[FEATURE] Inline Drawing Mode for Chat Annotations

[srb-sd]

Preflight Checklist

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

Problem Statement

Summary

Add a simple drawing overlay that lets users annotate the chat interface directly, eliminating verbose "which part" conversations.

Problem

Current workflow is inefficient:

User: "About the API structure you mentioned... around 10 messages ago... the caching part..."
Claude: "Which part exactly?"
User scrolls, copies text, pastes...

→ Wastes 2-3 minutes per reference

Minimal Required Features

• Basic shapes: Circle, Rectangle, Arrow
• Freehand drawing
• Text labels
• 2-3 colors
• Eraser

NOT needed:

• Separate window
• Complex tools
• Export/import
• Layers or advanced features

Technical Implementation

• Overlay <canvas> element on chat DOM
• Capture to image on submit
• Claude already supports image analysis
• No backend changes needed

Impact

• 30-40% of conversations involve referencing previous messages
• Current: 2-3 min of "which part?" back-and-forth
• With this: 10 seconds to circle and send
• Result: ~2x conversation efficiency

Use Cases (Very Common)

1. Code review: Circle specific lines → "This looks wrong"
2. Option selection: Checkmark one suggestion out of many
3. Flow correction: Redraw arrows on architecture diagrams
4. Error identification: Underline problematic output
5. Clarification: Highlight confusing parts of explanations

Prior Art

Similar to:

• PDF annotation (Adobe, Preview)
• Screenshot markup (Windows Snipping Tool, macOS)
• Zoom/Teams whiteboard overlays

But in-context within the active conversation.

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Bottom line: Let users point instead of describing. Simple feature, massive productivity gain.

Proposed Solution

Solution

Inline Drawing Mode - Press hotkey to draw directly on chat:

1. Hotkey → Drawing overlay activates
2. Draw circle/arrow/annotation on any message
3. Enter → Send as annotated screenshot
4. Continue chatting

Alternative Solutions

Simple Drawing...
not complex...

1. drawing overlay on chat history
2. drawing on whiteboard (empty)

Priority

Critical - Blocking my work

Feature Category

Interactive mode (TUI)

Use Case Example

Example usage:

Claude shows 3 options:
  1. Redis caching
  2. In-memory cache  ← [USER CIRCLES THIS + ARROW + "This one!"]
  3. CDN caching

User just draws instead of typing:
"I mean the second option, the in-memory one you mentioned..."

Additional Context