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Anyone else here using their own SMTP server on a regular basis?

@oliof I'm partly trying to build up a network of fellow email-admins for problem-solving, but the immediate issue that made me start doing this is:

Have you had any occasion to send email to msn.com, or any other Microsoft-owned domain, lately?

It's now claiming that my IP is blacklisted (and refusing to deliver my messages) & won't say why. Prelim investigation suggests that nobody else is blacklisting it.

I spose I should check other blacklists... but... moreinfoplzMS?? :-P

@woozle that's the reason I use my own mail server mainly for receiving mails from non-person-entities, but send using gmail /-:

Dealing with random blacklisting is frustrating, especially since mail providers sometimes blacklist you if you come from a consumer IP range and/or have something in your config they deem "wrong".

And often the large providers do not give you info on what's wrong because they do not want to tell spammers how to build a legitimately looking service.

@oliof ..said behavior being virtually indistinguishable from "trying to force people to use major services for email" :-P

I guess this is now an open request: has *anyone* been able to successfully deliver email to a Microsoft property from a small server recently?

@schestowitz Has anything about this appeared on your radar?

Harald Wagener @oliof

@woozle @schestowitz do you have an msn address at hand I could try? feel free to PM.

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@oliof @schestowitz I'm going to set up an account for testing purposes (and as a last-ditch effort to get through to a particular individual -- since regular GMail no longer supports delivery confirmation requests). One moment...

@oliof (Oops, I should have removed Schestowitz from that part of the discussion.)

@oliof Okay, here we go: woozalia@outlook.com

I've verified that it can send email to my server and that email from my server is silently eaten unless I request delivery status notification.

@woozle yes, blocked

"Unfortunately, messages from xxx.xxx.xxx.xxx weren't sent. Please contact your Internet service provider since part of their network is on our block list. You can also refer your provider to mail.live.com/mail/troubleshoo. (in reply to MAIL FROM command))"

@woozle the docs at mail.live.com ... say "Mail rejected by Outlook.com for policy reasons. Reasons for rejection may be related to content with spam-like characteristics or IP/domain reputation. If you are not an email/network admin please contact your Email/Internet Service Provider for help."

@oliof

"Rejected for policy reasons" == "rejected for reasons" == "need-to-know, old chap". :-/

The delivery failure report I get back is a bit more specific -- in part: "Please contact your Internet service provider since part of their network is on our block list."

Doesn't say why or how many IP addresses... though I suppose I could file a problem report with DigitalOcean and see if other users have been reporting the same issue.

@woozle I guess they block the address rangrs of all hosting providers (i'm at scaleway), and only people that go through enough paperwork get an exemption ...

@oliof That's more or less my ugly suspicion about what's going on here.

I have 3 other IP addresses I could try emailing from... not all at the same datacenter, either...

If I wanted to get hardcore about this, I could set up a temporary droplet at each of DO's datacenters just long enough to see if it's being blocked.

If they all are, that would be pretty damning, I'd think.