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O365 : Day 1

Posted in Blog, Computers, and Work

Overall the first day post-transition from Google to Office 365 for my company was less painful than I expected, which means it was only a 12 hour day…

The lion’s share of the issues were with the marketing department; they are a collection of bad computer habits coated in thick layers of change resistance, impatience, and self-importance.

For example, the marketing director (who has always been ~70% of the I.T. Department support time), managed to totally wreck his 2FA setup by being impatient and pressing buttons. Fixing this required completely removing his account and starting over before we could proceed with the rest of the company.

This was followed by him being convinced the O365 migration was causing his web-based Gmail address population to take 5 seconds longer than normal… It was actually some browser plugin skimming every email he wrote, and once removed the problem went away.

Yes, he’s Captain Plugin and is probably the source of this ancient meme:

Then there was the auto-BCC thing that he needs because the sent items folder is too complicated. See, he has this thing where he BCCs himself so that emails he sends show up in the inbox, where he then files them accordingly… So there’s a copy in the sent items folder and a copy in his archives – which is why he has 130,000 emails in his account. Microsoft figures (justly) that this is stupid, so it’s not an option – until I create a custom mail-flow rule to do this just for him.

Of course, while I’m working on this, his impatience strikes again and he decides to try and create some weird forwarding thing and winds up setting some address that doesn’t exist as his reply-to… And I start getting emails from employees with the bounce messages when they CC him.

So I get him to undo whatever it is he did, get his BCC working, and think that’s the end of the day…

Nope – then he tries to load the OneDrive app on some local machine where he’s managed to break the ‘work and school’ account setup. So the OneDrive app gives him a nice, cryptic Microsoft error and he pops back up in my email at 5:30pm…

Comparatively, the nice admin lady sending me an email at 7am stating she didn’t have any of her Gmail emails in O365 – which turned out to be confusion over the fact that the www.office.com page isn’t Outlook – was simply comical.

Oh, and there was one account that still had some residual local Exchange data in it, so O365 hung at “creating a mailbox” again… At least I’d already figured that one out a couple weeks ago.

Probably the biggest ‘issue’ was one of the test teams using + addressing at Google for testing (and not telling me about it), but + addressing is still experimental at Microsoft and isn’t enabled. Enabling it involved a lot of fiddling under the hood of MacOS to get Powershell running so that I could fiddle under the hood of Exchange, but I got that working too.

And, to celebrate, I ordered a pizza, am currently sitting in my darkened office listening to Porcupine Tree, and having a big bowl of mellow. 🙂

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