Ditching Technical Debt. Embracing Simplicity.

I work in networking. I’ve been doing that for a long time now. Along that journey, I’ve also had occasional detours into worlds like generic IT and data security as well. I also do volunteer work at a nonprofit. Plus, like many of you who work in tech, there’s stuff that lives at the home(s) of relatives that you maintain because you’re that sort of person.

Sometimes, you do it cheap, sometimes you do it right, and sometimes you do it somewhere in-between. Like where you’ve got DHCP-assigned WAN interfaces everywhere because everywhere has home-user type Internet services, or less-expensive business-class occasionally. Anyhow, you can’t always count on having the same IP in the same place twice. BUT, you want things to be secured, and you don’t just want wide-open port forwards with plain old Dynamic DNS.

How things used to work, in the IPsec days…

You’ve got some Juniper SRX firewalls you’ve bought for lab work & study previously, you want to make use of them with IPsec VPNs, but to do it right, you really need static IPs. So, what do you do? You fake it. You just pretend you’ve got static IPs on the tunnel endpoints and configure it up. The tunnels come up, you post up your BGP sessions between your st0.0 IFLs, announce some routes, put some reasonable security policies in place. Yes, I did have security policies in there. I was born at night, but it wasn’t last night, guys. But how did I keep it working with IPs changing all the time?

Here’s how I was solving that problem up until fairly recently. I’ve been hacking away at my DNS-o-Matic and DNS Made Easy updaters for a while now. The DME updater was much better, IMHO, as it directly updated a single, private zone that only I ever cared about rather than rely on someone else to sit in the middle and do the updates for me. Plus, I wrote the whole thing from the ground up using DME’s API docs, so I knew exactly how it worked, inside & out. No excuses for it doing anything I didn’t understand, and honestly, I’m really happy with how well it’s been working. It’s been a great opportunity to get better at Python, in particular doing things in a more “Pythonic” way, rather than trying to “just get it done”, or worse, trying to make it work the way I used to do things in Perl or PHP years ago. Is it iconic? Not even close, but it does works pretty darn well.

So, with these containers all ran on Intel NUCs under Ubuntu Linux at each site. There were 1 more container on each of these NUCs as part of this operation. I had a set of Telegram Bots that talked to each other as part of this network to inform each other of site IP changes. So, if HOME changed its IP, the bot at HOME sent a message to the group that included the bots for NONPROFIT and INLAWS. Those bots saw note that the IP had changed and they should go find out the new IP of HOME, so they can update their tunnel endpoints. This in turn fired off a function that used the Junos PyEZ API module to update the IPsec tunnel endpoint IPs.

Did it all work? Yes, believe it or not, this actually all worked. Was it pretty fragile and not for the faint of heart? Oh yeah, for sure. Would I recommend doing it? Not a chance. So much so that I’m not even going to share the code, apart from the DDNS updaters. The other stuff is definitely hackjob territory. So, since it was so fragile and had the tendency to break, what did I do? Well, the first few times, I drove and fixed. Which frankly, sucked. After that, I installed an OpenVPN container at each of the locations. Later, I replaced those with linuxserver/wireguard containers. But, after it all broke like twice in about a month, I’d just about had enough. I cried Uncle and decided I was going to look for some other way to do this.

And that’s when my old pal Bhupen mentioned Tailscale to me. I was already into Wireguard. So making it easier, faster, and more useful were all on my short list. Drop the tailscale client on the NUC, get it logged in announcing the local subnet into the tailnet (their name for the VPN instance), making it a “subnet router”, approve the route announcement in the portal and it’s going. I’ve got control over key expiry too. Security policy (naturally) moved from the SRX down to the tailscale gateways, but their ACL language wasn’t too difficult to wrangle. It’s all JSON, so it’s reasonably straightforward.

The new Tailscale VPNs
The new Tailscale VPNs

So, with all the scripts gone and the IPsec stripped away, what’s it all look like? Well, we also added 1 more site into the mix as well – the in-laws vacation place. They bought a place and I stuck a Raspberry Pi up there for future IOT use. Not entirely sure about the “what” yet, but they just updated the HVAC, and it’s all smart stuff, so I expect there will be instrumentation. Maybe something that spits out time series info to Influxdb or somesuch. Who knows? Or Perhaps HomeKit/Homebridge stuff. Time will tell.

In the time since I made the diagrams and wrote this up, things have also changed slightly on the homefront.. I’ve deployed a 2nd subnet router at Home. In the Tailscale docs, they say all over the place not to deploy two subnet routers with the same IP space, and generally speaking, it’s with good reason – traffic destined for those prefixes announced by those routers will be round-robin’d back and forth between them. In my case, since they’re on the same physical subnet, this is essentially ECMP routing, so no big deal. I haven’t validated if they’re really getting the hashing correct, but haven’t really noticed any ill effects yet, so I haven’t shut off the 2nd subnet router yet.

So, by dropping all the BGP sessions, IPsec tunnels, Python scripts, Telegram bots, and Docker containers, things have become much simpler, and much more stable. I’m really happy with Tailscale. So much so that I ended up subscribing at the Personal Pro tier. Great bunch of folks – can’t help but recommend them.

UPDATE: This ended up sparking a bunch of sidebar conversations. Go read what I had to say as a followup

Author: jason

Husband & Dad. Mover of packets. Automator of things. Lover of dogs. Occasional coder of Python and builder of containers. All around geek.

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