[FEATURE] drop image N from context" or "auto-evict images older than X messages

Preflight Checklist

• [x] I have searched existing requests and this feature hasn't been requested yet
• [x] This is a single feature request (not multiple features)

Problem Statement

An image in the conversation exceeds the dimension limit for many-image requests (2000px). Start a new session with fewer images.

Proposed Solution

drop image N from context" or "auto-evict images older than X messages

Alternative Solutions

_No response_

Priority

Critical - Blocking my work

Feature Category

CLI commands and flags

Use Case Example

_No response_

Additional Context

_No response_