[BUG] Windows Alt+V image paste fails once after idle, immediate second press succeeds (v2.1.212)

What's Wrong?

On native Windows, image paste has a repeatable cold/idle-cycle failure:

• After starting Claude Code, or after it has been idle for a long period, the first Alt+V image paste reports approximately no image found / clipboard is empty and attaches nothing.
• Without changing the clipboard, an immediate second Alt+V succeeds and inserts [Image #N].
• After that successful retry, later image pastes usually work on the first press for a while.
• After another long idle period, the same first-fails/second-succeeds cycle returns.

This still reproduces on Claude Code 2.1.212. It closely matches closed issue #59161, which was closed as stale/not planned rather than with a confirmed follow-up fix. It is distinct from #69234 because retrying inside the same session succeeds here.

What Should Happen?

When the Windows clipboard contains a screenshot, the first Alt+V press should attach the image. Image paste should not require a warm-up attempt after startup or idle time.

Error Messages/Logs

The transient message is approximately no image found / clipboard is empty; the exact wording was not captured yet. No debug log is attached to this initial report.

Steps to Reproduce

1. Run Claude Code on Windows and leave the session idle long enough for the cold behavior to return.
2. Capture a screenshot to the clipboard.
3. Press Alt+V once.
4. Observe that no image is attached and a no-image/empty-clipboard message appears.
5. Do not change the clipboard; immediately press Alt+V again.
6. Observe that the same image now attaches as [Image #N].
7. Paste additional screenshots shortly afterward; they generally succeed on the first press.
8. After a long idle period, repeat the sequence and observe the first failure again.

Environment

• Claude Code version: 2.1.212 (Claude Code)
• Operating system: Windows 11 Pro 10.0.26200
• Terminal: Windows Terminal
• Shell: Git Bash / MINGW64 (/bin/bash.exe)
• Keybindings: no user ~/.claude/keybindings.json
• Model: not relevant / multiple
• Platform: first-party Claude Code session
• Regression: yes; v2.1.141 release notes stated that Windows Alt+V no image found behavior was fixed, but the cold/idle retry pattern remains in 2.1.212
• Last known working version: unknown

Additional Information

The symptom strongly suggests a cold-path initialization or timing problem in the Windows clipboard image reader, but that is only a hypothesis. The useful discriminator is that the clipboard is unchanged and the immediate second read succeeds in the same session.

Related:

• #59161 — exact first-fails/second-succeeds pattern, now closed
• #69234 — different pattern where all retries fail until a new session
• v2.1.141 release note: “Fixed Windows Alt+V image paste reporting ‘no image found’ when the clipboard contains a screenshot.”

Preflight

• [x] Searched existing issues; the exact matching issue is closed and asks current reproductions to be filed again.
• [x] This report covers one bug.
• [x] Reproduces on the latest installed Claude Code version, 2.1.212.