diff --git a/packages/app/src/components/message-input.tsx b/packages/app/src/components/message-input.tsx
index 9a5cf16ce..ee528dce8 100644
--- a/packages/app/src/components/message-input.tsx
+++ b/packages/app/src/components/message-input.tsx
@@ -950,18 +950,20 @@ export const MessageInput = forwardRef<MessageInputRef, MessageInputProps>(funct
           <View style={styles.leftButtonGroup}>
             {onPickImages && (
               <Tooltip delayDuration={0} enabledOnDesktop enabledOnMobile={false}>
-                <TooltipTrigger
-                  onPress={onPickImages}
-                  disabled={!isConnected || disabled}
-                  accessibilityLabel="Attach images"
-                  accessibilityRole="button"
-                  style={({ hovered }) => [
-                    styles.attachButton,
-                    hovered && styles.iconButtonHovered,
-                    (!isConnected || disabled) && styles.buttonDisabled,
-                  ]}
-                >
-                  <Paperclip size={buttonIconSize} color={theme.colors.foreground} />
+                <TooltipTrigger asChild>
+                  <Pressable
+                    onPress={onPickImages}
+                    disabled={!isConnected || disabled}
+                    accessibilityLabel="Attach images"
+                    accessibilityRole="button"
+                    style={({ hovered }) => [
+                      styles.attachButton,
+                      hovered && styles.iconButtonHovered,
+                      (!isConnected || disabled) && styles.buttonDisabled,
+                    ]}
+                  >
+                    <Paperclip size={buttonIconSize} color={theme.colors.foreground} />
+                  </Pressable>
                 </TooltipTrigger>
                 <TooltipContent side="top" align="center" offset={8}>
                   <Text style={styles.tooltipText}>Attach images</Text>
@@ -1203,7 +1205,7 @@ const styles = StyleSheet.create(((theme: any) => ({
   leftButtonGroup: {
     flexDirection: "row",
     alignItems: "flex-end",
-    gap: Platform.OS === "web" ? theme.spacing[2] : theme.spacing[1],
+    gap: theme.spacing[1],
   },
   rightButtonGroup: {
     flexDirection: "row",
diff --git a/packages/server/src/server/agent/providers/__tests__/claude-agent.event-stream.integration.test.ts b/packages/server/src/server/agent/providers/__tests__/claude-agent.event-stream.integration.test.ts
index cab8286aa..4d7f6cded 100644
--- a/packages/server/src/server/agent/providers/__tests__/claude-agent.event-stream.integration.test.ts
+++ b/packages/server/src/server/agent/providers/__tests__/claude-agent.event-stream.integration.test.ts
@@ -336,11 +336,7 @@ describe("Agent event stream redesign — integration", () => {
     const handle = await createSession({ cwdPrefix: "event-stream-interrupt-" });
 
     try {
-      const { turnId } = await handle.session.startTurn(
-        "write a very long essay about the history of computing",
-      );
-
-      // Use a single subscription to avoid missing events between unsubscribe/resubscribe
+      let turnId: string | null = null;
       const events = await new Promise<AgentStreamEvent[]>((resolve, reject) => {
         const collected: AgentStreamEvent[] = [];
         let interrupted = false;
@@ -352,10 +348,14 @@ describe("Agent event stream redesign — integration", () => {
 
         const unsubscribe = handle.session.subscribe((event) => {
           collected.push(event);
+          if (!turnId && event.type === "turn_started" && hasTurnId(event)) {
+            turnId = event.turnId;
+          }
 
           // Once we see turn_started, fire the interrupt
           if (
             !interrupted &&
+            turnId &&
             event.type === "turn_started" &&
             hasTurnId(event) &&
             event.turnId === turnId
@@ -365,14 +365,37 @@ describe("Agent event stream redesign — integration", () => {
           }
 
           // Resolve when we get a terminal event for this turn
-          if (isTerminalEvent(event) && hasTurnId(event) && event.turnId === turnId) {
+          if (turnId && isTerminalEvent(event) && hasTurnId(event) && event.turnId === turnId) {
             clearTimeout(timeout);
             unsubscribe();
             resolve(collected);
           }
         });
+
+        void handle.session
+          .startTurn("write a very long essay about the history of computing")
+          .then((result) => {
+            if (turnId && turnId !== result.turnId) {
+              clearTimeout(timeout);
+              unsubscribe();
+              reject(
+                new Error(
+                  `Observed turn_started for ${turnId} but startTurn returned ${result.turnId}`,
+                ),
+              );
+              return;
+            }
+            turnId = result.turnId;
+          })
+          .catch((error) => {
+            clearTimeout(timeout);
+            unsubscribe();
+            reject(error);
+          });
       });
 
+      expect(turnId).toBeDefined();
+
       // turn_canceled or turn_failed arrives for that turnId
       const terminal = events.find(
         (e) =>