Chat History Deleted When Opening Project Folder

[colbyboles]

Bug Report: Chat History Deleted When Opening Project Folder

Issue Description

Chat history from a previous session was automatically deleted/lost when opening a project folder. This occurred without any warning or user confirmation.

Expected Behavior

• Chat history should persist when opening/closing project folders
• If chat history needs to be cleared, user should be prompted for confirmation
• Chat history should be accessible regardless of which folder/project is open

Actual Behavior

• Opened project folder /Users/cboles/dev/batscrape created by chat
• Previous chat history related to building this project disappeared
• No warning or confirmation dialog was shown
• Unable to recover the conversation history

Steps to Reproduce

1. Start a chat session without an open project and have a conversation (e.g., building a project)
2. Open the project folder to see what has been built
3. Observe that previous chat history is missing

Environment

• OS: macOS 25.0.0 (Darwin)
• Shell: /bin/zsh
• Project: batscrape (Python project)

Impact

• Lost context and conversation history
• Unable to reference previous discussions about implementation decisions
• Poor user experience - feels like data loss

Additional Notes

This is a critical UX issue. Chat history is valuable context that users rely on, and losing it without warning is problematic.

Suggested Fix

• Persist chat history per workspace/project
• Warn user before clearing/archiving old chat history
• Provide a way to recover or view archived chat history
• Consider linking chat history to project folders/workspaces so context is maintained