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 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 chat "What are my highlights about fiduciary duty?"
readwise chat "Summarize my notes on proxy advisors"
readwise chat "Compare what I've read about SEC regulation vs FINRA"

With JSON output (includes related highlights):

readwise chat "What do my highlights say about broker-dealer regulation?" --json

Interactive REPL

Multi-turn conversation with context preserved:

readwise chat-interactive
readwise chat-interactive --model 5.1-thinking  # reasoning model

Type exit to quit.

Conversation Management

readwise chat-list                           # List all conversations
readwise chat-get <id>                       # Get conversation with messages
readwise chat-delete <id>                    # Delete conversation
readwise chat-rename <id> "Better Title"     # Rename conversation

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 chat	readwise search
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.