Outlook.com is deleting mail at random

Tags: websites, e-mail.
By lucb1e on 2013-09-13 15:02:35 +0100

Just a heads up warning for everyone: over the past week I've noticed that Outlook.com is randomly but consistently not delivering certain e-mail. It may or may not affect you, I'm not sure what triggers the error.

As you may have read before I am using a somewhat odd way of handling email and email addresses. So far it has always worked fine and the only spam I get is legacy stuff that is not using my new system. So I can really recommend this, plus it sparks interesting conversations at times.

So what happens is this:

1. I sign up for example.com with the email address example.com@lucb1e.com

2. Example.com wants to verify I really own that address and send me a confirmation link or code.

3. Lucb1e.com has its own mailserver (yay for my ISP, XS4ALL, allowing port 25!). The mail that example.com sends arrives at my server.

4. My mailserver receives the email and forwards it to my inbox at outlook.com.

5. Email shows up in my inbox.

This worked all neat and great until last week when someone should have mailed me, but hadn't. I reminded him, he sent another e-mail, and again it didn't arrive.

Puzzled, of course, I dug into the logs. Here is what the logs show:

"SMTPD"	2988	79	"2013-09-05 16:50:45.196"	"<remote IP>"	"SENT: 220 Welcome to lucb1e.com mailserver. Contact: [removed]"

"SMTPD"	3024	79	"2013-09-05 16:50:45.243"	"<remote IP>"	"RECEIVED: EHLO example.com"

"SMTPD"	3024	79	"2013-09-05 16:50:45.243"	"<remote IP>"	"SENT: 250-lucb1e.com[nl]250-SIZE[nl]250 AUTH LOGIN"

"SMTPD"	2844	79	"2013-09-05 16:50:45.290"	"<remote IP>"	"RECEIVED: MAIL FROM:<user@example.com> SIZE=2068"

"SMTPD"	2844	79	"2013-09-05 16:50:45.305"	"<remote IP>"	"SENT: 250 OK"

"SMTPD"	3604	79	"2013-09-05 16:50:45.336"	"<remote IP>"	"RECEIVED: RCPT TO:<example.com@lucb1e.com>"

"SMTPD"	3604	79	"2013-09-05 16:50:45.492"	"<remote IP>"	"SENT: 250 OK"

"SMTPD"	3456	79	"2013-09-05 16:50:45.539"	"<remote IP>"	"RECEIVED: DATA"

"SMTPD"	3456	79	"2013-09-05 16:50:45.539"	"<remote IP>"	"SENT: 354 OK, send."

"SMTPD"	4084	79	"2013-09-05 16:50:45.648"	"<remote IP>"	"SENT: 250 Queued (0.093 seconds)"

"APPLICATION"	484	"2013-09-05 16:50:45.648"	"SMTPDeliverer - Message 19978: Delivering message from user@example.com to [internal forwarding account]. File: path/file.eml"

"SMTPD"	3500	79	"2013-09-05 16:50:45.851"	"<remote IP>"	"RECEIVED: QUIT"

"SMTPD"	3500	79	"2013-09-05 16:50:45.851"	"<remote IP>"	"SENT: 221 goodbye"

"APPLICATION"	484	"2013-09-05 16:50:45.867"	"SMTPDeliverer - Message 19978: Message delivery thread completed."

"APPLICATION"	484	"2013-09-05 16:51:45.849"	"SMTPDeliverer - Message 19979: Delivering message from example.com to user@hotmail.com. File: path/file.eml"

"TCPIP"	484	"2013-09-05 16:51:45.849"	"DNS - MX Lookup: hotmail.com"

"TCPIP"	484	"2013-09-05 16:51:46.192"	"DNS - MX Result: 48 IP addresses were found."

"TCPIP"	484	"2013-09-05 16:51:46.192"	"Connecting to 65.55.92.136..."

