The Gmail honeymoon is over

I work for IronPort, so I know a little about anti-spam. I also used to self-host all my email on leased Linux server, so I understand very well the volume of spam out there and just how well one can tune an anti-spam system (I used SpamAssassin) to get good results. I recently stopped running my own server because it was too expensive, so I switched my MX records to hosted Gmail and I really do like it. For the most part, it’s been great.

But today I noticed a horrifying false-positive (FP) problem. In the anti-spam world, an FP is your worst enemy: it’s the unlucky event when you mis-classify a normal email as spam. On Gmail, that means an email I actually wanted to get ended up in the “Spam” folder. That can be bad, and in some cases, catastrophic.

I got concerned when a friend of mine told me that a conversation between a few of us (all Gmail users, both hosted and regular) ended up in his Spam folder. I was appalled, and then worried. If a conversation about getting together and buying tickets for a concert got buried, what else might be going awry? It turns out, a lot. Here’s some of the legitimate email I found in my Spam folder:

What the hell, Google?  That’s a terrible FP record and a really broad list of categories to screw up, and that’s just over the last 30 days.  Please do better.