🤖 Add truncation: auto to OpenAI Responses API

docs/context-management.md

@@ -101,3 +101,18 @@ Remove oldest 50% of messages.
 - About as fast as `/clear`
 - `/truncate 100` is equivalent to `/clear`
 - **Irreversible** - messages are permanently removed
+
+### OpenAI Responses API Limitation
+
+⚠️ **`/truncate` does not work with OpenAI models** due to the Responses API architecture:
+
+- OpenAI's Responses API stores conversation state server-side
+- Manual message deletion via `/truncate` doesn't affect the server-side state
+- Instead, OpenAI models use **automatic truncation** (`truncation: "auto"`)
+- When context exceeds the limit, the API automatically drops messages from the middle of the conversation
+
+**Workarounds for OpenAI:**
+
+- Use `/clear` to start a fresh conversation
+- Use `/compact` to intelligently summarize and reduce context
+- Rely on automatic truncation (enabled by default)

src/services/aiService.ts

@@ -174,7 +174,10 @@ export class AIService extends EventEmitter {
    * constructor, ensuring automatic parity with Vercel AI SDK - any configuration options
    * supported by the provider will work without modification.
    */
-  private createModel(modelString: string): Result<LanguageModel, SendMessageError> {
+  private createModel(
+    modelString: string,
+    options?: { disableAutoTruncation?: boolean }
+  ): Result<LanguageModel, SendMessageError> {
     try {
       // Parse model string (format: "provider:model-id")
       const [providerName, modelId] = modelString.split(":");
@@ -220,10 +223,81 @@ export class AIService extends EventEmitter {
             ? (providerConfig.fetch as typeof fetch)
             : defaultFetchWithUnlimitedTimeout;
 
+        // Wrap fetch to force truncation: "auto" for OpenAI Responses API calls.
+        // This is a temporary override until @ai-sdk/openai supports passing
+        // truncation via providerOptions. Safe because it only targets the
+        // OpenAI Responses endpoint and leaves other providers untouched.
+        // Can be disabled via options for testing purposes.
+        const disableAutoTruncation = options?.disableAutoTruncation ?? false;
+        const fetchWithOpenAITruncation = Object.assign(
+          async (
+            input: Parameters<typeof fetch>[0],
+            init?: Parameters<typeof fetch>[1]
+          ): Promise<Response> => {
+            try {
+              const urlString = (() => {
+                if (typeof input === "string") {
+                  return input;
+                }
+                if (input instanceof URL) {
+                  return input.toString();
+                }
+                if (typeof input === "object" && input !== null && "url" in input) {
+                  const possibleUrl = (input as { url?: unknown }).url;
+                  if (typeof possibleUrl === "string") {
+                    return possibleUrl;
+                  }
+                }
+                return "";
+              })();
+
+              const method = (init?.method ?? "GET").toUpperCase();
+              const isOpenAIResponses = /\/v1\/responses(\?|$)/.test(urlString);
+
+              const body = init?.body;
+              if (
+                !disableAutoTruncation &&
+                isOpenAIResponses &&
+                method === "POST" &&
+                typeof body === "string"
+              ) {
+                // Clone headers to avoid mutating caller-provided objects
+                const headers = new Headers(init?.headers);
+                // Remove content-length if present, since body will change
+                headers.delete("content-length");
+
+                try {
+                  const json = JSON.parse(body) as Record<string, unknown>;
+                  // Only set if not already present
+                  if (json.truncation === undefined) {
+                    json.truncation = "auto";
+                  }
+                  const newBody = JSON.stringify(json);
+                  const newInit: RequestInit = { ...init, headers, body: newBody };
+                  return fetchToUse(input, newInit);
+                } catch {
+                  // If body isn't JSON, fall through to normal fetch
+                  return fetchToUse(input, init);
+                }
+              }
+
+              // Default passthrough
+              return fetchToUse(input, init);
+            } catch {
+              // On any unexpected error, fall back to original fetch
+              return fetchToUse(input, init);
+            }
+          },
+          "preconnect" in fetchToUse &&
+            typeof (fetchToUse as typeof fetch).preconnect === "function"
+            ? { preconnect: (fetchToUse as typeof fetch).preconnect.bind(fetchToUse) }
+            : {}
+        );
+
         const provider = createOpenAI({
           ...providerConfig,
           // eslint-disable-next-line @typescript-eslint/no-unsafe-assignment, @typescript-eslint/no-explicit-any
-          fetch: fetchToUse as any,
+          fetch: fetchWithOpenAITruncation as any,
         });
         // Use Responses API for persistence and built-in tools
         const baseModel = provider.responses(modelId);
@@ -267,7 +341,8 @@ export class AIService extends EventEmitter {
     toolPolicy?: ToolPolicy,
     abortSignal?: AbortSignal,
     additionalSystemInstructions?: string,
-    maxOutputTokens?: number
+    maxOutputTokens?: number,
+    disableAutoTruncation?: boolean
   ): Promise<Result<void, SendMessageError>> {
     try {
       // DEBUG: Log streamMessage call
@@ -281,7 +356,7 @@ export class AIService extends EventEmitter {
       await this.partialService.commitToHistory(workspaceId);
 
