Microsoft Outlook thinks Microsoft Azure emails are spam

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).

I have several Google accounts registered at various emails, but they get auto-forwarded to my gmail. Gmail spam filter regularly puts Google's own messages related to those accounts into spam. I have marked them as "not spam" for ages, but the spam filter does not really learn.

No idea whether it is incompetence or malice, asking me not to use other email providers, too.

Use to maintain a couple of mailservers for an ecommerce platform. The amount of times we where greylisted by MS was so often. They actually have good tools at MS to check is your are blacklisted, but the greylisting was horrible. Resolution was always to request to be un-blacklisted at live, hotmail, and outlook. Never confirmation you actually where blocked, but problem was always fixed in half a day after that.

Who builds the gold-standard spam filter?

I run Gmail at work and Outlook at home and am thoroughly disappointed by both.

Looks like it is still not "fixed"; as it also flagged a couple of months ago for me: https://news.ycombinator.com/item?id=45604447

I suspect providers are tinkering with antispam systems, likely adding "AI". FastMail had good one for years, if not the best, was the last to make its antispam totally useless in last year or two.

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

Well, we're talking about something that makes all other mail readers draw J for smileys since decades because M$ doesn't give a shit about even de-facto standards, after all...

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