Sometimes the path we choose is only met with minimal speed bumps. We’ll call that a good day. Spoiler alert, MS DNS doesn’t play nice. Who’da thunk it? 👎 What, no middle finger emoji? I am appalled, Windows 10.

So, you’ve been putting it off for a real long time, maybe you got sidetracked reading r/ShittySysadmin on Reddit, and you haven’t felt like dicking with it, but today’s a new day, and you haven’t totally had your fill of punishment yet, so you decide to take the plunge.

For a little back story, after almost twenty years of being a sysadmin, dealing with endless server problems, Windows problems galore, buggy software, and providing direct tech support to crabby, ungrateful end-users, I’ve recently come to the conclusion that to be a sysadmin, whether you know it or not, you have to be a masochist deep down, because only a crazy man would willingly endure this kind of torture. Smh. It’s true, it’s true. 🙄 Anywho, I’ll be your copilot this evening, so let’s kick this bitch into overdrive, and get some shit done.

Here’s some basic instructions to implement DKIM signing on Microsoft Exchange 2019 CU11 relatively painlessly in about 15 minutos, pending you’re on a recent version of Windows. In my case, I was on Windows Server Standard 2019 LTS v1809, so no .NET dependencies needed to be met. Cue Ranier Wolfcastle, “Up and at them!“.

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