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Hotmail/Outlook.com incoming mail servers are lying b******

Well, the title almost says it all. I’m using postfix, in a setup which I previously explained, to forward e-mails sent to myemail@mydomainnames.com to both a Hotmail and a Yahoo mailbox. I made this choice for the sake of redundancy, after getting tired of suffering from their rare yet still too frequent downtimes, but also historically because I wasn’t sure which one to use primarily. In the end, after big issues with Yahoo (mainly, block from sending e-mails by their broken anti-spam bot), I picked Hotmail.

Recently, I was expecting an e-mail, and it never arrived. Luckily, we had other ways of communicating, so I went to my now secondary e-mail box (Yahoo) and looked for it. And there it was. So what happened to the e-mail on the Hotmail/Outlook side?

1) It didn’t land in spam: I regularly check the spam folder, and although I give only a quick glimpse at most of the stuff in it, I don’t think I’d miss something in French, from someone with a French name. The spam I get is usually in English, or, less commonly, some funky language such as Russian or Chinese.

2) But it wasn’t rejected either. It was f***ing silently discarded. I eventually dug up the e-mail from my postfix log. Here’s the line:
Dec 6 10:32:46 81-7-10-146 postfix/smtp[6598]: D865A1166611: to=<[me]@hotmail.com>, orig_to=<[me]@mydomain.com>, relay=mx2.hotmail.com[65.55.92.136]:25, delay=2.8, delays=1.6/0.01/0.43/0.77, dsn=2.0.0, status=sent (250 <52A199B9.8020101@gmail.com> Queued mail for delivery)
That’s not a rejection, that’s a clear accept. Another e-mail passed just a few minutes later and it looked like this:
Dec 6 10:39:05 81-7-10-146 postfix/smtp[7457]: 65D2B1166004: to=<[me]@hotmail.com>, orig_to=<[me]@mydomain.com>, relay=mx3.hotmail.com[65.55.92.136]:25, delay=2.3, delays=1.2/0/0.44/0.6, dsn=2.0.0, status=sent (250 <52A18C48.307060@example.com> Queued mail for delivery)

So, Hotmail is silently discarding some of your e-mails, for no good reason, and not telling you about it. I dug up a bit and also found an e-mail from a merchant I recently ordered from. Not a newsletter, but a question related to the order. So definitely some other e-mail which didn’t look like spam AT ALL. What the flip does Micro$oft think they’re doing with their lame filters?

Update: just found this post of someone having the same problem, looks like I’m not the only one having trouble with them.

Posted in Microsoft, web filtering.


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