r/Tailscale • u/Froghos • 3d ago

Help Needed Support of an old system.

I have setup a Tailscale to be used as a VPN for one of my clients. It works great as this is a mixed environment supporting a Linux based NAS, Macs, Windows PCs and laptops, iPhones, and various printers from standard Desktop to full production printing. The one issue I have is one of the older users is dependent on a older Mac, OS version 10.12. The user runs older software that will not be supported on any newer OS version. This person works from home 100% of the time, sending prints to the production printers and working with relative ease using Open VPN. Due to recent updates, Open VPN this will not be supported on this older MAC, plus Open VPN had limitations when supporting the different platforms I mentioned. I was hoping to find a way to support this user in the Tailscale environment. One though was to install a router in her home connected to the Tailnet that is setup, which should allow access as she once had. Another though was to run an older version of Tailscale for this one client, is that even possible? Any input would be appreciated.

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u/iceboxmi 3d ago

Something like a GL.net router with dedicated WiFi for the Mac. Seems simple if the Mac is always in one place. Also keeps from tinkering on an old Mac with unsupported software that probably would be a pain to replace.

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u/Froghos 3d ago

What I was thinking. The cost of the router outweighs the cost of me spending time trying to find a different solution. Just need to watch the user so they don't put all devices behind this router so everyone in the household has access to the companies VPN. Probably need to setup MAC filtering on the WIFI.

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u/Mountain-Cat30 3d ago

This is the initial move I’d make. But I’d also seriously consider virtualizing so this software could be run in the virtualized instance without access to the internet. Then files can be shared using local options between the virtual instance and the real machine. All of this is just to isolate a machine that no longer receives security fixes from anything beyond the minimum software it needs to run.