache
  *  breakpoint must attach to the last NON-thinking block. Returns -1 when the
  *  message has only thinking blocks (the breakpoint is then skipped). */
-function lastCacheableBlockIndex(blocks: Array<Record<string, unknown>>): number {
+export function lastCacheableBlockIndex(blocks: Array<Record<string, unknown>>): number {
   for (let k = blocks.length - 1; k >= 0; k--) {
     const t = blocks[k]?.type as string | undefined;
     if (t !== 'thinking' && t !== 'redacted_thinking') return k;

package/src/membrane.ts

@@ -26,6 +26,7 @@ import type {
   ToolMode,
   ToolDefinition,
 } from './types/index.js';
+import { lastCacheableBlockIndex } from './formatters/native.js';
 import {
   DEFAULT_RETRY_CONFIG,
   MembraneError,
@@ -1087,10 +1088,24 @@ export class Membrane {
         }
       }
 
-      // Apply cache_control to last block of messages with cacheBreakpoint
+      // Apply cache_control to the last CACHEABLE block of messages with a
+      // cacheBreakpoint. The API rejects cache_control on thinking /
+      // redacted_thinking blocks (400 "thinking.cache_control: Extra inputs
+      // are not permitted"), so a breakpoint landing on a thinking-terminated
+      // message must step back to the last non-thinking block — and is skipped
+      // entirely when the message is thinking-only.
+      //
+      // 2026-07-14: this is the THIRD request builder to need the rule. The
+      // 2026-07-01 fix hardened NativeFormatter's two sites but not this one,
+      // which is the live Connectome path (native tools + thinking) — so the
+      // 400 came back the moment a breakpoint landed on a thinking-only turn.
+      // The rule now lives in ONE exported helper that every builder calls.
       if (msg.cacheBreakpoint && cacheControl && content.length > 0) {
-        content[content.length - 1].cache_control = cacheControl;
-        messageBreakpoints++;
+        const bpIdx = lastCacheableBlockIndex(content as Array<Record<string, unknown>>);
+        if (bpIdx >= 0) {
+          content[bpIdx].cache_control = cacheControl;
+          messageBreakpoints++;
+        }
       }
 
       providerMessages.push({ role, content });
@@ -2001,6 +2016,8 @@ export class Membrane {
     const formatter = this.formatter;
     const parser = formatter.createStreamParser();
     let toolDepth = 0;
+    // Once-per-stream latch for the injectedMessages-unsupported warning.
+    let warnedInjectionUnsupported = false;
     let totalUsage: DetailedUsage = { inputTokens: 0, outputTokens: 0 };
     const pricing = this.resolvePricing(request.config.model);
     const contentBlocks: ContentBlock[] = [];
@@ -2224,7 +2241,21 @@ export class Membrane {
               context,
             };
 
-            const results = await stream.requestToolExecution(toolCallsEvent);
+            const { results, injectedMessages } = await stream.requestToolExecution(toolCallsEvent);
+
+            // Mid-turn injected messages are not supported on the XML prefill
+            // path: the continuation is an assistant prefill over an XML
+            // transcript, not a message array, so there is no user envelope
+            // to append to. Warn (once per stream — long turns have many
+            // rounds) rather than drop silently; the messages remain in the
+            // caller's context window and reach the model on the next turn.
+            if (injectedMessages && injectedMessages.length > 0 && !warnedInjectionUnsupported) {
+              warnedInjectionUnsupported = true;
+              console.warn(
+                `[membrane] provideToolResults injectedMessages ignored: XML tool mode ` +
+                `does not support mid-turn injection (delivered next turn instead)`
+              );
+            }
 
             // Track the tool results
             executedToolResults.push(...results);
@@ -2647,7 +2678,7 @@ export class Membrane {
             context,
           };
 
-          const results = await stream.requestToolExecution(toolCallsEvent);
+          const { results, injectedMessages } = await stream.requestToolExecution(toolCallsEvent);
 
