Please, shut up and take my money — or how I am unable to pay Microsoft

I have been using a couple of Microsoft’s online services for a while — it is mostly OneDrive that made me chose them instead of other cloud providers. I started to use Windows Live Domains too so I can use Outlook.com with my own domain; it integrates nicely with other MS services, its UI is all right and its folders/categories paradigm plays nicely with 3rd party email clients (unlike GMail labels).

I do not like ads in the sidebar, and I am completely all right with paying for stuff I use on a daily basis so around 1.5 years ago I have decided to subscribe for ‘Ad-Free Outlook’. It is 20 euros a year which is reasonable, I pay twice as much for my Fastmail account. And then the problems started.

Whenever I clicked on ‘Upgrade to Ad-Free Outlook’, I was forwarded to some ancient-looking Windows Live site telling me that I need a valid Windows Live ID to complete this request. I obviously had a valid ID, that is what I had been using to log in to Outlook. Anyway, I figured this is probably caused by having a non @[outlook.com|live.com|hotmail.com] primary alias, therefore I created one on @outlook.com, and tried to set it as the primary one. Obviously it did not work. (‘Error completing request, please try later’, or something like that.) For months. After a couple of months I asked MS support to fix it for me. They did, it took them around 4 weeks and many-many emails, because I had been given the explanation that I have some kind of ‘false duplicate ID’ that needs to be deleted. And, wait, if that ID is deleted then any information associated with it is going to be deleted. I asked what info is that, and whether it means that the stuff on my OneDrive is going to be deleted — they kept repeating the same stuff over and over again about false IDs and deleting associated data.
After a while, I thought ‘screw it’, and gave them permission to delete that mythical false ID.

Nothing important got deleted in the end, I could set @outlook.com as my primary alias.

Today I tried to subscribe for Ad-Free Outlook again.

Well, this does not seem to work. And yes, it is recurring. Let’s click ‘Continue’.

Really? MSN Internet Access? Copyright 2007 Microsoft Corporation?

Let’s try and click on ‘Feedback’, maybe we can get some support.

So it thinks I have subscribed to Ad-Free Outlook and Dial-Up Internet Access and Premium Internet Software. Wow. Can I get support then?

No, I am not entitled to support for these services. Oh my. I think I should just go through the main support page at support.microsoft.com, they can surely help. Oh, and they have live chat! Let’s talk to Newa, he seems to be available and has 5 stars rating. Click…

So they can’t complete the request because of an error.

It seems today I won’t be able to pay Microsoft. Again.