[Bug] Image upload fails when combined context size exceeds 20MB limit

Bug Description
Today I discovered a bug in a different session - I'd been working all day and started hitting errors saying that 20MB screenshot / image uploads were being hit.... I debugged and confirmed the images were like 500KB - turns out that it must be image size + context size, b/c after compaction the screenshots all work fine.

Environment Info

• Platform: darwin
• Terminal: Apple_Terminal
• Version: 2.1.81
• Feedback ID: 2ff6c182-588e-4984-8cda-257757f194c7

Errors

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