           // Track tool results
           executedToolResults.push(...results);
@@ -2665,13 +2696,14 @@ export class Membrane {
           // Add messages for next iteration — use the request's participant names
           const assistantName = request.assistantParticipant
             ?? this.config.assistantParticipant ?? 'Claude';
+          const userName = assistantName === 'Claude' ? 'User' : 'user';
           messages.push({
             participant: assistantName,
             content: responseBlocks,
           });
 
           messages.push({
-            participant: assistantName === 'Claude' ? 'User' : 'user',
+            participant: userName,
             content: results.map(r => ({
               type: 'tool_result' as const,
               toolUseId: r.toolUseId,
@@ -2680,6 +2712,23 @@ export class Membrane {
             })),
           });
 
+          // Mid-turn injection: messages that arrived while this round's
+          // tools were executing, appended AFTER the tool_result envelope so
+          // the next inference round sees them. Placed here (not co-mingled
+          // with the results) so provider conversions that special-case
+          // tool_result envelopes (e.g. ChatCompletions role:'tool') carry
+          // them as ordinary user messages. Signed-thinking adjacency is
+          // unaffected: the assistant turn above is round-tripped verbatim.
+          if (injectedMessages) {
+            for (const injected of injectedMessages) {
+              messages.push({
+                participant: injected.participant ?? userName,
+                content: injected.content,
+                ...(injected.metadata ? { metadata: injected.metadata } : {}),
+              });
+            }
+          }
+
           toolDepth++;
           continue;
         }

package/src/providers/openai-compatible.ts

@@ -409,8 +409,25 @@ export class OpenAICompatibleAdapter implements ProviderAdapter {
           }
         }
 
-        // If we have tool results, return them (possibly multiple)
+        // If we have tool results, emit them (possibly multiple) as
+        // role:'tool' messages — plus a FOLLOWING user message for any other
+        // content sharing the envelope (e.g. a mid-turn injected user message
+        // that mergeConsecutiveRoles folded into the tool_result envelope),
+        // instead of silently dropping it. Mirrors openai.ts / openrouter.ts.
         if (toolResults.length > 0) {
+          const hasImagesInterloper = contentParts.some(p => p.type === 'image_url');
+          const interloperText = hasImagesInterloper
+            ? ''
+            : contentParts.filter(p => p.type === 'text').map(p => p.text!).join('\n');
+          if (hasImagesInterloper || interloperText) {
+            return [
+              ...toolResults,
+              {
+                role: 'user' as const,
+                content: hasImagesInterloper ? contentParts : interloperText,
+              },
+            ];
+          }
           return toolResults;
         }
 

package/src/providers/openai.ts

@@ -472,8 +472,27 @@ export class OpenAIAdapter implements ProviderAdapter {
           }
         }
 
-        // If we have tool results, return them (possibly multiple)
+        // If we have tool results, emit them (possibly multiple) as
+        // role:'tool' messages. Any OTHER content sharing the envelope
+        // (e.g. a mid-turn user message injected alongside tool_results —
+        // mergeConsecutiveRoles folds the separately-pushed injected user
+        // message INTO the tool_result envelope) is emitted as a FOLLOWING
+        // user message rather than dropped — this used to silently swallow
+        // such text. Same fix in openrouter.ts / openai-compatible.ts.
         if (toolResults.length > 0) {
+          const hasImagesInterloper = contentParts.some(p => p.type === 'image_url');
+          const interloperText = hasImagesInterloper
+            ? '' // unused: array form carries the parts
+            : contentParts.filter(p => p.type === 'text').map(p => p.text!).join('\n');
+          if (hasImagesInterloper || interloperText) {
+            return [
+              ...toolResults,
+              {
+                role: 'user' as const,
+                content: hasImagesInterloper ? contentParts : interloperText,
+              },
+            ];
+          }
           return toolResults;
         }
 

package/src/providers/openrouter.ts

@@ -514,8 +514,25 @@ export class OpenRouterAdapter implements ProviderAdapter {
           }
         }
 
