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  # reasoning model

Type exit to quit.

Conversation Management

readwise-custom chat-list                           # List all conversations
readwise-custom chat-get <id>                       # Get conversation with messages
readwise-custom chat-delete <id>                    # Delete conversation
readwise-custom 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-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.