Readwise Chat

---
name: readwise-chat
description: "Use when the user asks a QUESTION of their reading library rather than for a keyword lookup — 'ask readwise', 'chat about my highlights', 'what do my notes say about X', 'summarize my reading on X', 'what have I read about proxy advisors', 'compare what I've read about X vs Y', 'what's my take on X based on what I've read', 'pull together my highlights on X'. Use proactively for synthesis across many documents. NOT for finding a specific highlight by keyword — use readwise-search instead."
context: fork
agent: librarian
user-invocable: false
---

# Readwise Chat (RAG over Highlights)

**What this skill carries** — grep `references/` for any subject the names below miss:
!`d=${CLAUDE_SKILL_DIR}; command -v skill-toc >/dev/null 2>&1 && exec skill-toc "$d"; s=$HOME/.claude/skills/plugin-utils/bin/skill-toc; [ -x "$s" ] && exec "$s" "$d"; echo "(skill-toc unavailable: references and scripts are NOT listed here — install the plugin-utils plugin, or start a new session so its bin/ reaches PATH)"`

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:

```bash
grep SESSION_COOKIES ~/.readwise/env
```

If missing, run:

```bash
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:

```bash
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):

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

### Interactive REPL

Multi-turn conversation with context preserved:

```bash
readwise-custom chat-interactive
readwise-custom chat-interactive --model 5.1-thinking  # reasoning model
```

Type `exit` to quit.

### Conversation Management

```bash
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.