Spam filters are notoriously tricky for everyone, not just microsoft.

Bullshit, it doesn’t block a damn thing for me ever lol

My wife and I have both used gmail for twenty years - she's been sending me email from her account for years, with my personal domain forwarding to my gmail. But since the Google Domains > Squarespace disaster, the gmail spam filter has lost the plot - it will occasionally spam filter of her from-gmail emails mid thread.

I am certain I have missed critical emails because of this, so trust is gone. I now have to dedicate time each day to going through my gets-an-email-every-two-minutes spam folder. Even though I happily worked there for 16 years, I sadly now find myself in the process of de-Googling.

Oh yeah... every day half the mail I receive at work is flagged as "unsafe," and then the banner that tells you this in Outlook presents a button to "manage safe senders."

So I press it and add (for example) OUR OWN JIRA SERVER to the whitelist... which HAS NO EFFECT. Every goddamned day, every Jira message is flagged as dangerous and has blocked content.

I complained to Microsoft, who made up some pathetic excuse about how that's not what that button does... and how every person at my company should contact OUR IT department to have the senders of every E-mail they receive added to some OTHER whitelist, one at a time. Seriously.

The stupidity level at Microsoft today isn't funny. It's sickening. It's also offensive, wasting paying customers' time to the tune of thousands of man-hours daily (and that's probably just at my company).