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What Does Your Road Warrior Kit Look Like? Here's How I Setup to Go On the Road

Road WarriorI’m traveling at the moment and before I left, I spent time preparing my road environment.  I’m curious how others handle these sorts of needs.

Home Access

It never fails that I’m away from home and need to get something stored on my home file servers.  While I keep a lot of stuff in the cloud, I do have several Synology boxes that keep photo, video, VM, documents, art files, and 3D files.  I do back them up to the cloud (B2) but it’s massively handy to login and grab a file.

On the other hand, it would be catastrophic if I had an intruder waltz into my home network, so any access needs to be secure.

My setup works like this:

  • I created a couple small VMs at different providers.  They only accept logins over SSH via public key.
  • My home IP is registered with a dynamic DNS provider.  So I can login to these VMs and then SSH to home.
  • At home, my router port-forwards a couple random ports to a pair of VMs.
  • These VMs only accept SSH from the two VMs in the cloud, and login is via public key only.
  • Once I’ve done the double hop (login to VM, login to home), I’m on my home network and can SSH for the file servers or whatever.

Once I find the file(s) I want, I copy them to Dropbox.  I have Dropbox running on one of the Synologies.  The file then appears on my laptop here on the road via Dropbox.

This setup protects against random SSH attacks, as they’d need to come from one of the two VMs.  It’s kind of triple factor authentication: they need to have something (my ssh key), know something (the ssh key passphrase), and be somewhere (come from one of the two VMs).

Remote Access

I have a couple systems I need to login to that are protected by CloudFlare firewall, etc.  Whitelisting a different IP every time I change hotel rooms is tedious, so I use a VPN.

I use the legendary roadwarrior VPN setup script from @Nyr to turn any VPS into a VPN server.  I like Spark Labs’ Viscosity on the laptop side.

This gives me the ability to connect to the VPN and then appear as one, consistent IP.  Plug that into CloudFlare and I’m good to go no matter where I am geographically.


This is a little thornier because of bandwidth.  I’d love to have my Mac streaming continuously to some backup in the sky, and I could do that with something like BackBlaze.  That would be great if I had fully backed up my system in the cloud before leaving, and then I’d just be topping off changes.  However, I didn’t do that and taking the whole multi-terabyte load into the sky now would take a lot longer than this trip.

I keep anything important on Dropbox or OneDrive (or iDrive, though I like it less than its competitors), so even if my laptop was swiped or destroyed by a meteor, I wouldn’t lose anything vital.  But there’s such a difference between “I think I have everything on Dropbox” and “I can do a restore at any time and be back to any exact point in time that I want”.

For the latter, I use an external HDD.  Obviously, if there was a fire or something, I could lose both laptop and backup drive…in that case, I’d fall back to cloud.  But for the “oh crap, my laptop just blew up and I’ve got a new one arriving tomorrow” scenario, it’s a good, well, backup.

What Are Your Tricks?

How do you setup for a road trip?  Any advice or tips to make digital life on the road easier?





1 Comment

  1. Mark:

    I use tailscale for remote access to my media server to stream via jellyfin. Plus I also have an external HDD which I clone before going away if I want a big collection or have limited internet.

    For my phone I clone my music collection onto an SD card, so its all local.

    Any other data generated, photos etc. Can be kept locally until going home or synced to a cloud provider if it wants backing up.

    This isn’t as sophisticated or complex as your setup and probably has flaws you’d find holes in. But given that nothing is too precious here and I have backups I’m happy with it.

    May 1, 2024 @ 1:30 pm | Reply

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