"SMTPC"	3604	80	"2013-09-05 16:51:46.785"	"65.55.92.136"	"RECEIVED: 220 SNT0-MC1-F10.Snt0.hotmail.com Sending unsolicited commercial or bulk e-mail to Microsoft's computer network is prohibited. Other restrictions are found at http://privacy.microsoft.com/en-us/anti-spam.mspx. Thu, 5 Sep 2013 07:51:43 -0700 "

"SMTPC"	3604	80	"2013-09-05 16:51:46.785"	"65.55.92.136"	"SENT: HELO lucb1e.com"

"SMTPC"	3004	80	"2013-09-05 16:51:46.941"	"65.55.92.136"	"RECEIVED: 250 SNT0-MC1-F10.Snt0.hotmail.com (3.19.0.77) Hello [83.161.210.237]"

"SMTPC"	3004	80	"2013-09-05 16:51:46.941"	"65.55.92.136"	"SENT: MAIL FROM:<example.com>"

"SMTPC"	3604	80	"2013-09-05 16:51:47.097"	"65.55.92.136"	"RECEIVED: 250 example.com....Sender OK"

"SMTPC"	3604	80	"2013-09-05 16:51:47.097"	"65.55.92.136"	"SENT: RCPT TO:<user@hotmail.com>"

"SMTPC"	2988	80	"2013-09-05 16:51:47.315"	"65.55.92.136"	"RECEIVED: 250 user@hotmail.com "

"SMTPC"	2988	80	"2013-09-05 16:51:47.315"	"65.55.92.136"	"SENT: DATA"

"SMTPC"	3836	80	"2013-09-05 16:51:47.487"	"65.55.92.136"	"RECEIVED: 354 Start mail input; end with <CRLF>.<CRLF>"

"SMTPC"	3836	80	"2013-09-05 16:51:47.487"	"65.55.92.136"	"SENT: [nl]."

"SMTPC"	3940	80	"2013-09-05 16:51:48.516"	"65.55.92.136"	"RECEIVED: 250  <someuniquecode.squirrel@example.com> Queued mail for delivery"

"SMTPC"	3940	80	"2013-09-05 16:51:48.516"	"65.55.92.136"	"SENT: QUIT"

"SMTPC"	3448	80	"2013-09-05 16:51:48.657"	"65.55.92.136"	"RECEIVED: 221 SNT0-MC1-F10.Snt0.hotmail.com Service closing transmission channel"

"APPLICATION"	484	"2013-09-05 16:51:49.109"	"SMTPDeliverer - Message 19979: Message delivery thread completed."

Private info has been removed: sender has been replaced with user@example.com, sender IP has been replaced with <remote IP>, recipient with example.com@lucb1e.com, and my hotmail/outlook.com inbox with user@hotmail.com. The log is otherwise untouched.

Note the emphasized part at 16:51:48.516 where Hotmail/Outlook.com told my server it was queued for delivery to my account. Unlike with other e-mail though, it never arrived.

And yes, I do know how to check my spam folder. It's not in deleted mail or any other folder either. I also think it's unlikely someone permanently erased it for me; I was watching the delivery queue on my mailserver's admin panel and as soon as the mail was delivered I checked my inbox. It usually arrives instantly.

A few days ago this happened again. I caught the email in the temporary folder of my mailserver and was able to verify my account, but for some odd reason I let it go and didn't call it quits on outlook.com yet.

Today this happened again when signing up for honeydocs.com; it's all in the logs but on outlook.com it's a total no-show. And I did send multiple confirmation emails to be sure.

Testing when I send email from outlook.com to myself (which goes through the mailserver at home) or test from another small, private mail service, everything arrives right on schedule.

Conclusion
All I know right now is that Outlook.com is selectively withholding emails from me, either based on contents, headers, or original origin address, I don't know. At any rate, a temporary account that I setup at my mailserver works fine with Thunderbird. Thunderbird is really awesome by the way, much better than the Windows Live Mail I had to setup for some others lately. And of course it's 100x more NSA-proof after configuring my SSL certificates (it'll warn me if it ever changes), so I guess I'll go with using that from now on for all e-mail.

Outlook.com did not respond to my request for comments.