Paste Images into Claude Code Over SSH with a Raycast Script

The Problem

Claude Code running on a remote machine over SSH can read local files on that machine. It cannot receive images pasted from your Mac's clipboard — the paste never crosses the SSH boundary.

The workaround: upload the image to the remote machine first, then paste the file path. Claude reads the path, loads the file.

The Script

A single Raycast Script Command handles the whole thing:

1. Copy an image to your clipboard (Cmd-Ctrl-Shift-4 for a region, or copy from anywhere)
2. Trigger the hotkey
3. The image is streamed to /tmp/ on the remote machine via Tailscale SSH
4. The bare remote path replaces your clipboard contents
5. Paste into your Claude Code session

Cmd-Ctrl-Shift-4
  → hotkey
  → Copied: /tmp/cc-paste-20260617-143201-12345.png
  → ⌘V into SSH session

Claude picks up the path with its Read tool. No extra steps.

Setup

brew install pngpaste

Grab the script from the agents-in-a-box repo, drop it into your Raycast Script Commands directory, and update REMOTE_HOST to match your SSH alias.

In Raycast: Settings → Extensions → Script Commands → add your scripts directory → bind a hotkey.

What it checks before transferring

• pngpaste installed
• tailscale running
• Remote peer online
• Clipboard actually contains an image (aborts with a HUD error if not)
• Remote file is non-empty after write (verifies the transfer)

Local temp file is cleaned up via trap on exit regardless of outcome.

Requirements

• macOS with Raycast
• pngpaste (brew install pngpaste)
• Tailscale with the remote host reachable
• Key-based SSH auth to the remote (no password prompts)