       // Create model instance with early API key validation
-      const modelResult = this.createModel(modelString);
+      const modelResult = this.createModel(modelString, { disableAutoTruncation });
       if (!modelResult.success) {
         return Err(modelResult.error);
       }

src/services/ipcMain.ts

@@ -435,6 +435,7 @@ export class IpcMain {
           toolPolicy,
           additionalSystemInstructions,
           maxOutputTokens,
+          disableAutoTruncation,
         } = options ?? {};
         log.debug("sendMessage handler: Received", {
           workspaceId,
@@ -445,6 +446,7 @@ export class IpcMain {
           toolPolicy,
           additionalSystemInstructions,
           maxOutputTokens,
+          disableAutoTruncation,
         });
         try {
           // Early exit: empty message = either interrupt (if streaming) or invalid input
@@ -539,6 +541,7 @@ export class IpcMain {
             toolPolicy,
             additionalSystemInstructions,
             maxOutputTokens,
+            disableAutoTruncation,
           });
           const streamResult = await this.aiService.streamMessage(
             historyResult.data,
@@ -548,7 +551,8 @@ export class IpcMain {
             toolPolicy,
             undefined,
             additionalSystemInstructions,
-            maxOutputTokens
+            maxOutputTokens,
+            disableAutoTruncation
           );
           log.debug("sendMessage handler: Stream completed");
           return streamResult;

src/types/ipc.ts

@@ -131,6 +131,7 @@ export interface SendMessageOptions {
   toolPolicy?: ToolPolicy;
   additionalSystemInstructions?: string;
   maxOutputTokens?: number;
+  disableAutoTruncation?: boolean; // For testing truncation behavior
 }
 
 // API method signatures (shared between main and preload)

src/utils/ai/providerOptions.ts

@@ -11,12 +11,29 @@ import { ANTHROPIC_THINKING_BUDGETS, OPENAI_REASONING_EFFORT } from "@/types/thi
 import { log } from "@/services/log";
 import type { CmuxMessage } from "@/types/message";
 
+/**
+ * Extended OpenAI Responses provider options to include truncation
+ *
+ * NOTE: The SDK types don't yet include this parameter, but it's supported by the OpenAI API.
+ * However, the @ai-sdk/openai v2.0.40 implementation does NOT pass truncation from provider
+ * options - it only sets it based on modelConfig.requiredAutoTruncation.
+ *
+ * This type extension is prepared for a future SDK update that will properly map the
+ * truncation parameter from provider options to the API request.
+ *
+ * Current behavior: OpenAI models will NOT use truncation: "auto" until the SDK is updated.
+ * Workaround: Use /clear or /compact commands to manage conversation history.
+ */
+type ExtendedOpenAIResponsesProviderOptions = OpenAIResponsesProviderOptions & {
+  truncation?: "auto" | "disabled";
+};
+
 /**
  * Provider-specific options structure for AI SDK
  */
 type ProviderOptions =
   | { anthropic: AnthropicProviderOptions }
-  | { openai: OpenAIResponsesProviderOptions }
+  | { openai: ExtendedOpenAIResponsesProviderOptions }
   | Record<string, never>; // Empty object for unsupported providers
 
 /**
@@ -111,6 +128,7 @@ export function buildProviderOptions(
         parallelToolCalls: true, // Always enable concurrent tool execution
         // TODO: allow this to be configured
         serviceTier: "priority", // Always use priority tier for best performance
+        truncation: "auto", // Automatically truncate conversation to fit context window
         // Conditionally add reasoning configuration
         ...(reasoningEffort && {
           reasoningEffort,

tests/ipcMain/sendMessage.test.ts

@@ -698,12 +698,14 @@ describeIntegration("IpcMain sendMessage integration tests", () => {
 
