diff --git a/src/cli/App.tsx b/src/cli/App.tsx
index 64a2a60..8fed89e 100644
--- a/src/cli/App.tsx
+++ b/src/cli/App.tsx
@@ -2054,13 +2054,37 @@ export default function App({
   }, []);
 
   const handleInterrupt = useCallback(async () => {
-    // If we're executing client-side tools, abort them locally instead of hitting the backend
-    // Don't show "Stream interrupted" banner - the tool result will show "Interrupted by user"
+    // If we're executing client-side tools, abort them AND the main stream
     if (isExecutingTool && toolAbortControllerRef.current) {
       toolAbortControllerRef.current.abort();
+
+      // ALSO abort the main stream - don't leave it running
+      buffersRef.current.abortGeneration =
+        (buffersRef.current.abortGeneration || 0) + 1;
+      const toolsCancelled = markIncompleteToolsAsCancelled(buffersRef.current);
+
+      // Show interrupt feedback (yellow message if no tools were cancelled)
+      if (!toolsCancelled) {
+        appendError("Stream interrupted by user", true);
+      }
+
+      if (abortControllerRef.current) {
+        abortControllerRef.current.abort();
+        abortControllerRef.current = null;
+      }
+
+      userCancelledRef.current = true; // Prevent dequeue
       setStreaming(false);
       setIsExecutingTool(false);
       refreshDerived();
+
+      // Delay flag reset to ensure React has flushed state updates before dequeue can fire.
+      // Use setTimeout(50) instead of setTimeout(0) - the longer delay ensures React's
+      // batched state updates have been fully processed before we allow the dequeue effect.
+      setTimeout(() => {
+        userCancelledRef.current = false;
+      }, 50);
+
       return;
     }
 
@@ -2077,7 +2101,13 @@ export default function App({
       // Prevent multiple handleInterrupt calls while state updates are pending
       setInterruptRequested(true);
 
-      // Abort the stream via abort signal
+      // Set interrupted flag FIRST, before abort() triggers any async work.
+      // This ensures onChunk and other guards see interrupted=true immediately.
+      buffersRef.current.abortGeneration =
+        (buffersRef.current.abortGeneration || 0) + 1;
+      const toolsCancelled = markIncompleteToolsAsCancelled(buffersRef.current);
+
+      // NOW abort the stream - interrupted flag is already set
       if (abortControllerRef.current) {
         abortControllerRef.current.abort();
         abortControllerRef.current = null; // Clear ref so isAgentBusy() returns false
@@ -2089,7 +2119,6 @@ export default function App({
       // Stop streaming and show error message (unless tool calls were cancelled,
       // since the tool result will show "Interrupted by user")
       setStreaming(false);
-      const toolsCancelled = markIncompleteToolsAsCancelled(buffersRef.current);
       if (!toolsCancelled) {
         appendError("Stream interrupted by user", true);
       }
@@ -2111,13 +2140,13 @@ export default function App({
         });
 
       // Reset cancellation flags after cleanup is complete.
-      // This allows the dequeue effect to process any queued messages.
-      // We use setTimeout to ensure React state updates (setStreaming, etc.)
-      // have been processed before the dequeue effect runs.
+      // Use setTimeout(50) instead of setTimeout(0) to ensure React has fully processed
+      // the streaming=false state before we allow the dequeue effect to start a new conversation.
+      // This prevents the "Maximum update depth exceeded" infinite render loop.
       setTimeout(() => {
         userCancelledRef.current = false;
         setInterruptRequested(false);
-      }, 0);
+      }, 50);
 
       return;
     } else {
diff --git a/src/cli/helpers/accumulator.ts b/src/cli/helpers/accumulator.ts
index 18f38ed..4e843b1 100644
--- a/src/cli/helpers/accumulator.ts
+++ b/src/cli/helpers/accumulator.ts
@@ -73,6 +73,7 @@ export type Buffers = {
   pendingRefresh?: boolean; // Track throttled refresh state
   interrupted?: boolean; // Track if stream was interrupted by user (skip stale refreshes)
   commitGeneration?: number; // Incremented when resuming from error to invalidate pending refreshes
+  abortGeneration?: number; // Incremented on each interrupt to detect cancellation across async boundaries
   usage: {
     promptTokens: number;
     completionTokens: number;
@@ -92,6 +93,7 @@ export function createBuffers(): Buffers {
     toolCallIdToLineId: new Map(),
     lastOtid: null,
     commitGeneration: 0,
+    abortGeneration: 0,
     usage: {
       promptTokens: 0,
       completionTokens: 0,
diff --git a/src/cli/helpers/stream.ts b/src/cli/helpers/stream.ts
index 28e54f9..8fea099 100644
--- a/src/cli/helpers/stream.ts
+++ b/src/cli/helpers/stream.ts
@@ -56,12 +56,22 @@ export async function drainStream(
   // Track if we triggered abort via our listener (for eager cancellation)
   let abortedViaListener = false;
 
+  // Capture the abort generation at stream start to detect if handleInterrupt ran
+  const startAbortGen = buffers.abortGeneration || 0;
+
   // Set up abort listener to propagate our signal to SDK's stream controller
   // This immediately cancels the HTTP request instead of waiting for next chunk
   const abortHandler = () => {
     abortedViaListener = true;
     // Abort the SDK's stream controller to cancel the underlying HTTP request
-    if (stream.controller && !stream.controller.signal.aborted) {
+    if (!stream.controller) {
+      debugWarn(
+        "drainStream",
+        "stream.controller is undefined - cannot abort HTTP request",
+      );
+      return;
+    }
+    if (!stream.controller.signal.aborted) {
       stream.controller.abort();
     }
   };
@@ -80,6 +90,15 @@ export async function drainStream(
     for await (const chunk of stream) {
       // console.log("chunk", chunk);
 
+      // Check if abort generation changed (handleInterrupt ran while we were waiting)
+      // This catches cases where the abort signal might not propagate correctly
+      if ((buffers.abortGeneration || 0) !== startAbortGen) {
+        stopReason = "cancelled";
+        // Don't call markIncompleteToolsAsCancelled - handleInterrupt already did
+        queueMicrotask(refresh);
+        break;
+      }
+
       // Check if stream was aborted
       if (abortSignal?.aborted) {
         stopReason = "cancelled";
@@ -321,11 +340,14 @@ export async function drainStreamWithResume(
   );
 
   // If stream ended without proper stop_reason and we have resume info, try once to reconnect
+  // Only resume if we have an abortSignal AND it's not aborted (explicit check prevents
+  // undefined abortSignal from accidentally allowing resume after user cancellation)
   if (
     result.stopReason === "error" &&
     result.lastRunId &&
     result.lastSeqId !== null &&
-    !abortSignal?.aborted
+    abortSignal &&
+    !abortSignal.aborted
   ) {
     // Preserve the original error in case resume fails
     const originalFallbackError = result.fallbackError;