-        // If we have tool results, return them (possibly multiple)
+        // If we have tool results, emit them (possibly multiple) as
+        // role:'tool' messages — plus a FOLLOWING user message for any other
+        // content sharing the envelope (e.g. a mid-turn injected user message
+        // that mergeConsecutiveRoles folded into the tool_result envelope),
+        // instead of silently dropping it. Mirrors openai.ts / openai-compatible.ts.
         if (toolResults.length > 0) {
+          const interloperText = textParts.join('\n');
+          if (contentBlocks.length > 0) {
+            return [
+              ...toolResults,
+              { role: 'user' as const, content: contentBlocks },
+            ];
+          }
+          if (interloperText) {
+            return [
+              ...toolResults,
+              { role: 'user' as const, content: interloperText },
+            ];
+          }
           return toolResults;
         }
 

package/src/types/index.ts

@@ -132,6 +132,8 @@ export type {
   StreamEvent,
   YieldingStream,
   YieldingStreamOptions,
+  InjectedMessage,
+  ProvideToolResultsOptions,
 } from './yielding-stream.js';
 
 export {

package/src/types/yielding-stream.ts

@@ -9,6 +9,7 @@
  */
 
 import type { ContentBlock } from './content.js';
+import type { NormalizedMessage } from './message.js';
 import type { ToolCall, ToolResult, ToolContext } from './tools.js';
 import type { DetailedUsage, NormalizedResponse, StopReason } from './response.js';
 import type { ChunkMeta, BlockEvent } from './streaming.js';
@@ -122,15 +123,63 @@ export type StreamEvent =
  * }
  * ```
  */
+/**
+ * A user-side message injected into the conversation between tool rounds.
+ *
+ * This is how a consumer lets the model see events that arrived while the
+ * turn was in flight (e.g. a chat reply landing mid-way through a long
+ * tool-using turn): pass it alongside the tool results and the next
+ * inference round's request includes it as a user message AFTER the
+ * tool_result envelope.
+ *
+ * Placement guarantee: injected messages always land after the round's
+ * tool_results (the wire normalizer additionally enforces results-first
+ * ordering inside a merged envelope), so they never break the
+ * tool_use → tool_result adjacency or signed-thinking constraints.
+ *
+ * Shape: NormalizedMessage minus cacheBreakpoint (breakpoints are the
+ * request compiler's concern), with `participant` optional — it defaults to
+ * the generic user participant. Non-assistant participants get the standard
+ * "Name: " text prefix when rendered to the provider. Content must be
+ * user-side blocks only (text/image); tool blocks are stripped with a
+ * warning. NOTE: a participant equal to the request's assistantParticipant
+ * would render as an ASSISTANT turn (a prefill) — callers should not inject
+ * messages named as the assistant.
+ */
+export type InjectedMessage =
+  Omit<NormalizedMessage, 'participant' | 'cacheBreakpoint'> & {
+    participant?: string;
+  };
+
+/**
+ * Options for provideToolResults().
+ */
+export interface ProvideToolResultsOptions {
+  /**
+   * Messages that arrived while the turn was in flight, to be appended to
+   * the conversation after this round's tool_result envelope so the NEXT
+   * inference round sees them.
+   *
+   * Supported in native tool mode (Anthropic Messages, OpenAI Responses,
+   * OpenRouter). The XML prefill path currently ignores these (the
+   * continuation is an assistant prefill, not a message array) — callers
+   * on XML-mode models should deliver mid-turn events on the next turn
+   * instead.
+   */
+  injectedMessages?: InjectedMessage[];
+}
+
 export interface YieldingStream extends AsyncIterable<StreamEvent> {
   /**
    * Provide tool results after receiving a 'tool-calls' event.
    * The stream will resume and continue generating.
    *
    * @param results - Results for the tool calls (must match call IDs)
+   * @param options - Optionally inject mid-turn user messages into the
+   *   next round (see ProvideToolResultsOptions.injectedMessages)
