[e12e]

I've been running my own (personal) email for a while now. And for a while, both hotmail/outlook.com and gmail have been eating my mail. Google is enough of an asshole to not report anything to the sending smtp, while outlook.com/hotmail at least gives you an error, so you know they got the mail all right, just didn't like your sending ip.

My ip/domain name was in no (public) black lists, however - when I finally set up SPF google stopped black-holing my email.

After I managed to get hold of admins of outlook.com via (I think, there were a few redundant hoops I jumped through):

https://support.microsoft.com/en-us/getsupport?oaspworkflow=...

Outlook.com/hotmail.com provisionally started accepting my email again. All this without my domain sending any spam the past few years.

Personally I think SPF is rather silly, but apparently it's considered an important filter-knob by certain services. I'd much rather gmail/outlook require valid certificates for smtp, and turn of plain-text, than all these add-on protocols that are supposed to avoid "forged sender"-type stuff.

Then I'd have to move over from cacert to a "real" cert, but hopefully that bar will be easier to clear once letsencrypt is up and running.