# Penpal

Write better messages to Claude, on your Mac. Draw on your screen and the picture goes into Claude's message box, keep your best prompts as snippets, and get guided step by step.

## Download
- Latest: [Penpal 1.0.8](https://www.santarow.com/downloads/Penpal-1.0.8.dmg) · macOS 14 or later
- Signed with Developer ID (Jason Chen, 92HZ963W7D) and notarized by Apple

## Verify your download (optional)
macOS checks Apple's notarization when you open the app. To check the file yourself:

    shasum -a 256 ~/Downloads/Penpal-1.0.8.dmg

It should print:

    c02ea4ae9bdeddcc19f73c518ac2644c723612fee42cfc72a0aac14cf8a89de2

## Releases
| Version | Date | Changes | SHA-256 |
|---|---|---|---|
| 1.0.8 | 2026-10-14 | Take to Chat, a new button in the dock: your Claude writes a short spoken briefing of the Claude Code session you're in and opens it as a new Claude chat, so you can talk it through by voice on your iPhone; Highlight, snippets and Enhance can send to Grok Bot's message box instead of Claude's (Settings › Highlight › Send to) | c02ea4ae9bdeddcc19f73c518ac2644c723612fee42cfc72a0aac14cf8a89de2 |
| 1.0.7 | 2026-10-08 | Enhance's Send checks that your prompt really arrived in Claude's message box; if it didn't, nothing is cleared, the prompt is copied, and Penpal says so; Recent asks: a clock button in the Enhance window lists your last 20 asks, and picking one opens it again with its words, notes, pictures and enhanced prompt | 844c4d91a141b935fa1586744170ef254dff53fd142393d373d64c7d8d2a6f8d |
| 1.0.6 | 2026-10-07 | Guide me sees your whole screen, so two windows side by side (like Vercel and Porkbun) both get rings; Settings › Guide me can limit it to the app in front; Guide me carries values from one page to the next (a DNS record Vercel shows becomes a "Type:" step on Porkbun's page, with a copy button); Highlight, snippets and Send only ever type into Claude's message box, and if it can't be found the picture or text stays on the clipboard and Penpal says so; Penpal keeps its data in its own folder, ~/Library/Application Support/Penpal | 3b7e3d2bce6183d2343b9fa985adfe914b02b3a96c74ee861ac4e478393bc3e2 |
| 1.0.5 | 2026-10-07 | Ask Guide me a question mid-guide and the answer goes into your steps; choose the model for Guide me and for Enhance in Settings › Magic; Guide me runs on Haiku 5.5 by default, so the first ring shows sooner; Guide me never guesses an address for you to type; move the Guide me panel, and tours of the page you're on; blue rings point things out, red rings are for you to click; tidier settings, in a clearer order, each saying what it does. (1.0.4 was never published; its changes are in this release.) | 6f1a426de89478db4f0c7945545ad68af5dbd6c51fecd910e34d6b3fecc387b8 |
| 1.0.3 | 2026-10-07 | Enhance uses exactly the model you pick (Sonnet 5.5, Opus 5.5, Haiku 5.5, or Haiku 4.5 for older Claude Code), and if your Claude Code can't run it, says so and uses the closest one; Search, New and Window sit at the top of the dock, under its header (move them back below Highlight in Settings › Dock) | ced3d30faefca5df0c52bd14d403855e8e03fc0a74ff3605e304ff6499f97157 |
| 1.0.2 | 2026-10-07 | Claude History (⌘Y) and Usage in the menu bar; pick the model Enhance uses in Settings › Enhance (Sonnet, Opus, or a fast Haiku); Enhance rewrites your ask even when it's a question; drag the folded Enhance pill anywhere and it stays; Search, New and Window can sit above Highlight in the dock (Settings › Dock) | 75cb80c7fff9c367dcc0e5bec693e4695814e25d5b7bf7e479559b230fa81eba |
| 1.0.1 | 2026-10-06 | Penpal stays on screen until you hide it (switching apps or opening Settings no longer hides the dock); whatever you clicked last comes to the front; Fold sits in the top-right corner of the Enhance window; Guide me's numbers stay readable when two steps point at the same button; the Pen preview's sample text reads "this part" | f90e53187f7e92e65bf85bd86a0e4cd39d7aeaca8fbce06249b0069d8b3dd1a0 |
| 1.0 | 2026-10-06 | First release | ff3b5b90b19eb54671f66856161f25683de74293a1a49da8fdc394074080ecaf |

## What it does
- Highlight: hold Control and Option and draw around anything on your screen; the picture goes into Claude's message box, numbered 🖼 1, 🖼 2. Nothing is sent until you press Return in Claude.
- Snippets: saved prompts, pasted from the dock or by typing ;name in Claude's message box.
- Search, New and Window: Claude's own session buttons, at the top of the dock.
- Guide me and Enhance: your own Claude, through Claude Code on your Mac. Guide me circles the steps on screen; Enhance turns a rough ask into a clear prompt.

## Privacy
- Sends nothing to SantaRow: no account, no analytics, no crash reports.
- Asks macOS for Accessibility, Screen Recording and, only for Claude History's Resume in Terminal, Apple Events.
- Details: https://www.santarow.com/privacy/#penpal