My sorry tale of trying and failing to buy a Visual Studio cloud subscription

UPDATE: this story now has a happy ending – a bunch of awesome Microsoft people helped me activate my subscription so I could get up and running.

Let me start off by saying this isn’t a rant against Microsoft in general, or me saying they suck, or that I hate them.

Microsoft don’t suck.

I don’t hate them.

They make some of the best products in the world: Windows 10 is great, Visual Studio is fantastic, SQL Server is awesome, Azure is likewise brilliant, and the Xbox is a staggering achievement, especially considering where Microsoft started out in games.

They’ve had a bit of a miserable time in the mobile market but at least nowadays Windows 10 Mobile is a decent product and I’m sure, if they play the long game as they usually do, they stand a decent chance of building a good business around mobile, just like they’ve done in gaming, and just like they’re doing with cloud.

So what is this? Simply an expression of extreme frustration at the overwhelming crappiness of a specific process: that of buying a Visual Studio subscription.

I feel a bit bad about posting it actually. I started out building this document as a way to keep track of everything I’d tried and to make it easier to explain to Microsoft’s support team what was going on, but after 28 hours and no progress I feel like I need to make my voice heard perhaps a little more loudly. I also really need everything written down where anyone who’s involved can see and understand what I’m seeing as I work through this process.

By the way, it’s not that people at Microsoft haven’t tried to help (see below), but none of it has worked. I still don’t have access to subscriber downloads and product keys, which is blocking at least some of my work.

Some Background

I used to work for a company called Red Gate, up until the end of 2013 – a fact that will become relevant later. Back in those days I did some work on Node Tools for Visual Studio, which I carried on into 2014. As a result of this Microsoft kindly gave me an MSDN subscription, which only recently expired.

After a few months of doing other things I now need to start working with Visual Studio and Windows again for some projects, along with upcoming speaking engagements over the next three months. I therefore need to buy a Visual Studio subscription.

I don’t mind paying at all, and here’s why: a Visual Studio cloud subscription costs $539/yr. Given it includes SQL Server, plus Windows operating systems for for dev and test environments, to me this represents excellent value for money.

So no big deal, or at least it shouldn’t be. You just visit, pay for a subscription, and you can download the products you need and crack on.

Reality Bites: The Purchase Process

I’m not enough of an idiot to try buying Visual Studio direct from Microsoft are a massive company with sprawling web properties, so I start out with a web search. It doesn’t matter whether you use Bing or Google, if you search for “buy visual studio” you pretty quickly end up at:

The page itself looks really promising, and there are links to a page that describes the benefits included with the standard and annual cloud subscriptions. From my perspective the important point is that I get access to all the Microsoft products I need to develop software, along with some free Azure hosting, which is great.

How to buy Visual Studio page.

Looking at this, it’s a pretty easy sell for me to go with the annual cloud subscription at $539/year because it includes everything I need at a lower TCO to the standard perpetual license.

So I click on the Buy now button for the annual subscription and end up at:

Visual Studio buy annual cloud subscription page.

This is marginally irritating to me because I’ve already said I want to buy the thing so I either want it in my shopping cart, or to be taken somewhere where I can pay for it, not to another page full of information I already know/don’t care about. I don’t need to be marketed to at this point.

Still, there’s an obvious Buy button, so I click that one too.

Now I end up at

(No, I’m not making that URL up.)

Visual Studio login page.

I briefly debate whether to create a new Microsoft account against my business email address (for which I’m the company owner) rather than reuse my existing account against my personal email address.

In the end I decide to create the new account, so I type in my business email address and, as expected, I get an error because I’ve never signed up for a Microsoft account using this address:

Expected error after using new email address so I can create a new Microsoft account.

Like I say, this is fine, because it gives me what a want: a way to create a new Microsoft account. Arguably this should have been an option on the previous screen but whatever – the main thing is I have a way to do it.

