diff --git a/proxy-server/src/conversation-manager.ts b/proxy-server/src/conversation-manager.ts
index 81c8e23..e883fb1 100644
--- a/proxy-server/src/conversation-manager.ts
+++ b/proxy-server/src/conversation-manager.ts
@@ -72,10 +72,21 @@ export class ConversationManager implements ToolStateProvider {
     if (isPrimary) {
       this.primaryId = id;
     } else {
-      state.session.onSessionEnd(() => {
+      const onSessionEnd = (): void => {
+        // The bridge sends tools/call right after the session goes idle.
+        // Removing the conversation while those calls are still pending would
+        // make them fail with "Conversation not found", so defer until they drain.
+        if (state.toolRouter.hasPending) {
+          this.logger.debug(
+            `Conversation ${id} session ended but tool calls pending, deferring removal`,
+          );
+          state.session.onSessionEnd(onSessionEnd);
+          return;
+        }
         this.logger.debug(`Conversation ${id} session ended, removing`);
         this.conversations.delete(id);
-      });
+      };
+      state.session.onSessionEnd(onSessionEnd);
     }
 
     this.logger.debug(
@@ -103,7 +114,11 @@ export class ConversationManager implements ToolStateProvider {
 
   private evictStale(): void {
     for (const [id, conv] of this.conversations) {
-      if (!conv.isPrimary && !conv.state.session.sessionActive) {
+      if (
+        !conv.isPrimary &&
+        !conv.state.session.sessionActive &&
+        !conv.state.toolRouter.hasPending
+      ) {
         conv.state.session.cleanup();
         this.conversations.delete(id);
         this.logger.debug(`Evicted stale conversation ${id}`);
diff --git a/proxy-server/src/tool-bridge/session-lifecycle.ts b/proxy-server/src/tool-bridge/session-lifecycle.ts
index d63f765..e68108a 100644
--- a/proxy-server/src/tool-bridge/session-lifecycle.ts
+++ b/proxy-server/src/tool-bridge/session-lifecycle.ts
@@ -48,9 +48,10 @@ export class SessionLifecycle {
   }
 
   private fireSessionEnd(): void {
-    if (this._onSessionEnd) {
-      this._onSessionEnd();
-      this._onSessionEnd = null;
-    }
+    // Clear before calling so the callback can register a new one without
+    // this method overwriting it.
+    const callback = this._onSessionEnd;
+    this._onSessionEnd = null;
+    if (callback) callback();
   }
 }
diff --git a/proxy-server/test/conversation-manager.test.ts b/proxy-server/test/conversation-manager.test.ts
index 46a5c75..a085083 100644
--- a/proxy-server/test/conversation-manager.test.ts
+++ b/proxy-server/test/conversation-manager.test.ts
@@ -1,4 +1,4 @@
-import { describe, it, expect } from "vitest";
+import { describe, it, expect, vi } from "vitest";
 import { ConversationManager } from "../src/conversation-manager.js";
 import { Logger } from "copilot-sdk-proxy";
 
@@ -189,6 +189,19 @@ describe("ConversationManager", () => {
       expect(manager.getState(conv.id)).toBe(conv.state);
       expect(manager.getPrimary()).toBe(conv);
     });
+
+    // An isolated conversation that goes idle right after emitting tool
+    // requests must stay alive because the bridge still has tools/call to deliver.
+    it("does NOT auto-remove non-primary conversation that has outstanding tool calls", () => {
+      const manager = createManager();
+      const conv = manager.create();
+      conv.state.session.markSessionActive();
+      conv.state.toolRouter.registerExpected("toolu_01abc", "XcodeRead");
+      conv.state.session.markSessionInactive();
+
+      expect(manager.size).toBe(1);
+      expect(manager.getState(conv.id)).toBe(conv.state);
+    });
   });
 
   describe("tool_use continuation after session goes inactive", () => {
@@ -400,6 +413,20 @@ describe("ConversationManager", () => {
       expect(manager.getPrimary()).toBe(primary);
     });
 
+    it("calls cleanup on evicted conversations", () => {
+      const manager = createManager();
+      const primary = manager.create({ isPrimary: true });
+      primary.session = { on: () => () => {} } as never;
+
+      const isolated = manager.create();
+      const cleanup = vi.spyOn(isolated.state.session, "cleanup");
+
+      manager.findForNewRequest();
+
+      expect(cleanup).toHaveBeenCalledOnce();
+      expect(manager.getState(isolated.id)).toBeUndefined();
+    });
+
     it("does NOT evict active non-primary conversations", () => {
       const manager = createManager();
       const primary = manager.create({ isPrimary: true });
@@ -414,7 +441,9 @@ describe("ConversationManager", () => {
       expect(manager.size).toBe(3);
     });
 
-    it("calls cleanup on evicted conversations", async () => {
+    // A new request must not evict an isolated conversation that still has a
+    // tool call in flight, or the bridge loses it before the result comes back.
+    it("does NOT evict conversations with in-flight tool calls", async () => {
       const manager = createManager();
       const primary = manager.create({ isPrimary: true });
       primary.session = { on: () => () => {} } as never;
@@ -426,7 +455,12 @@ describe("ConversationManager", () => {
       });
 
       manager.findForNewRequest();
-      await expect(resultPromise).rejects.toThrow();
+
+      expect(manager.getState(isolated.id)).toBe(isolated.state);
+      expect(isolated.state.toolRouter.resolveToolCall("call-1", "ok")).toBe(
+        true,
+      );
+      await expect(resultPromise).resolves.toBe("ok");
     });
   });
 });