A Microsoft Nightmare

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About a month ago I started on a journey that ended up being one of the most frustrating tech issue I think I have ever dealt with. I've been doing this for close to twenty years now, so it isn't like I am some kind of noob just getting my feet under me.

It all started due to some consulting that I was doing on the side of my full time job. I help a small municipality out with some of their tech stuff from time to time and they were in desperate need of some changes.

The primary issue being that for the past several years they have been using @yahoo addresses as their main email accounts for the city. No matter how big or small, in my opinion it is a huge issue to be conducting official business over a commercial email account like @gmail, @yahoo, @hotmail, etc. First, it just looks tacky, but second there are the inherent security issues that come with using one of those types of accounts.

I had been pointing this out to them for years, but it was only recently that some people came on board that were willing to spend the money to make change happen.


The city had already applied for a .gov domain some time ago, so most of the legwork on that was all taken care of. Once the application for the domain was set, the first issue was getting it registered. This actually has nothing to do with Microsoft, but it was frustrating none the less. Since the city doesn't have their own DNS servers, we had to find someone to host the DNS so that the .gov registrar could verify the domain. Their support was less than helpful when it came to directing me to a vendor that would do .gov hosting. I finally found a local vendor who I have worked with in the past and I think ultimately it will be a good fit for the city.


Then came the real headaches....


My plan had been to get the city setup on the Office 365 platform so they could have their .gov domain emails setup through that. It would also give them access to Office 365 Online so they could have and use the latest versions of Office. I think they were still using Office 2010 or 2013 and were in desperate need of an upgrade.

I got the products ordered for them only to find out that Microsoft wouldn't allow us to process the order without an email address. That isn't too surprising, but it soon became a chicken and egg type scenario in that we needed the order processed to setup our email addresses, but we couldn't process the order without the email address. Of course Microsoft would not allow you to process the order with a @yahoo or @gmail, etc email address.

I eventually got a work around using an email address from my full time employer. In retrospect, that was a mistake and I wish I could go back and change that, but it is done now.


With the order processed, I thought things should be good to go.

Unfortunately, once again that wasn't the case.

To get things setup you also needed an email address on the domain. We were immediately hit once again with the chicken and egg problem. I spent several hours over several days on the phone with Microsoft trying to explain that to them. It was maddening. Finally, I found someone that got us setup with a .onmicrosoft.com domain to at least get things setup and then we were able to go in and add the .gov domain to the mix. After some DNS record changes things were finally flowing through properly .

It only took about 2 months longer than it should have!

Here are my two key takeaways from this whole thing:

  • Have a plan for email ahead of time. Even if you are just hosting it on a third party provider until you can get it moved over to Microsoft, have it setup ahead of time. At the very least, have a random domain and email address that you can use as a temporary "staging" account. Preferably not one on the production domain of another company.

  • Make sure you have full access to the domain accounts and servers required. Because we had to work with the third party host the DNS, it became tedious waiting for them to add the appropriate records and make changes to test everything out. With full access on my part the final part probably could have been done in an hour. Since I had to relay the changes to the other company and wait for them to make them it actually took about two days.

Needless to say, I am extremely happy to have this portion of the project behind me. Now I just need to get the handful of accounts set up for them and start them down the road of what will hopefully be a more professional productive user experience!


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11 comments
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Encountered this issue when migrating customer email from @gmail to 0365 email. Didn't expect the extra step. Luckily all migration are done successfully

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That is great to hear! I am glad you were able to get it sorted out. Google was on my shortlist, but the cost was more expensive for them. I am just glad this nightmare is behind me and they can start enjoying the benefits!

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Do you know how much it cost the city to buy the licenses?

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It was just under $1000 per year for ten licenses.

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Sounds reasonable, but I guess that is an annual subscription rate.

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Yeah, that is for the Office 365 thing.

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I think that this migration should be easy and hassle-free and since Microsoft is involved so we can expect better but things were not easy for you.

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Thatñs why I hate workarounds, if you don't fix the root cause from the start but work with bandages your project will end up smelling bad, like festering wounds. but nice read !CTP thanks

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Thanks for sharing your experience! It's a wonder they are so profitable.

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After 40+ years in the computer industry, believe me, I understand your frustration. I think it has gotten worse since we are moving away from mainframes.

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