Microsoft – The Worst Tech Support Experience Ever

Okay let me start with a few disclaimers.

#1. I know this is a “first world problem”. I live in the first world. So yeah.

#2. I’m a former Microsoft employee but this has NOTHING to do with ex-employee griping (which is how many Microsoft employees like to write things off).

#3. Don’t tell me “you shouldn’t use Office, you should use iWork / OpenOffice / LibreOffice / Google Docs and just import/export”. Bullshit. I’ve tried them all and the import/export stuff is still broken. Fonts go missing, images move, and when you work (as I do) in MARKETING, writing and editing client documents, FORMATTING MATTERS. Do you think I pay Microsoft because I hate my money? NO.

#4. I don’t expect anyone at Microsoft to give a shit, but I’m writing this JUST IN CASE THEY DO.


Right. So. Rant done. Well… that part of the rant, anyway. Let’s get onto the REAL rant.

I just wasted an entire day of work thanks to Microsoft “tech support” (and I used that term loosely). 

Here’s how it went down.

I turned on my Macbook Pro (2010 model, not that it matters) and it told me I needed to update Microsoft Office to 14.3.9. Fine. So I let it download and tried to install it. FAIL. So I manually downloaded the update pack and tried again. FAIL #2. Re-boot the Mac. Try again. FAIL #3.

So… and here’s where I made a mistake – I LOGGED A MICROSOFT SUPPORT CALL.

A nice lady with a delightful accent (whose name I will leave out) offered to log into my machine via LogMeIn and sort it out for me. Great. She tried to install the pack and, again, it failed. She spent another couple of hours trying to make it work AND IT STILL FAILED.

Okay, now this is the good bit. She advised that she would have to un-install Office and re-install it. ARE YOU KIDDING?? Sigh. Okay.

So… an hour to download a 1GB .dmg. Then she installs it. Then she tries to install the update. Oh, but wait – she has to install TWO updates – because the .dmg doesn’t include them. THEY FAIL.

Finally – and by this stage it’s about 1pm (and this has taken up my entire day because she is using my laptop) – I say “THAT’S ENOUGH! I’ll just use the old version of Office because I have work to do.” Then I open Powerpoint and… it won’t open. It’s borked. I can’t even sign in because it’s asking me for a product key and I don’t have one because I bought the Office 365 licence (where you pay by the month or something). I ask the lady “how do I get a product key?” She says she has to install the updates before I can login with my email address. BUT THE UPDATES DON’T WORK, I say. Yes, she says, I know, so I need to keep working on it.

Resigned to this, I agree to let her keep working on it.

TWO HOURS LATER – this is about 3pm, mind you – I look at my laptop and notice nothing is happening (I’ve been talking to her in a chat window). I type “hello?”. Nothing. Nada. Zip.

So I ring the Microsoft support help line, wade through the options, talk to someone, explain the situation, she puts me on hold for a few minutes… and then comes on to tell me this:

“Oh they cannot help you at this time because their support tools are being updated. They will have to call you back in an hour.” 

I ask… befuddled.. “Why would she choose to update her support tools IN THE MIDDLE OF A SUPPORT CALL?”

“Well it’s not her, it’s an automated update, it’s out of her control”, I am informed.

I SHIT YOU NOT, ladies and gentlemen.

BUT WAIT – there’s more.

I wait for an hour. No phone call.

Then I say “fuck it” and look over what she had done to my laptop. I notice that the version of Office she downloaded for the fresh install seemed to be the WRONG VERSION OF OFFICE. She downloaded and installed the standard version – NOT THE 365 VERSION. Which, of course, is why it was asking for a product key.

So I go to, log in, download ANOTHER 1GB file, install – and PRESTO, I have Office back! I can work again!


PS – Tech Support don’t know that I’ve fixed it and they STILL haven’t called me back after updating their “support tools”.

PPS – This time I’m not going to bother with Microsoft’s “critical update” 14.3.9″. Fuck it. I’ll take the risks until I have another day to waste.


4 thoughts on “Microsoft – The Worst Tech Support Experience Ever

  1. I just wasted a day with MS support as well. I purchased a Win7 Pro from Toshiba (could not use Win8 for various reasons) and needed BitLocker so called Toshiba who said they cannot sell Ultimate. I purchased Ultimate online from and used the product key which worked for a few weeks. Then I get the Genuine message, blah blah, and called Microsoft. They said it was a PIRATED copy so I asked my options, which was to pay them $99 and they could generate a product key and contest the charge on my credit card from I seriously spent six hours, went through seven techs each telling the story from the beginning, and getting dropped or sent to the wrong place 10 times. I spent $99 for tech support and when they could not fix the issue wanted to refund the money. I said that did me no good because I have a laptop that is less than functional and they needed to escalate. Everyone said they are sorry and understood but ultimately NO ONE could resolve a simple licensing product key issue and sure enough while waiting on hold for the last person who PROMISED would get me a resolution I heard the dreaded dial tone. MS has the most dysfunctional support group I have EVER worked with in my life and that includes the carriers.

  2. Worst employees ever, they will want to do this steps the first minute they come online:

    First, greet you and immediately redirect to you to technical ASAP and walk away from the problems you have and technical simply doesn’t bother with picking calls either. so in a nutshell, they’re comfortably paid and not dealing with shit because it your problem for getting the product working on you pc not theirs.

  3. Wow!!! Almost same story. Bought 365 and tried to download…fail and so on. Got support and she said she would take care of problem. Fail for more times than I care to count. She needs to transfer my problem to higher level support. For abou three days nothing but fail so my high level tech decided it was my Win 7 problem and she starts cleaning that up. Ultimately she has to reinstall Win 7 Ultimate and then Office 365. Down 1 week but she did finally get it running (Win 7 and Office). That was in 2013. I now must install on new system as my old one is giving up the ghost. OK I need the key but since I bought from the store they emailed it and I have since lost it. I went on line to get help with the key for my Win 7. When I did it said it could not verify my Windows as genuine. Are you kidding me? I have everything except a support person to help me thru this so now I am again having to beg them for help or buy another copy. BTW the folks I did reach took all my info and put me on hold. Make that eternal hold since I eventually was switch to the phone menu and have not heard one word from anyone at Microsoft. Next stop is a Microsoft Store so I can look them in the eye when they blow me off.

  4. I have had problems with windows 10 rev 1803 from when it was installed on my computer without my approval. I have constant problems now with audio and videao bit nobaody can sove the problem. one of the level 2 speacilist did not have a solution

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