Claude Desktop "Open" attach picks wrong file content despite showing correct filename in confirmation dialog

Status Closed — not planned
Maintainer reply None cached
Activity 1 comment · opened Sep 14, 2026 · closed Sep 17, 2026

Environment:

  • Windows 11 Home, build 10.0.26200
  • Claude Desktop (version: check Settings > About)
  • Reproduced across a full shutdown/reboot, not a transient state issue

Description:
Right-clicking Open or double-clicking a .csv file in File Explorer launches Claude Desktop and shows a correct "Attach '<filename>' to this session?" confirmation dialog naming the actual file clicked. But the content that lands in the chat after clicking Attach is from a different, unrelated file, not the one named in the dialog or the one clicked.

Steps to reproduce:

  1. In File Explorer, right-click a .csv file and choose Open (or double-click it).
  2. Claude Desktop opens and shows "Attach '<correct filename>' to this session?"
  3. Click Attach.
  4. The content in the chat is from a different file than the one named.

Confirmed NOT the cause (ruled out directly):

  • File corruption: read the file directly off disk outside any app; content is correct.
  • Windows file-type association hijack: checked four times via registry (.md and .csv, both extension-to-progid mapping and the actual shell open command). All clean.
  • Stuck app/OS state: persisted across a full shutdown and reboot.

Context: started shortly after ~100 duplicate CSV files were downloaded into Downloads in one session (a separate, since-fixed bug in an unrelated tool). The wrong file that gets attached appears to be from that same episode, suggesting a stale reference or cache inside Claude Desktop's own attach/file-picker logic.

Workaround: right-click "Open with," choosing Notepad or Excel explicitly, works correctly. Only plain Open/double-click triggers the wrong-content behavior.

View original on GitHub ↗

This issue has 1 comment on GitHub. Read the full discussion on GitHub ↗