[BUG] Offer alternative solutions when repeated bug fixes fail

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

Claude Code attempted several times to fix corruption in Excel spreadsheets, each time confirming the bugs were fixed when they were not. I had to suggest rebuilding the files from scratch, which immediately solved all issues.

What Should Happen?

after 2–3 failed attempts at the same approach, Claude should proactively offer a fundamentally different alternative rather than retrying variants of the same fix. This would also reduce unnecessary energy consumption from repeated failed attempts.
A better approach would have been to recognize earlier that incremental repairs to a corrupted file were unlikely to succeed and pivot to "rebuild from scratch" as an explicit alternative. Offering that option sooner (rather than after several failed attempts) would have saved time, energy, and frustration.

Error Messages/Logs

Steps to Reproduce

Steps to reproduce:

1. Have Claude modify an existing .xlsx file using openpyxl (e.g. "fix the data validation dropdowns")
2. Claude makes changes and confirms "fixed"
3. Open the file in Excel → "We found a problem with some content"
4. Ask Claude to fix it again → same result, same confirmation
5. Claude never proactively suggests rebuilding from scratch

The minimal reproducible case — openpyxl's data validation writer bloats sqref attributes across ~1024 columns whenever it loads and re-saves a file that already has data validations. Any .xlsx with data validation dropdowns will trigger this if you load it with load_workbook() and save().

Claude Model

None

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

I have no idea - I run Sonnet 4.6

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_