Could Not Upload Certificate To Azure – AKA Lessons in Swearing

I’m doing to test work in the lab with Microsoft Azure at the moment, trying to tell which part of Microsoft is telling the truth about certain aspects of pricing. A necessary step in my tests was to upload an administrative certificate. I used MAKECERT to create the cert. The private cert is in Personal on the server that I’m working with. The public cert was on my PC. I opened the Azure portal and attempted to Manage Certificate to upload the .CER file but this failed after about 5 seconds. Recreate the cert, try again, fail again. No joy.

Then after I taught some of my Eastern European colleagues some new ways to swear in English, I had a realization that some dev in Microsoft probably did something dumb.

I bet they expect the private cert to be installed on the machine that you’re uploading the cert from … because we all browse from our servers, right? (WRONG, I hope).

So I exported the PFX to my PC, imported the cert, and attempted the upload again. And it finally worked.

Dumb. I can imagine “private” certs flying all around the network, and admins browsing from servers if this isn’t fixed by Microsoft.

On the bright side, my colleagues now are equipped with the verbiage to accompany flipping off your PC with the double bird.

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