Pasting screenshots into Claude Code over SSH

A developer documented a workaround for pasting screenshots into Claude Code over SSH by combining the clipssh CLI tool, a macOS Shortcuts automation, and SSH connection multiplexing. The setup uses clipssh's Bash script to copy an image to a temporary file on the remote host at CLIPSSH_REMOTE_DIR=/tmp/claude-image-clipboard, and adds ControlMaster auto with ControlPersist 4h in ~/.ssh/config to stop 1Password from prompting for SSH approval on each invocation.

I should soon be done with kicking Claude out of my personal MacBook to a local box. One of the first things I missed is the ability to paste screenshots with ⌃ V : the remote terminal doesn’t know about my clipboard. I wanted my solution to look like this: For the transport part, turns out Samuel Lawrentz had a similar need and published a CLI tool called clipssh https://github.com/samuellawrentz/clipssh : basically a Bash script that writes the image to a temporary file and copies it to the remote host. I didn’t want to install this with a package manager, so I just stuck the main script https://github.com/samuellawrentz/clipssh/blob/main/clipssh in .local/bin . The second part is a shortcut in the Shortcuts app that comes into play after I’d already captured the screenshot: Shottr is now the frontmost app and pressing expand the path so pngpaste a dependency of clipssh is there export PATH="/opt/homebrew/bin:$HOME/.local/bin:$PATH" export CLIPSSH HOST="username@100.113.x.x" export CLIPSSH REMOTE DIR="/tmp/claude-image-clipboard" sleep 0.3 dismiss Shottr auto copies the screenshot to my local clipboard osascript -e 'tell application "System Events" to key code 53' sleep 0.3 clipssh One thing left. 1Password kept prompting me to approve the SSH connection each time I invoked this, so I made the connection persist for 4 hours in ~/.ssh/config : Host 100.113.x.x ControlMaster auto ControlPath ~/.ssh/cm-%C ControlPersist 4h