Fix conversation context loss in Addie chat

[bokelley]

Summary

• Fixed Addie losing conversation context by using proper Claude API message turns instead of flattening thread history into a single string
• Claude now receives actual user/assistant message turns, which it understands as real conversation context

Problem

Addie was losing context mid-conversation. When a user asked follow-up questions, Addie would forget what was just discussed and ask clarifying questions unnecessarily.

Root cause: Conversation history was being flattened into a single user message string:

Previous messages in thread:
User: Can you help me with AdMesh?
Addie: AdMesh looks like a strong prospect...

Current message: an outreach message would be great!

Claude treats this as informational text, not actual conversation context.

Solution

Created buildMessageTurns() function that converts history into proper alternating message turns:

[
  { role: 'user', content: 'Can you help me with AdMesh?' },
  { role: 'assistant', content: 'AdMesh looks like a strong prospect...' },
  { role: 'user', content: 'an outreach message would be great!' }
]

Claude's API treats this as actual conversation, preserving context.

Test plan

• Unit tests for buildMessageTurns() covering edge cases
• All existing tests pass (153 tests)
• TypeScript compiles with no errors
• Manual testing in Slack to verify context is preserved

🤖 Generated with Claude Code