diff --git a/dev/local/env-sync/plan.ts b/dev/local/env-sync/plan.ts
index d9ec80f9f8..bb84d83b68 100644
--- a/dev/local/env-sync/plan.ts
+++ b/dev/local/env-sync/plan.ts
@@ -219,7 +219,7 @@ function computePlan(repoRoot: string, serviceFilter?: Set<string>): EnvSyncPlan
     const serviceUsesLanIp = dirUsesLanIp.get(workerDir) ?? false;
 
     const resolvedVars = new Map<string, string>();
-    const missingValues: string[] = [];
+    const unresolvedKeys: string[] = [];
 
     for (const entry of entries) {
       const { value, resolved } = resolveAnnotatedValue(
@@ -230,7 +230,7 @@ function computePlan(repoRoot: string, serviceFilter?: Set<string>): EnvSyncPlan
         serviceUsesLanIp
       );
       resolvedVars.set(entry.key, value);
-      if (!resolved) missingValues.push(entry.key);
+      if (!resolved) unresolvedKeys.push(entry.key);
     }
 
     allResolvedEntries.set(workerDir, { vars: resolvedVars, entries });
@@ -246,17 +246,24 @@ function computePlan(repoRoot: string, serviceFilter?: Set<string>): EnvSyncPlan
 
     const isNew = existingContent === null;
     const keyChanges: KeyChange[] = [];
+    let missingValues: string[];
 
     if (existingContent !== null) {
       const oldVars = parseEnvFile(existingContent);
-      const missingSet = new Set(missingValues);
+      // Only report keys as missing if the existing .dev.vars also lacks a value.
+      // Keys that couldn't be resolved but already have a value in .dev.vars are
+      // kept as-is — skip them from both missing warnings and key change diffs.
+      const unresolvedSet = new Set(unresolvedKeys);
+      missingValues = unresolvedKeys.filter(key => !oldVars.get(key));
       for (const [key, newVal] of resolvedVars) {
-        if (missingSet.has(key)) continue;
+        if (unresolvedSet.has(key)) continue;
         const oldVal = oldVars.get(key);
         if (oldVal !== newVal) {
           keyChanges.push({ key, oldValue: oldVal, newValue: newVal });
         }
       }
+    } else {
+      missingValues = unresolvedKeys;
     }
 
     if (isNew || keyChanges.length > 0 || missingValues.length > 0) {
diff --git a/src/lib/cloud-agent-sdk/session-manager.test.ts b/src/lib/cloud-agent-sdk/session-manager.test.ts
index 3019bcb34f..89dc7ec754 100644
--- a/src/lib/cloud-agent-sdk/session-manager.test.ts
+++ b/src/lib/cloud-agent-sdk/session-manager.test.ts
@@ -24,11 +24,16 @@ const mockSession = {
   canSend: true,
   canInterrupt: true,
   state: {
-    subscribe: jest.fn(() => () => {}),
+    subscribe: jest.fn(callback => {
+      callback();
+      return () => {};
+    }),
     getActivity: jest.fn(() => ({ type: 'idle' as const })),
     getStatus: jest.fn(() => ({ type: 'idle' as const })),
+    getCloudStatus: jest.fn(() => null),
     getQuestion: jest.fn(() => null),
     getSessionInfo: jest.fn(() => null),
+    getPermission: jest.fn(() => null),
   },
   storage: {},
 };
@@ -129,7 +134,10 @@ describe('createSessionManager', () => {
     mockSession.respondToPermission.mockClear();
     mockSession.canSend = true;
     mockSession.canInterrupt = true;
-    mockSession.state.subscribe.mockImplementation(() => () => {});
+    mockSession.state.subscribe.mockImplementation(callback => {
+      callback();
+      return () => {};
+    });
     mockSessionCallbacks.onQuestionAsked = undefined;
     mockSessionCallbacks.onQuestionResolved = undefined;
     mockSessionCallbacks.onPermissionAsked = undefined;
@@ -609,6 +617,56 @@ describe('createSessionManager', () => {
 
       expect(mockSession.interrupt).not.toHaveBeenCalled();
     });
+
+    it('does NOT call session.disconnect after interrupt', async () => {
+      const config = createMockConfig();
+      const mgr = createSessionManager(config);
+
+      await mgr.switchSession(kiloId('ses-1'));
+      await mgr.interrupt();
+
+      expect(mockSession.disconnect).not.toHaveBeenCalled();
+    });
+
+    it('disables canSendAtom immediately on interrupt', async () => {
+      const config = createMockConfig();
+      const mgr = createSessionManager(config);
+
+      await mgr.switchSession(kiloId('ses-1'));
+      // Verify canSend is true before interrupt
+      expect(atomValue<boolean>(config.store, mgr.atoms.canSend)).toBe(true);
+
+      // Call interrupt without awaiting — check synchronously after call
+      void mgr.interrupt();
+      // After calling interrupt (even before it resolves), canSend should be false
+      expect(atomValue<boolean>(config.store, mgr.atoms.canSend)).toBe(false);
+    });
+
+    it('disables canInterruptAtom immediately on interrupt', async () => {
+      const config = createMockConfig();
+      const mgr = createSessionManager(config);
+
+      await mgr.switchSession(kiloId('ses-1'));
+      expect(atomValue<boolean>(config.store, mgr.atoms.canInterrupt)).toBe(true);
+
+      void mgr.interrupt();
+      expect(atomValue<boolean>(config.store, mgr.atoms.canInterrupt)).toBe(false);
+    });
+
+    it('session remains usable after interrupt — send does not throw', async () => {
+      const config = createMockConfig();
+      const mgr = createSessionManager(config);
+
+      await mgr.switchSession(kiloId('ses-1'));
+      await mgr.interrupt();
+
+      // After interrupt, send should NOT throw — transport should still be alive
+      mockSession.send.mockResolvedValue({});
+      await expect(
+        mgr.send({ prompt: 'follow-up message', mode: 'code', model: 'claude-3-5-sonnet' })
+      ).resolves.not.toThrow();
+      expect(mockSession.send).toHaveBeenCalledTimes(1);
+    });
   });
 
   // -------------------------------------------------------------------------
diff --git a/src/lib/cloud-agent-sdk/session-manager.ts b/src/lib/cloud-agent-sdk/session-manager.ts
index 307da0b400..7d7ea6ef9f 100644
--- a/src/lib/cloud-agent-sdk/session-manager.ts
+++ b/src/lib/cloud-agent-sdk/session-manager.ts
@@ -601,11 +601,16 @@ function createSessionManager(config: SessionManagerConfig): SessionManager {
 
   async function interrupt(): Promise<void> {
     if (!currentSession) return;
+    // Eagerly disable send/interrupt to prevent the user from sending a
+    // message while the async interrupt HTTP call is in flight. We do NOT
+    // call disconnect() — interrupt stops the agent but keeps the transport
+    // alive so the user can continue the session.
+    store.set(canSendAtom, false);
+    store.set(canInterruptAtom, false);
     try {
       if (currentSession.canInterrupt) {
         await currentSession.interrupt();
       }
-      currentSession.disconnect();
       setIndicator({ type: 'info', message: 'Session stopped', timestamp: Date.now() });
     } catch {
       store.set(errorAtom, 'Failed to stop execution');