This is where things start to get ugly though, because when I click on “get a new Microsoft account” what happens is it opens a new tab pointed at the original login screen:

Visual Studio login page.

This was in Chrome. In Firefox it’s even worse: it opens up two new tabs, both on this page. I tried it in private browsing, in case Microsoft have banjaxed their cookies, but still no luck.

Much as I might want to, I can’t use IE or Edge because I’m running OSX. I’d need to create a Windows 10 VM via Parallels. Unfortunately I can’t do this because without the Visual Studio subscription I’m trying to buy (!), and I also unfortunately don’t have any old Windows 8.x VMs lying around that I could use for this purpose.

OK, well, no worries. I’ll just use my existing Microsoft account attached to my personal email address instead. I realise this is probably a better idea anyway because my website at is hosted in Azure and is tied to this account. I can just buy a new subscription and change the email address for my account, right?


So I enter the email address for the account I already have, against which the expired MSDN subscription is attached, and after a few seconds this redirects me to to log in:

(Again, no, I’m not kidding with that URL.) page to login to existing Microsoft account.

So I enter my password, select Keep me signed in, and click Sign in. It doesn’t work. I’m redirected and end up on a page at with the following error:

Basic login error after login attempt on

There’s some more detailed information at the bottom of the page:

More detailed login error information.

I try this several times with the same result. Suspecting cookies I switch from Chrome to Firefox, go through the same process, up to the login page, and try to log in again.

This time it works. I suspect it would also have worked if I’d used a private browsing window in Chrome. Clearly something about trying to create a new account hosed the cookies (I use ‘cookies’ in the loosest sense of the word – they could be using local storage on the client for all I know; I haven’t looked).

Now I’m at:

This is a page I’ve been on before, but now I have a popup that looks like it’s going to take me through the purchase process:

Popup to purchase Visual Studio subscription.

There are no other options in the dropdown so I hit Continue. This goes through a couple of redirects, lands back on the same page with a different URL (, says it’s checking my subscription, then gives me an error and greys out the Continue button:

Error saying I am not an admin or co-admin of the subscription.

(Later it becomes clear to me that this error is factually correct, if unhelpful. The Windows Azure MSDN – Visual Studio Ultimate item refers to an old, expired, MSDN subscription that I had through Red Gate. At this point I don’t realise this though.)

In desperation I click Create new Azure subscription but it takes me to a page on that doesn’t seem immediately relevant to what I’m doing because it’s talking about Pay-As-You-Go Azure subscriptions, whereas I want to buy a Visual Studio subscription, so I ignore it.

In passing I notice that Firefox has blocked Flash on the site and briefly wonder why the site uses Flash at all:

Firefox has blocked Flash on

Anyway, as I said, the page doesn’t seem relevant so I ignore it and move on. Later it will become apparent that this was a mistake and, I suppose, my bad.

Frustrated, I decide to log in to my Microsoft account from elsewhere, in a private browsing session, to see if I can figure out what’s going on.

I end up back at

Here I am, back at trying to log in again.

Eventually, via some tediously circuitous route that I’m unable to fully recollect, I end up at Oddly I note that there appear to be two profiles attached to my account, one named “Microsoft Account”, and the other named “Red Gate Software Ltd”. (Switching between these profiles involves 3 redirects taking around 4 seconds in total.)

The "Microsoft account" profile attached to my account.

The "Red Gate Software Ltd" profile attached to my account.

I have access only to Visual Studio Dev Essentials benefits (i.e., all the free stuff), but this isn’t surprising since I left Red Gate 3 years ago and, as I’ve already said, the MSDN subscription that Microsoft kindly gave me expired recently.

There’s nothing here that shows me definitively what the problem might be but I am a bit suspicious about this Red Gate Software Ltd profile. I’m at Red Gate for the day so I pay a visit to their Information Systems team to see if they have any insight into what’s happening. Not surprisingly, I’m no longer in the list of subscribers they manage, so no dice there.

In the end I call the relevant Microsoft UK support line on 0800 051 7215 and select option 3 for Visual Studio subscriptions.

