diff --git a/src/core/task/Task.ts b/src/core/task/Task.ts
index 5fcfde37ef..8c2fa95f4e 100644
--- a/src/core/task/Task.ts
+++ b/src/core/task/Task.ts
@@ -1588,8 +1588,24 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 		}
 	}
 
-	async handleTerminalOperation(terminalOperation: "continue" | "abort") {
+	/**
+	 * Handle terminal operations (continue/abort) with optional user message.
+	 *
+	 * When the user sends a message while a command is running (command_output ask),
+	 * we need to both continue the terminal AND resolve the pending ask with the
+	 * user's message. This prevents the UI from hanging.
+	 *
+	 * @param terminalOperation - "continue" to proceed or "abort" to kill the command
+	 * @param text - Optional user message text
+	 * @param images - Optional user message images
+	 */
+	async handleTerminalOperation(terminalOperation: "continue" | "abort", text?: string, images?: string[]) {
 		if (terminalOperation === "continue") {
+			// If user provided a message, resolve the pending ask with their message
+			// This allows the user to provide feedback while the command runs
+			if (text || (images && images.length > 0)) {
+				this.handleWebviewAskResponse("messageResponse", text, images)
+			}
 			this.terminalProcess?.continue()
 		} else if (terminalOperation === "abort") {
 			this.terminalProcess?.abort()
diff --git a/src/core/webview/webviewMessageHandler.ts b/src/core/webview/webviewMessageHandler.ts
index 0df014b49a..5d4ac0bebc 100644
--- a/src/core/webview/webviewMessageHandler.ts
+++ b/src/core/webview/webviewMessageHandler.ts
@@ -655,7 +655,11 @@ export const webviewMessageHandler = async (
 
 		case "terminalOperation":
 			if (message.terminalOperation) {
-				provider.getCurrentTask()?.handleTerminalOperation(message.terminalOperation)
+				// Pass text/images if user sent a message with the terminal operation
+				// This allows the user to provide additional context when continuing
+				// a long-running command
+				const resolved = await resolveIncomingImages({ text: message.text, images: message.images })
+				provider.getCurrentTask()?.handleTerminalOperation(message.terminalOperation, resolved.text, resolved.images)
 			}
 			break
 		case "clearTask":
diff --git a/webview-ui/src/components/chat/ChatView.tsx b/webview-ui/src/components/chat/ChatView.tsx
index 6f3ee16ec1..055c939629 100644
--- a/webview-ui/src/components/chat/ChatView.tsx
+++ b/webview-ui/src/components/chat/ChatView.tsx
@@ -616,11 +616,26 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 					switch (
 						clineAskRef.current // Use clineAskRef.current
 					) {
+						case "command_output":
+							// For command_output, send terminalOperation with user's message
+							// instead of askResponse. This allows the command to continue
+							// running in the background while keeping the UI responsive.
+							// The user's message is passed to the backend to be used as
+							// additional context when the command finishes.
+							vscode.postMessage({
+								type: "terminalOperation",
+								terminalOperation: "continue",
+								text,
+								images,
+							})
+							// Clear input but don't fully reset UI to avoid hang
+							setInputValue("")
+							setSelectedImages([])
+							return // Don't call handleChatReset
 						case "followup":
 						case "tool":
 						case "browser_action_launch":
 						case "command": // User can provide feedback to a tool or command use.
-						case "command_output": // User can send input to command stdin.
 						case "use_mcp_server":
 						case "completion_result": // If this happens then the user has feedback for the completion result.
 						case "resume_task":