diff --git a/web/src/client/components/session-card.ts b/web/src/client/components/session-card.ts
index cc528fbe..073c65a7 100644
--- a/web/src/client/components/session-card.ts
+++ b/web/src/client/components/session-card.ts
@@ -27,6 +27,7 @@ export class SessionCard extends LitElement {
   @property({ type: Object }) session!: Session;
   @state() private killing = false;
   @state() private killingFrame = 0;
+  @state() private hasEscPrompt = false;
 
   private killingInterval: number | null = null;
 
@@ -47,6 +48,10 @@ export class SessionCard extends LitElement {
     );
   }
 
+  private handleEscPromptChange(event: CustomEvent) {
+    this.hasEscPrompt = event.detail.hasEscPrompt;
+  }
+
   private async handleKillClick(e: Event) {
     e.stopPropagation();
     e.preventDefault();
@@ -151,10 +156,9 @@ export class SessionCard extends LitElement {
   render() {
     return html`
       <div
-        class="bg-vs-bg border border-vs-border rounded shadow cursor-pointer overflow-hidden ${this
-          .killing
+        class="bg-vs-bg rounded shadow cursor-pointer overflow-hidden ${this.killing
           ? 'opacity-60'
-          : ''}"
+          : ''} ${this.hasEscPrompt ? 'border-2 border-orange-500' : 'border border-vs-border'}"
         @click=${this.handleCardClick}
       >
         <!-- Compact Header -->
@@ -211,6 +215,7 @@ export class SessionCard extends LitElement {
                   .sessionId=${this.session.id}
                   class="w-full h-full"
                   style="pointer-events: none;"
+                  @esc-prompt-change=${this.handleEscPromptChange}
                 ></vibe-terminal-buffer>
               `}
         </div>
diff --git a/web/src/client/components/vibe-terminal-buffer.ts b/web/src/client/components/vibe-terminal-buffer.ts
index 3345a63a..c96d5285 100644
--- a/web/src/client/components/vibe-terminal-buffer.ts
+++ b/web/src/client/components/vibe-terminal-buffer.ts
@@ -25,6 +25,7 @@ export class VibeTerminalBuffer extends LitElement {
   @state() private error: string | null = null;
   @state() private displayedFontSize = 14;
   @state() private visibleRows = 0;
+  @state() private containsEscPrompt = false;
 
   private container: HTMLElement | null = null;
   private resizeObserver: ResizeObserver | null = null;
@@ -122,6 +123,9 @@ export class VibeTerminalBuffer extends LitElement {
       this.buffer = snapshot;
       this.error = null;
 
+      // Check if buffer contains "esc to interrupt" text
+      this.checkForEscPrompt();
+
       // Recalculate dimensions now that we have the actual cols
       this.calculateDimensions();
 
@@ -130,6 +134,35 @@ export class VibeTerminalBuffer extends LitElement {
     });
   }
 
+  private checkForEscPrompt() {
+    if (!this.buffer) {
+      this.containsEscPrompt = false;
+      return;
+    }
+
+    // Check if any line contains "esc to interrupt" (case insensitive)
+    const searchText = 'esc to interrupt';
+    const found = this.buffer.cells.some((row) => {
+      const lineText = row
+        .map((cell) => cell.char)
+        .join('')
+        .toLowerCase();
+      return lineText.includes(searchText);
+    });
+
+    if (found !== this.containsEscPrompt) {
+      this.containsEscPrompt = found;
+      // Dispatch event to notify parent
+      this.dispatchEvent(
+        new CustomEvent('esc-prompt-change', {
+          detail: { hasEscPrompt: found },
+          bubbles: true,
+          composed: true,
+        })
+      );
+    }
+  }
+
   private unsubscribeFromBuffer() {
     if (this.unsubscribe) {
       this.unsubscribe();