I talk to a guy there, who’s name I didn’t get on this occasion, who after a few minutes on hold whilst he investigates tells me that I need to create a new Pay As You Go Azure subscription, then I’ll be able to attach my Visual Studio cloud subscription to that. There was a bit more to it than that because I didn’t immediately grasp what he was telling me to do or why, or where I had to go to do it. He gave me a number to call for Azure support who would be able to help me.

Not really wanting to waste any more time on the phone, I did a bit of googling, and ended up back where I was after I’d clicked Create a new Azure subscription above, only now I understood that this was the right place to be.

I went through the process of creating a new subscription, supplying new payment information along the way (my old payment method had long since expired), which went fairly smoothly and I ended up in the Azure portal, as expected, with all my stuff (most of it entirely uninteresting):

Successfully created an Azure Pay-As-You-Go subscription and logged in to Azure portal.

OK. So about an hour and a half has passed since I first tried to buy Visual Studio. Bear in mind that buying goods on Amazon takes me about 10 seconds once I’ve decided what to buy.

Now I go back through the process to buy Visual Studio for the third time, and end up back on this page again, only now my new Pay-As-You-Go subscription is showing up:

Now I can buy Visual Studio with my Pay-As-You-Go subscription.

This time when I click Continue the subscription check succeeds and I can go ahead and select a quantity, confirm my acceptance of the terms and conditions, and click Confirm. I get a message indicating that my purchase has been successful. (I don’t have screenshots of this because I can’t get back to this point – more below.)

This all looks good but I can’t immediately figure out how to download my software. When I go to the benefits section of my account, all I have are the essentials, and both the Subscriptions and Downloads sections of my account are still blank:

Blank subscriptions section in my profile after purchasing.

At this point I’m stumped so it’s time to call support again. I speak to a guy called Adam.

He tells me I should have received a welcome email. I check my email and discover that I haven’t received the expected email.

He also asks me to send him screenshots of my subscriptions area, and my area, which also shows nothing:

MSDN administration blank subscriptions area and error.

Adam’s a nice guy and he’s trying to be helpful. In fact everyone I’ve spoken to at Microsoft is nice and trying to be helpful; it’s just that I don’t think they’re really equipped to actually help. This is frustrating. By now about 2 hours have passed since I first tried to buy Visual Studio and I’m getting chippy. I don’t yell at or insult Adam, because it’s not his fault, but I do ask him to pass on some fairly blunt feedback about the purchase process to his manager.

Adam tells me there’s no record of my purchase and I should try again. However, now when I go back through the purchase process the button I need to click to make a purchase is greyed out and I can’t get any further:

Greyed out button that I'd previously used to make a purchase.

(Interestingly, and I hadn’t realized this at the time, this seems like the process I’d go through to add more subscriptions, since if I increase the quantity to 2 the Update button enables. Of course, that adds to the cost so I don’t go through with it because I don’t want to be billed for two subscriptions.)

He doesn’t know what to do about this so he needs to pass the details along to technical support and will get back to me. This is fine. I have a meeting, then I have lunch.

Roughly another two hours have passed and I’ve heard nothing back about my attempted purchase, and still no welcome email.

I call support again and end up talking to Adam again. I feel a bit sorry for him at this point because I’m really not happy by now and it’s really not his fault. He tells me that my enquiry will be dealt with. I’m sure that’s true but I ask him for a timescale because it’s now getting in the way of what I need to do in the afternoon. He says he’ll pursue it as soon as we’ve finished talking and get back to me.

About half an hour later I get an email from Adam (contact details redacted):


On 30 Aug 2016, at 15:03, [email protected] wrote:

Dear Bart,

Please be informed that your predicament needs further investigation.

I have forwarded your issue with greyed out button ‘update’ to our technical support.

Once there is a feedback in your case we will inform you accordingly.

My apologies for this inconvenience.

Thank you for cooperation and understanding in advance.