           // Now try to send a new message - should trigger token limit error
           // due to accumulated history
+          // Disable auto-truncation to force context error
           const result = await sendMessageWithModel(
             env.mockIpcRenderer,
             workspaceId,
             "What is the weather?",
             provider,
-            model
+            model,
+            { disableAutoTruncation: true }
           );
 
           // IPC call itself should succeed (errors come through stream events)
@@ -956,4 +958,104 @@ describeIntegration("IpcMain sendMessage integration tests", () => {
       15000
     );
   });
+
+  // OpenAI auto truncation integration test
+  // This test verifies that the truncation: "auto" parameter works correctly
+  // by first forcing a context overflow error, then verifying recovery with auto-truncation
+  describeIntegration("OpenAI auto truncation integration", () => {
+    const provider = "openai";
+    const model = "gpt-4o-mini";
+
+    test.concurrent(
+      "respects disableAutoTruncation flag",
+      async () => {
+        const { env, workspaceId, cleanup } = await setupWorkspace(provider);
+
+        try {
+          // Phase 1: Build up large conversation history to exceed context limit
+          // HACK: Use HistoryService directly to populate history without API calls.
+          // This is a test-only shortcut. Real application code should NEVER bypass IPC.
+          const historyService = new HistoryService(env.config);
+
+          // gpt-4o-mini has ~128k token context window
+          // Create ~50k chars per message (~12.5k tokens)
+          const messageSize = 50_000;
+          const largeText = "A".repeat(messageSize);
+
+          // Need ~150k tokens to exceed 128k context limit
+          // 12 messages × 12.5k tokens = 150k tokens
+          const messageCount = 12;
+
+          // Build conversation history with alternating user/assistant messages
+          for (let i = 0; i < messageCount; i++) {
+            const isUser = i % 2 === 0;
+            const role = isUser ? "user" : "assistant";
+            const message = createCmuxMessage(`history-msg-${i}`, role, largeText, {});
+
+            const result = await historyService.appendToHistory(workspaceId, message);
+            expect(result.success).toBe(true);
+          }
+
+          // Now send a new message with auto-truncation disabled - should trigger error
+          const result = await sendMessageWithModel(
+            env.mockIpcRenderer,
+            workspaceId,
+            "This should trigger a context error",
+            provider,
+            model,
+            { disableAutoTruncation: true }
+          );
+
+          // IPC call itself should succeed (errors come through stream events)
+          expect(result.success).toBe(true);
+
+          // Wait for either stream-end or stream-error
+          const collector = createEventCollector(env.sentEvents, workspaceId);
+          await Promise.race([
+            collector.waitForEvent("stream-end", 10000),
+            collector.waitForEvent("stream-error", 10000),
+          ]);
+
+          // Should have received error event with context exceeded error
+          expect(collector.hasError()).toBe(true);
+
+          // Check that error message contains context-related keywords
+          const errorEvents = collector
+            .getEvents()
+            .filter((e) => "type" in e && e.type === "stream-error");
+          expect(errorEvents.length).toBeGreaterThan(0);
+
+          const errorEvent = errorEvents[0];
+          if (errorEvent && "error" in errorEvent) {
+            const errorStr = String(errorEvent.error).toLowerCase();
+            expect(
+              errorStr.includes("context") ||
+                errorStr.includes("length") ||
+                errorStr.includes("exceed") ||
+                errorStr.includes("token")
+            ).toBe(true);
+          }
+
+          // Phase 2: Send message with auto-truncation enabled (should succeed)
+          env.sentEvents.length = 0;
+          const successResult = await sendMessageWithModel(
+            env.mockIpcRenderer,
+            workspaceId,
+            "This should succeed with auto-truncation",
+            provider,
+            model
+            // disableAutoTruncation defaults to false (auto-truncation enabled)
+          );
+
+          expect(successResult.success).toBe(true);
+          const successCollector = createEventCollector(env.sentEvents, workspaceId);
+          await successCollector.waitForEvent("stream-end", 30000);
+          assertStreamSuccess(successCollector);
+        } finally {
+          await cleanup();
+        }
+      },
+      60000 // 1 minute timeout (much faster since we don't make many API calls)
+    );
+  });
 });