    * @throws Error if called when not waiting for tool results
    */
-  provideToolResults(results: ToolResult[]): void;
+  provideToolResults(results: ToolResult[], options?: ProvideToolResultsOptions): void;
 
   /**
    * Cancel the stream. Any in-flight requests will be aborted.

package/src/yielding-stream.ts

@@ -10,9 +10,21 @@ import type {
   YieldingStream,
   YieldingStreamOptions,
   ToolCallsEvent,
+  InjectedMessage,
+  ProvideToolResultsOptions,
 } from './types/yielding-stream.js';
 import type { ToolResult } from './types/tools.js';
 
+/**
+ * Payload handed from provideToolResults() to the inference loop awaiting
+ * requestToolExecution(): the round's tool results plus any mid-turn
+ * messages the consumer wants the next inference round to see.
+ */
+export interface ToolResultsPayload {
+  results: ToolResult[];
+  injectedMessages?: InjectedMessage[];
+}
+
 // ============================================================================
 // Internal State Types
 // ============================================================================
@@ -25,7 +37,7 @@ type StreamState =
   | { status: 'error'; error: Error };
 
 interface PendingToolResults {
-  resolve: (results: ToolResult[]) => void;
+  resolve: (payload: ToolResultsPayload) => void;
   reject: (error: Error) => void;
 }
 
@@ -98,7 +110,7 @@ export class YieldingStreamImpl implements YieldingStream {
     return this.abortController.signal;
   }
 
-  provideToolResults(results: ToolResult[]): void {
+  provideToolResults(results: ToolResult[], options?: ProvideToolResultsOptions): void {
     if (this.state.status !== 'waiting_for_tools') {
       throw new Error(
         `Cannot provide tool results: stream is not waiting for tools (status: ${this.state.status})`
@@ -119,8 +131,32 @@ export class YieldingStreamImpl implements YieldingStream {
       }
     }
 
+    // Injected messages must be user-side content only — tool blocks here
+    // would corrupt the tool-cycle structure the normalizer guarantees.
+    // Offending BLOCKS are stripped (loudly) rather than thrown on: a throw
+    // at this point would leave the stream parked in waiting_for_tools with
+    // an unresolvable promise — wedging the caller's whole turn over a
+    // notification is far worse than delivering it without its tool blocks.
+    const injectedMessages = options?.injectedMessages
+      ?.map((m) => {
+        const clean = m.content.filter(
+          (block) => block.type !== 'tool_use' && block.type !== 'tool_result'
+        );
+        if (clean.length !== m.content.length) {
+          console.warn(
+            `[membrane] provideToolResults: stripped ${m.content.length - clean.length} ` +
+            `tool block(s) from an injected mid-turn message (user-side content only)`
+          );
+        }
+        return { ...m, content: clean };
+      })
+      .filter((m) => m.content.length > 0);
+
     // Resolve the promise and transition state
-    this.pendingToolResults.resolve(results);
+    this.pendingToolResults.resolve({
+      results,
+      ...(injectedMessages && injectedMessages.length > 0 ? { injectedMessages } : {}),
+    });
     this.pendingToolResults = null;
     this.state = { status: 'streaming' };
     this._toolDepth++;
@@ -198,7 +234,7 @@ export class YieldingStreamImpl implements YieldingStream {
    * Request tool execution and wait for results.
    * Called by the inference loop when tool calls are detected.
    */
-  async requestToolExecution(event: ToolCallsEvent): Promise<ToolResult[]> {
+  async requestToolExecution(event: ToolCallsEvent): Promise<ToolResultsPayload> {
     // Emit the tool calls event
     this.emit(event);
 
@@ -209,7 +245,7 @@ export class YieldingStreamImpl implements YieldingStream {
     };
 
     // Create a promise that will be resolved by provideToolResults()
-    return new Promise<ToolResult[]>((resolve, reject) => {
+    return new Promise<ToolResultsPayload>((resolve, reject) => {
       this.pendingToolResults = { resolve, reject };
     });
   }