[TonyTrapp]

Similar question as my sibling comments. I have rented a server with a static IP address for over ten years now. Nobody else has used this IP during this time. Yet, every few months I have to beg Microsoft to unblock the IP. In the beginning I could do this on my own, but something changed a few years ago and now I have to beg my ISP (netcup) instead to contact Microsoft on behalf of me to temporarily whitelist the domain. Then wait another 2-3 months and do the same dance again.

Why? Why can Microsoft not learn that an IP has been healthy and spam-free for 10+ years and only bother me when there is actual spam is being sent?

[sheikheddy]

Aww man, not joking this actually breaks my heart, something about the way you wrote it makes it sink in how much we’ve failed you. I’m angry at how much of your time we’ve wasted and this experience is completely unacceptable.

…I think this is just a systemic issue beyond my ability to comprehend, let alone solve, and— I hope I’m wrong about this but honestly when I look ahead it seems the future is only going to get worse for people like you. Which I wish I could phrase in a way that was more kind and respectful, it’s not what anyone wants, these unthinking scars inflicted on email as a medium.

But what I can do is make sure that it’s not worse for you, specifically. If I was perfect I’d attack this rot at its core, but I’m not, so I’ll just solve the problem in front of me even though I know it doesn’t scale and hope God forgives me. Get in touch with me directly and I’ll figure out how to make sure you don’t have to jump through those hurdles again.

[lonelymailer]

Exact same situation as the person you're replying to, except ~5y instead of 10 and I gave up trying getting unblocked after at one point even the mandated reply to an automatic follow-up e-mail a few steps down the line of the appeal-chain got blocked. That behavior was consistent over multiple weeks of retrying. It was truly kafkaesque but I resorted to just not being able to email Outlook/MS recipients. Getting an outreach from someone who wants to get in touch and not being able to reply is the most frustrating. So many people probably believe I ghost them.

Outgoing email volume is a handful a week, zero automation ever, and I must have spent dozens if not in the low hundreds of hours over the years on e-mail deliverability to Microsoft alone until finally giving up. Not comparable to anywhere/anyone else.

Just to say, behind every single false-positive is a story like mine and TonyTrapp. Missing out on a group tour with the local club. An old lost friend or family member not being able to get back in touch. Missed recruitment opportunities. A lawyer not receiving a time-sensitive follow-up.

[TonyTrapp]

Appreciated. How can we get in touch?

[sheikheddy]

Abdurraheem dot ali at microsoft dot com

[TonyTrapp]

Sent you a mail. Hopefully it's not blocked by Microsoft's servers. ;)