Image attachments silently fail to upload when message has no text

Summary

Image attachments silently fail to upload when a message contains no accompanying text. No error is shown. The filenames appear to be sent as plain text instead of as actual attachments, so the model/recipient never receives the images.

Expected behavior

Images should upload regardless of whether text accompanies them — or, if an upload fails, an error should surface to the user.

Actual behavior

• Attach one or more images, send with no text → images do not upload, no error shown.
• The user believes the images were shared; they were not.
• When the filenames are later referenced, they appear as bare filenames (e.g. 20260531_175753...jpg) lacking the usual upload hash-prefix (e.g. 797b9709-20260531_...jpg) that successful uploads carry.

Steps to reproduce

1. Attach one or more image files to a message.
2. Do not type any text.
3. Send.
4. → Images are not uploaded; the model reports never receiving them; no error is displayed.

Workaround

Add any text alongside the image(s). In one session, ~13 image sends that included a short caption all uploaded successfully; the only two that failed were sent with no text.

Impact

Silent data loss. The user reasonably believes images were shared. The failure was only caught because the model explicitly reported not seeing the images.

Environment

• Claude Code on Windows 11 (desktop)

Related

The built-in /bug command also failed to submit this report, returning "Couldn't send feedback. Please try again." (filed/encountered separately).