Resolving brief L2TP VPN sessions and disconnect errors

I recently abandoned macOS as a server solution (future blog post about that BS) and have switched to Ubuntu. The straw that broke the camels back for me was a reliable VPN solution that didn’t involve OpenVPN.

Don’t get me wrong, OpenVPN is fine, but the lack of built-in support for macOS, iOS, and iPadOS clients and having to rely on clunky or expensive client packages for support felt like a non-starter for me.

Instead, I wanted a simple L2TP or IKEv2 VPN. Virtually every OS has built-in client support for them and they’re plenty secure. Plus, it’s very easy to deploy to Apple devices using a .mobileConfig file.

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Apple puts macOS Server On the Chopping Block

macOS Server Icon

Lost yesterday in the flurry of software updates that included iOS 11.3, macOS 10.13.4, watchOS 4.3, and tvOS 11.3, followed by the disappointment of iCloud messages and Airplay 2 once again being pulled last minute from the public release, Apple pushed an update for their server package (5.6) that warns users of a big change coming in the Fall of 2018.

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Multiple SSL Websites in macOS Server

macOS Server Icon

Update: As of macOS 10.14 Mojave, macOS Server has been gutted and no longer include websites. This guide only applies to versions of macOS Server prior to macOS 10.14 Mojave.

Apple’s Server app can make basic sysadmin functions really simple for a novice webmaster. It can also make managing multiple websites, specifically multiple SSL websites, a nightmare.

I’m a firm believer that everyone should be using HTTPS for all their websites even if they do not use eCommerce. You don’t see me selling anything on this website (at least, not at the time of this post), but yet you’ll find that your browser is displaying a lock next to “” up above. It’s just the smart, safe thing to do, and thanks to the folks at Let’s Encrypt, you can have all the safety and security that comes with HTTPS for $0.00.

This isn’t the place to debate the merits of using macOS Server over virtually any Linux distro or Windows Server. This is for the green sysadmin-in-training with a Mac and nothing else who just wants a secure website (or four).

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