We currently have problem to send notifications and password reminders to Hotmail

We currently have a problem with sending outgoing emails to hotmail accounts. :confused:

I will continue to troubleshoot it tomorrow.

Hotmail still exists?

Yes. Yes it does.

It sure does, and the problem to send messages to Hotmail account is apparently because they are more draconic in spam prevention. We were blacklisted because enough people have clicked notifications from us as junk, while not enough have clicked "what, it is not junk". I have just registered in their spam prevention group/service/thingie, so I can see what kind of messages are reported to Hotmail.

I assume it is one or more of these scenarios (from the least likely scenario, to the most likely):
1. The spammers have found a security breach in the underlying infrastructure, so reporting it is junk is the only option (the least likely scenario).
2. The spammers have registered accounts here, and are using functions triggering notifications, and when receiving the notification the recipient click "junk" instead of using the report to moderator functions in here.
3. It is currently active members discarding valid messages from the site by clicking "junk", instead of updating their own settings.
4. It is former members discarding valid messages as junk, instead of logging back in to update their sittings.

Regardless if it is out of ignorance of the consequences to the site, or if it is out of malice, I will have to start dealing with the junk reports as an attacks against the forum.

Given the 15-year-old nature of both hotmail and this site, number four seems the most likely.

My guess is that at least 80% of the junk reports is from people being annoyed by getting a happy birthday wish from a forum they haven't visited for ten years.

At least, removing date/month should take care of that, birthdays tend to be spread around the year. So, if that is the case, it won't be a flood of report notifications at once. :)

The easiest solution is probably just to purge all the hotmail email addresses from the member list.

Nah... That's just the second easiest solution. But both of those would go against my pride as a technician. :)

Actually, thinking of it, it would be just the third easiest. Hotmail don't seem to share their blacklist, so doing absolutely nothing would achieve the same thing as if I replaced all the hotmail addresses with some random garble.

Looks like I finally have found the reasons of why Hotmail tend to blacklist us.

Apparently, it has been on these two reasons:
1. The SPF-records wasn't properly set up (but they are now).
2. The low amount of activity on the site means that we don't generate that many emails, while the "happy birthday"-function sends out emails to a lot of addresses that doesn't exist anymore (1-2 fails per day). Having a high ratio of sending to non-existing mail-boxes is a spam-like behavior.

There are two options to solve point two:
A. Delete all email accounts for those that haven't logged in for a few years (which would also block them from coming back, if they don't remember their password)
B. Start posting so there will be some valid emails going out, which would improve that ration :)