fix: avoid cancelling in-flight tool approvals

Co-Authored-By: Paperclip <noreply@paperclip.ing>

server/src/__tests__/tool-access-service.test.ts

@@ -4148,7 +4148,7 @@ describeEmbeddedPostgres("tool access service", () => {
       schemaHash: "s1",
     }).returning();
     const canonicalArguments = canonicalToolArguments({ key: "alpha", value: "one" });
-    const invocationValues = [1, 2, 3].map(() => ({
+    const invocationValues = [1, 2, 3, 4].map(() => ({
       companyId: company.id,
       applicationId: application.id,
       connectionId: connection.id,
@@ -4160,7 +4160,7 @@ describeEmbeddedPostgres("tool access service", () => {
       approvalState: "pending" as const,
       status: "awaiting_approval" as const,
     }));
-    const [validInvocation, missingSignatureInvocation, oldSecretInvocation] =
+    const [validInvocation, missingSignatureInvocation, oldSecretInvocation, inFlightInvocation] =
       await db.insert(toolInvocations).values(invocationValues).returning();
     const validSignedArguments = signToolArguments({
       invocationId: validInvocation.id,
@@ -4174,7 +4174,7 @@ describeEmbeddedPostgres("tool access service", () => {
       canonicalArguments,
       signingSecret: "old-secret",
     });
-    const [validRequest, missingSignatureRequest, oldSecretRequest] = await db.insert(toolActionRequests).values([
+    const [validRequest, missingSignatureRequest, oldSecretRequest, inFlightRequest] = await db.insert(toolActionRequests).values([
       {
         companyId: company.id,
         invocationId: validInvocation.id,
@@ -4190,6 +4190,7 @@ describeEmbeddedPostgres("tool access service", () => {
         canonicalArgumentsHash: "args-hash",
         canonicalArgumentsSummary: { summary: canonicalArguments, sha256: "args-hash", sizeBytes: canonicalArguments.length },
         signedArguments: null,
+        createdAt: new Date(Date.now() - 60_000),
       },
       {
         companyId: company.id,
@@ -4199,6 +4200,14 @@ describeEmbeddedPostgres("tool access service", () => {
         canonicalArgumentsSummary: { summary: canonicalArguments, sha256: "args-hash", sizeBytes: canonicalArguments.length },
         signedArguments: oldSecretSignedArguments,
       },
+      {
+        companyId: company.id,
+        invocationId: inFlightInvocation.id,
+        status: "pending",
+        canonicalArgumentsHash: "args-hash",
+        canonicalArgumentsSummary: { summary: canonicalArguments, sha256: "args-hash", sizeBytes: canonicalArguments.length },
+        signedArguments: null,
+      },
     ]).returning();
 
     const list = await toolAccessService(db).listActionRequests(company.id, "pending");
@@ -4209,6 +4218,7 @@ describeEmbeddedPostgres("tool access service", () => {
     expect(statusById.get(validRequest.id)).toBe("pending");
     expect(statusById.get(missingSignatureRequest.id)).toBe("cancelled");
     expect(statusById.get(oldSecretRequest.id)).toBe("cancelled");
+    expect(statusById.get(inFlightRequest.id)).toBe("pending");
   });
 
   it("tracks new profile tools, reviews mixed allow/block decisions, and clears pending counts", async () => {

server/src/services/tool-access.ts

@@ -147,6 +147,7 @@ type OAuthProviderEndpoints = {
 };
 
 const oauthRegistrationFlights = new Map<string, Promise<unknown>>();
+const PENDING_ACTION_REQUEST_SIGNING_GRACE_MS = 5_000;
 
 async function oauthSingleFlight<T>(
   flights: Map<string, Promise<unknown>>,
@@ -6749,10 +6750,19 @@ export function toolAccessService(db: Db, options: ToolAccessServiceOptions = {}
       const invocationById = new Map(invocations.map((invocation) => [invocation.id, invocation]));
       let visibleRequests = requests;
       if (status === "pending") {
+        const hiddenInFlightRequestIds = new Set<string>();
+        const signingGraceDeadline = now().getTime() - PENDING_ACTION_REQUEST_SIGNING_GRACE_MS;
         const invalidRequestIds = requests
           .filter((request) => {
             const invocation = invocationById.get(request.invocationId);
             if (!invocation) return true;
+            if (!request.signedArguments && request.createdAt.getTime() > signingGraceDeadline) {
+              // recordInvocation inserts the pending row before executeTestCall adds
+              // its signed payload. A concurrent review-queue poll must not cancel
+              // that short-lived intermediate state.
+              hiddenInFlightRequestIds.add(request.id);
+              return false;
+            }
             try {
               return !readSignedToolArgumentsPayload({
                 signedArguments: request.signedArguments,
@@ -6776,6 +6786,9 @@ export function toolAccessService(db: Db, options: ToolAccessServiceOptions = {}
           const invalidIds = new Set(invalidRequestIds);
           visibleRequests = requests.filter((request) => !invalidIds.has(request.id));
         }
+        if (hiddenInFlightRequestIds.size > 0) {
+          visibleRequests = visibleRequests.filter((request) => !hiddenInFlightRequestIds.has(request.id));
+        }
       }
       if (visibleRequests.length === 0) return [];