Chat session becomes permanently unusable when any past image exceeds 2000px limit

Bug

When a conversation contains any image that exceeds the 2000px dimension
limit for many-image requests, every subsequent message in that session
fails, even text-only messages. The entire chat history becomes
unreachable — users lose hours of context through one oversized screenshot
pasted earlier.

Repro

1. Start a Claude Code session
2. Paste any image > 2000px (e.g. a full-resolution screenshot)
3. Later in the same session, send a text-only message
4. Observe: `An image in the conversation exceeds the dimension limit for

many-image requests (2000px). Start a new session with fewer images.`

1. Session is now permanently broken until /clear, losing all context.

Why this matters

• The oversized image may have been pasted hours earlier.
• The error does not identify which image is the offender.
• /clear is the only workaround, which destroys all working context

(plans, file reads, todo lists, decisions).

• Users commonly paste full-resolution screenshots without knowing the

limit exists.

Requested behavior (any of these would fix it)

1. Auto-downscale images > 2000px on the client side before they enter

the transcript.

1. Skip/strip the offending image from the request payload on retry,

with a warning — do not block the entire session.

1. Persist chat history to disk automatically (autocommit-style), so

/clear does not mean total loss. Session could be resumable minus the
bad image.

1. At minimum: identify which image exceeds the limit and offer an

inline option to drop it from context.

Environment

• Claude Code (VS Code extension), Windows 11
• Model: Opus 4.7 (1M context)