Prepare the host before connecting from iPad
You need an awake Linux or Mac development host, a normal user account, a working SSH server, tmux and Claude Code installed and authenticated. Clone your project and check that it runs on the host first. Install Tailscale on the host and iPad and use an SSH client on the iPad.
Put both devices on a private network
Sign in to Tailscale on both devices and confirm that your network policy permits the iPad to reach the host’s SSH port. Connect to the host’s Tailscale address or configured DNS name. Standard OpenSSH over Tailscale can use your usual SSH keys; the separate Tailscale SSH feature has its own setup and authorization rules.
Connect and verify the destination
In the iPad SSH client, enter the private host address, username and authentication method. Verify the host key fingerprint against a trusted record before accepting it. The example checks the remote username and working directory. Replace devbox with your reachable host name; it is not a built-in address.
ssh user@devbox
whoami
pwdCommands are examples. Replace user, devbox, project paths and the example URL with your own values. Run file-transfer commands in a shell, not in the agent’s chat. Keep private links out of shared logs and shell history.
Start Claude Code inside tmux
Create or attach to a named tmux session, enter your project directory and launch Claude Code. Run these commands on the remote host after SSH login. If the named session already contains a running agent, continue that session rather than typing shell commands into its prompt. The project path below is an example.
tmux new-session -A -s ai
cd ~/project
claudeCommands are examples. Replace user, devbox, project paths and the example URL with your own values. Run file-transfer commands in a shell, not in the agent’s chat. Keep private links out of shared logs and shell history.
Detach, reconnect and recover
To detach from tmux, press Control+B, release both keys, then press D. Reconnect over SSH and attach to the same session with the example command. If it is missing, check whether the host restarted or the session ended. Reopen the project and use Claude Code’s resume options if necessary.
ssh user@devbox
tmux attach-session -t aiCommands are examples. Replace user, devbox, project paths and the example URL with your own values. Run file-transfer commands in a shell, not in the agent’s chat. Keep private links out of shared logs and shell history.
Preview the app and send useful feedback
A server’s localhost is not your iPad’s localhost. Use a deliberately configured private preview or SSH port forwarding to reach a development app; avoid exposing an unauthenticated development server publicly. Reproduce the problem on the iPad, capture the relevant screen and send the screenshot with the route, viewport and expected behavior.
Screenshot → Share2AI → your AI
- Install Share2AI on your iPhone, iPad or Mac. Open the app and activate or restore your subscription before using the share extension.
- Check the screenshot and hide passwords, personal messages and other sensitive details. On iPhone or iPad, open it in Photos, tap Share and select Share2AI. If needed, find it under More.
- Wait for the upload and the confirmation that the link was copied. Paste that fresh link into your AI conversation with a specific question. Do not open it yourself to test it first.
- Ask the agent to retrieve and inspect the screenshot once. If it needs a local attachment, download the image on the machine running the agent, then attach that saved file. A URL only works when the tool can fetch and process images.
Temporary access and privacy
Anyone with an active link can access the screenshot. Share2AI deletes its temporary copy after successful delivery or expiration; the initial lifetime is 30 minutes, and the app shows the applicable expiry. Removing metadata does not hide visible secrets. Copies downloaded to your server and data retained by the destination AI follow their own retention rules.
Troubleshooting and FAQ
The AI cannot open the link. What should I check?
Check whether it supports image input and outbound HTTPS. A text-only web fetcher may not pass image pixels to the model. If permitted, download once to the agent’s machine and attach the local image. Do not turn off security controls just to make a link work.
Why did the link stop working?
It may have been delivered already or expired. Opening it in a browser or downloading it with curl can use the one-time delivery. Create a fresh link for another delivery; keep a successfully downloaded local copy for the current task.
Can I send several screenshots or any file?
Share2AI handles one screenshot per upload. PNG and JPEG are supported; the Apple client can convert HEIC before uploading. Documents, archives and batches are outside the screenshot workflow.
Send the screenshot from where you are
Share a screenshot, copy its temporary link and bring visual context to your remote AI.
Share2AI costs $0.99 per month in the United States. The App Store shows your local price before purchase. There is no free trial. The subscription renews automatically until canceled in your Apple Account settings.