Quick post today, with relevance to virtually no one, but I googled it and came up empty so might as well write it down.

The onset of summer has meant much less regular time in front of the computer. Instead I’ve been carrying my iPad, and giving it the 20th try as a lightweight productivity device. I’m running the iPadOS 26 Developer Beta, which seems to be moving more in the MacOS direction, so maybe we’ll get there.

I have a Raspberry Pi that I plan to set up with VS Code Server for remote code editing, and it’s set up with a Cloudflare Tunnel for remote SSH access, which requires proxying through the cloudflared client.

The following assumes you already have a CF tunnel set up for SSH. If not you should probably look into Tailscale instead. I would if I wasn’t already set up with Cloudflare.

Here’s how I went about setting up iSH on my iPad to make everything work.

  1. Install iSH, which is a piece of wizardry that gives you an x86 Alpine Linux shell on your iPad.

  2. Install required packages:

     apk add openssh-client curl nano

    At this point ssh [email protected] will fail with a timeout error.

    Since we’re in a full Linux shell, we can use the x86 cloudflared binary to proxy the connection, just as we would on any other Linux system.

  3. Create a user bin directory to hold the cloudflared binary:

     mkdir ~/bin && cd ~/bin

  4. Grab the latest x86 (32 bit) binary from GitHub. The current release is 2025.7.0, you’ll want to update the curl command below to the latest linux-386 version:

     curl -LO https://github.com/cloudflare/cloudflared/releases/download/2025.7.0/cloudflared-linux-386

  5. Tell SSH to proxy connections to your.cloudflare.tunnel through the cloudflared client:

     nano ~/.ssh/config

    Add the following:

     Host your.cloudflare.tunnel
 ProxyCommand /root/bin/cloudflared-linux-386 access ssh --hostname %h

  6. ssh your.cloudflare.tunnel should now work!

iSH is not the most practical way to work on a remote machine, but this is sufficient for logging in for the occasional need. Have fun!