Kind Regards,



So basically I’m back where I was before with an enquiry forwarded to technical support but no progress.

For the hell of it I try buying again with a completely fresh private browsing session in Firefox but end up at the same roadblock.

I log in to Azure again and have a look at my subscriptions at because I’m wondering if the subscription I created on Azure even worked if my Visual Studio subscription purchase didn’t. Here’s what I see:

List of Azure subscriptions.

At the bottom you can see the old Windows Azure MSDN – Visual Studio Ultimate subscription, which is still active even though the associated MSDN subscription is long gone. (I’m not complaining, btw: it just strikes me as a bit odd.)

Then at the top there’s the new Pay-As-You-Go subscription I just created. If I click on the new subscription I see this:

Summary information for my Pay-As-You-Go subscription.

So, according to this I clearly have a Visual Studio annual cloud subscription, but there’s no record of it shown on It confirms my suspicion about the disabled Update button: it’s disabled because I’ve already bought one subscription and it’s not going to enable unless I want to add more subscriptions to what I already have.

Still, it doesn’t really help me because I can’t download Visual Studio 2015, SQL Server, or Windows 10. If I go to marketplace it shows I haven’t made any purchases, and if I go to downloads it’s all SDKs and command line tools for working with Azure. This stuff is cool and I’ll probably use some of it, but it’s not what I need right now.

Anyway, I go to the pub, go home, sleep, and by the time I’ve got up the next morning I’ve now heard directly from two different Microsoft employees kindly trying to help me out. I’m really grateful to both of these gentlemen – I think it’s great when people take the initiative to reach out and help:

John Montgomery and Buck Hodges of Microsoft see my plight on twitter and kindly reach out.

I go with Buck’s suggestion since, at this point, I’m blocked, I’m getting no progress elsewhere, and I’ll try anything to get some help. He’s asked me to open a free support case at

It’s worth pointing out that when I tried this first thing in the morning I got a 404 from the page where I had to select the problem type, but I tried again later – after a long meeting – and it seems to be working properly.

Cloud Services Assisted Support page suggested by Buck.

This seems pretty straightforward so I just click on Basic Support which, after a few redirects, takes me to

Choosing a problem type to create an incident.

I select Account Administration from the dropdown. This shows me a category list:

Incident category list.

Since I’m having trouble buying a Visual Studio subscription I select License assignment and purchasing. Now I get a section appear that allows me to contact Microsoft:

Now we get to start filing a support request.

I click Start request. This takes me to, and it’s here that I start to worry that something isn’t right.

Form to create an incident.

The problem is in the top right hand corner. Note the product name, which is Visual Studio Team Services Preview. This doesn’t seem right to me at all: all I’m interested in is getting access to the subscriber benefits for my Visual Studio cloud subscription, which to me sounds like a different product.

Worried I might be about to disappear down another irrelevant rabbit hole I start a new private browsing session and try to go through the same process but this time I log in to first. It makes no difference and I end up back in the same place, only it looks like it signed me out somewhere along the way. I decide to fill in the form anyway.

The last page of this form includes a severity rating, which serves only to aggravate me since I am entirely blocked on two separate projects because I can’t access my subscriber benefits and download Visual Studio:

The rather presumptuous severity rating.

Sure, from Microsoft’s perspective this might be “Severity C (Minimum business impact)” but not from mine, and who are they to make the decision about how much of a problem this really is? Remember that more than 24 hours has now elapsed since my initial purchase attempt.

At least on this occasion my submission is successful:

I've successfully submitted a support request.

In the meantime I hear from somebody called Michal at to say that they are still waiting on a response from the technical support department:


Dear Bart,

Thank you for your e-mail.

Let me kindly inform you that we are still waiting for response from the responsible department.

We will contact you as soon as any new information is available.

Kind Regards,



Yesterday I was also in touch with @MicrosoftUK on twitter, where a guy called Tom asked me to DM him to talk about MSDN admin subscriptions. Having done so I’ve now heard back and had a brief exchange with him via DM:

Twitter DM conversation with Tom on the MicrosoftUK account.

