Working with Microsoft 365 is never dull. Some days you’re the hero, other days you’re just trying to convince Outlook not to implode. Here are the usual suspects I’ve battled, with a few rants along the way.

Outlook: Diva Mode Activated

• Sent Items gone rogue: Send from a shared mailbox, and boom, it lands in your Sent Items instead of the shared folder. Because why not?

• Alias invisibility: Add an additional email alias and… nothing. It just refuses to show in the “From” field. Schrödinger’s email address: it exists and doesn’t, all at once.

• MFA login loop: Enrolling feels like Groundhog Day. Enter details, authenticate, get sent back to the start. Repeat until rage sets in.

• Install chaos: Installing apps from the portal? Not if an old trial or Office version is squatting on the machine. Then it’s uninstall/reinstall limbo.

• EXO adventures: PowerShell to the rescue… after you’ve typed, retyped, and typo’d the command about 14 times.

Licensing: The Support Gauntlet

Basic, Standard, Premium. Sounds simple until you actually need more. Cue my personal nightmare: trying to add additional licenses. Support dragged me through every hoop imaginable: assignments, billing checks, provisioning resets, the whole nine yards. And in the end? Not my config, not my setup… just a backend server issue. Nothing like wasting half a day proving the problem isn’t you.

Admin Portal: The Wizard’s Lair (But I’ve Got the Map)

The Admin Portal gets a bad rap for being a maze of endless menus and toggles. Sure, one wrong click in Conditional Access can lock everyone out, and security defaults sometimes trip over productivity. But once you know your way around, it’s less a labyrinth and more a toolkit.

My go-to moves:

• Document every change so there are no surprises later.

• Test policies with a dummy account before rolling them out.

• And yes, skip the menu-hunting. Google the exact setting name and go straight there. Efficiency over wandering.

Bottom Line

Solutions are often hiding in plain sight. The real enemy isn’t Outlook, licensing, or the Admin Portal. It’s overthinking (and maybe the occasional server tantrum). Keep it simple, keep it sharp, and you just might get through the day without throwing Outlook out the window.