Agent wasted 2+ hours repeating impossible iOS build without reporting failure

What happened

During a coding session, I asked the agent to build a Flutter iOS app to my physical iPhone. The agent attempted CLI-based builds (flutter run, xcodebuild) which kept hanging due to a known Xcode 26 + CocoaPods compatibility issue (xcodebuild -list infinite hang).

Instead of reporting "this is not possible via CLI" after the first failure, the agent:

• Repeated the same failing commands for over 2 hours
• Tried killing processes and retrying the same approach ~10+ times
• Consumed significant tokens on each attempt
• Never clearly reported that CLI iOS device builds were not feasible in this environment

Expected behavior

After the first or second failure, the agent should have:

1. Clearly stated "I cannot complete iOS device builds via CLI due to xcodebuild hanging"
2. Provided manual instructions for the user to build via Xcode GUI
3. Stopped attempting and moved on

Impact

• 2+ hours of user time wasted
• Large amount of tokens consumed with zero result
• User frustration

Environment

• macOS 26.3.1, Xcode 26.1.1, CocoaPods 1.16.2
• Flutter, iOS physical device build
• Claude Code CLI