At this point you can probably tell I’m getting a bit frustrated again, albeit that I’m trying to be polite.

In case Tom’s on to something here I go back to Red Gate again and verify that they are not administering any current or past MSDN or Visual Studio subscriptions attached to my Microsoft account. They verify that this is the case – I do not appear in their subscriber management list, can’t be found via search, nor by any other means.

Where does all of this leave me?

Well, after 30+ hours of wrangling there appears to be nothing I can do except wait. As much as people are clearly trying to help I don’t feel like anyone I’ve dealt with so far is in a position to resolve the problem.

As a result, I’ve still got no Visual Studio download, let alone a working copy installed, nor any other software downloads or license keys available to me. As I’ve said, this now means I’m blocked on a couple of projects, which is frustrating and shortly likely to become extremely problematic.

Those of you with long memories might remember Bill Gates’ rant from 2003 about his experience of trying to purchase Moviemaker and the Digital Plus pack:

It’s not a terribly British turn of phrase but, as it echoes down the years, I can’t help but agree with him when he says, “I am quite disappointed at how Windows Usability has been going backwards and the program management groups don’t drive usability issues.”

Yeah, that pretty much sums it up. There isn’t one part of this process where something didn’t break, often in a way that blocked me completely or left me confused.

And, further on that point…

A few observations about my experience of using Microsoft’s various websites during this episode

Firstly, and most obviously, so much is broken. If you just go to read content you’ll probably be fine but the moment you want to interact with anything at all whether it works or not seems to be a complete crap-shoot. Compounding this, much of both what is and what isn’t broken seems confusing or non-obvious.

Microsoft sites use way too many redirects. I mean JUST WAY TOO MANY. So many actions result in three or four redirects back and forth between different properties. Not only does this slow everything down but it mostly breaks of the browser Back button functionality. This means if you do need to go back it’s often just easier, or your only option, to start the entire process again.

Microsoft websites are SLOW. Most pages take several seconds to load and, as already noted, the redirects really don’t help.

This isn’t universally true but usability and user experience overall is pretty poor. The next action you take often isn’t obvious. You end up just experimentally clicking around to find what you need. Moreover there’s very little consistency across sites. The broken functionality only serves to weaken an already poor experience in these cases.

Navigation in general is haphazard. For example, depending on how you go about getting there, if you want to manage your Azure account you might end up in the old Azure management console (with a prompt encouraging you to use the new portal), or you might go direct to the new portal. I still can’t figure out what I did to end up going down each different route but I can assure you it happened.

It’s really hard to find stuff. You end up having to use Google or Bing. Even then you might well end up with incorrect or irrelevant information. For example, if you search for “visual studio subscriber downloads” you get pushed towards the old MSDN Subscriber Downloads page. This is fine if what you have is an old but still live MSDN subscription. However, if you have a Visual Studio subscription you need to download from a different page, which doesn’t appear in the search results.

Really horrible errors are commonplace. Much of this seems to be due to extremely undisciplined use of cookies (or related client-side storage technologies). Sometimes these errors will appear in the page all nicely formatted even if they are pretty uninformative. Sometimes you’ll just get a raw response like this back from the server:

{"$id":"1","innerException":null,"message":"TF400898: An Internal Error Occurred. Activity Id: bc208830-44cd-435b-a79f-7e5e8db87730.","typeName":"System.FormatException, mscorlib","typeKey":"FormatException","errorCode":0,"eventId":0}

Indeed. A blob of incomprehensible JSON in my browser window. Classy.

In case you’re wondering, this came from

I feel like I’m being exposed to a sort of distorted external manifestation of Microsoft’s internal processes and architecture when I move between these sites and interact with their support teams. Whilst this is some mixture of interesting and infuriating, mostly the latter at this point, on a very basic level it’s not what I care about as a user: I just want to be able to buy, download, and use the software, and that’s it.

