| name | readwise-chat |
| description | Chat with Readwise highlights using GPT-5.1 RAG. Use when the user wants to ask questions about their reading library, get summaries across documents, or have a conversation about their highlights. Triggers on "ask readwise", "chat about my highlights", "what do my notes say about", "summarize my reading on". |
| context | fork |
| agent | librarian |
| user-invocable | false |
Readwise Chat (RAG over Highlights)
Uses GPT-5.1 to answer questions with RAG over the user's full highlight library via WebSocket streaming.
Prerequisites
Chat requires session cookies (not API token). Check if configured:
grep SESSION_COOKIES ~/.readwise/env
If missing, run:
readwise-custom auth session
This launches Chrome, navigates to readwise.io/chat, and extracts httpOnly session cookies via CDP.
Commands
One-Shot Query
Streams the response to stdout as it arrives:
readwise-custom chat "What are my highlights about fiduciary duty?"
readwise-custom chat "Summarize my notes on proxy advisors"
readwise-custom chat "Compare what I've read about SEC regulation vs FINRA"
With JSON output (includes related highlights):
readwise-custom chat "What do my highlights say about broker-dealer regulation?" --json
Interactive REPL
Multi-turn conversation with context preserved:
readwise-custom chat-interactive
readwise-custom chat-interactive --model 5.1-thinking
Type exit to quit.
Conversation Management
readwise-custom chat-list
readwise-custom chat-get <id>
readwise-custom chat-delete <id>
readwise-custom chat-rename <id> "Better Title"
Model Options
| Model ID | Name | Use Case |
|---|
5.1 | Fast (default) | Quick answers, simple lookups |
5.1-thinking | Thinking | Complex synthesis, reasoning |
Chat vs Search
| Feature | readwise-custom chat | readwise readwise-search-highlights |
|---|
| Returns | Synthesized answer + highlights | Raw highlight matches |
| Model | GPT-5.1 RAG | Vector similarity |
| Auth | Session cookies | API token |
| Speed | ~3-10s (streaming) | ~2s |
| Highlights returned | Up to 69 | Top-N vector matches |
| Multi-turn | Yes (interactive) | No |
Use chat when: You want a synthesized answer, cross-document analysis, or conversational exploration.
Use search when: You want raw highlight matches, exact quotes, or structured data for further processing.