It’s not like everything is universally bad though. There are in fact many good individual bits:

  • Pages on the site seem on the whole simple, well-designed, and easy to use. Maybe there’s the odd extra click in there that you don’t need, but that’s nitpicking and it feels like, if the purchase process actually worked properly then it would be fairly simple to use.
  • There’s a lot of information in the new Azure portal but, on the whole, it’s well laid out and fairly easy to find your way around. I wasn’t even looking particularly hard and managed to find one setting that suddenly made my website fly (which I think was new over the old management portal). Honestly, even the old management portal was pretty good. I certainly never had any issues figuring out what I needed to do.

The problem is that as a whole the experience just kind of sucks because there are too many overcomplicated and apparently poorly tested dependencies between the different sites. The plumbing that joins everything together just doesn’t seem to work properly. There’s just way too much that’s brittle, or just doesn’t work under any circumstance (that I can realistically achieve).

Like I say, this isn’t a rant against Microsoft in general, just an account of the frustrations of trying to do one particular thing: buy and download some software. The fact that this is so difficult, well… from one of the world’s largest and most successful software companies it’s all rather unsatisfactory.

Maybe I’m doing something wrong, but it’s not clear what. Maybe there’s something wrong with my account. Again, it’s not clear what that might be.

I’ll update when I have more.

A final postcript

I just received another update from the support team that isn’t saying anything useful, other than somebody’s looking at the problem. Notably, no timescales:

Dear Bart,

Thank you for your e-mail in regards to subscription access.

Please be informed that I placed your case in our internal department hands.

As soon as they provide me with the feedback we will inform you accordingly.

I hope the above information is of assistance.

Should you have any further issues, please do not hesitate to contact us.



Update: A final postscript and a happy ending

I’m overjoyed to say that this tale, like all the best stories, has a happy ending. A group of fantastic people from Microsoft – notably John Montgomery, Buck Hodges, Marc Paine, and Andrew Brenner – kindly stepped in and helped me out.

They were able to provide a workaround to activate my subscription and are discussing solutions for the problems I encountered with a view to fixing them so nobody else runs into these problems.

Read the full story here.

4 thoughts on “My sorry tale of trying and failing to buy a Visual Studio cloud subscription

  1. Tony


    Wanting to know more about it, I googled visual studio cloud subscription and got to this.

    After reading this, Microsoft should make it up by giving you subscription for free.

    Thank you for documenting your experience. I hope some at Microsoft can take note and make improvements.

  2. Haakon Poulsen

    Bart, your tale of woe encapsulated in a nice package of, “come-on guys, I love your software and am happy to purchase it, can we possibly work together to get what we both want?” and then not getting the desired result at every turn seems to capture my experience. I too had a legacy MSDN subscription and account from an old employer and have since started my own business where I development software and model for my clients. “Sure, I’ll just get a new MSDN subscription” so that I can use any of my favorite software (SQL Server+Red Gate, Visual Studio, Visio, Windows+Server, Office) to get the job done. A similar rats nest of redirects, duplicate or conflicting pages (MSDN vs new Visual Studio Subscription vs Microsoft Account/Live) from multiple accounts, and the overall lack of transparency around the process and product offering really left a poor taste in my mouth. I also talked to a few agents who didn’t know what MSDN was or how to compare it to Visual Studio Subscription, and were helpful in giving me what information they could (which was ultimately not what I needed). After purchasing it and trying to download the software, I found my expectations dashed again when I found the software and versions I was looking for were not available (or I simply couldn’t find where to download them using their Visual Studio portal). I ended up calling and requesting a refund from the professional subscription, and will be stripping the keys from old computers/servers for a bit until this whole thing gets cleaned up (as I write this I can already see the made massive changes to their site and offerings page). So maybe a few more iterations, and then I can’t wait to give them my money and use their new software/services!

    Thanks for sharing, it was a great read and thorough.


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