Topic: Mail sent to hotmail addresses fails, no ndr, nothing in the logs

[bosco555]

Hi all,
Bit of a strange one...Mail sent to hotmail addresses does not reach the recipient/s, it just vanishes. No "NDRs", nothing in the logs. Funny thing is that hotmail email can be received OK and if you reply to that email/s, it is received by the hotmail recipient.
I checked and SPF/PTR/ are all good. Antispam blocklists are all clear.
This has got me stumped. And I searched, but as usual M$ has nothing of value.
This is an SME9.2 with all latest updates, user vacations and backup contribs only...

Thanks to all in advance
gb

[ReetP]

Can you show log extracts from both mails? i.e the successful replied one and unsuccesful new ?

Is the mail actually received upstream?

My gut instinct is it's a M$ issue but better to check logically that this is the case

[bosco555]

HI there and thanks for the reply....I looked in those logs with anything to do with Hotmail, but found nothing.
I looked in reasons for failure and success, but nothing shows

OK so just to clear things:
When email is sent from SME to Hotmail, it just vanishes
When email is sent from Hotmail to SME it is received
When replied to above email from SME it is received at the Hotmail address..

I also think it is a M$ issue, as this is only happening with Hotmail addresses and all other free mail providers are fine...

[ReetP]

HI there and thanks for the reply....I looked in those logs with anything to do with Hotmail, but found nothing.
I looked in reasons for failure and success, but nothing shows

First, have you checked the mail queues? Just wondering if it is sat in a queue somewhere on your server. qmHandle etc should help.

OK so just to clear things:
When email is sent from SME to Hotmail, it just vanishes
When email is sent from Hotmail to SME it is received
When replied to above email from SME it is received at the Hotmail address..

I also think it is a M$ issue, as this is only happening with Hotmail addresses and all other free mail providers are fine...

Oh what fun with M$

I think you may need to try something like manually testing the connection by telnetting to the mail server and sending a mail manually and see what happens. There are some examples here somewhere either in the forums or on the wiki I think. Someone with a greater mind than mine should be able to help you debug it a bit more.

This one is a tad ironic but tells you roughly what to do https://technet.microsoft.com/en-us/library/aa995718(v=exchg.65).aspx

I think you need to get your password base64 encoded somewhere:

Code: [Select]

perl -MMIME::Base64 -e 'print encode_base64("user");'

Code: [Select]

perl -MMIME::Base64 -e 'print encode_base64("password");'
Let us know what happens.....

[Daniel B.]

The email can't just vanish, at least, not on your side. It's either still in qmail queue (if outlooks.com's server responds with a deferal, if there's a temp DNS issue etc...), rejected, in which case you should be notified, or sent. If it's sent, it doesn't mean the email is in your recipient's mailbox, just that it's now up to outlook.com to do its job. /var/log/qmail/current will tell you in which situation you are.

[bosco555]

Hi guys..

this is what I get from cat /var/log/qmail/current | grep hotmail

@400000005a28b6f03735c424 starting delivery 10367: msg 57411708 to remote djames@hotmail.com
@400000005a28b7621aa8e1ec info msg 57411708: bytes 10127 from <djames@hotmail.com> qp 29219 uid 453

Now.. there are a lot of these, the above is just one example.

thanks again
gb

[Daniel B.]

Don't use grep to look at qmail logs. For example here, check for the delivery 10367 to see how it ended.

[bosco555]

Hi Daniel...this is what I get:

@400000005a28b6f03735c424 starting delivery 10367: msg 57411708 to remote djames@hotmail.com
@400000005a28b6f40357ef24 delivery 10367: success: 104.47.45.33_accepted_message ./Remote_host_said:_250_2.6.0_<000801d36f0c$61e22e60$25a68b20$@company_mail.net.au>_[InternalId=58914066439800,_Hostname=CO1NAM04HT030.eop-NAM04.prod.protection.outlook.com]_9566_bytes_in_0.255,_36.616_KB/sec_Queued_mail_for_delivery/

But there's nothing in djames's inbox/junkmail folder..

[Daniel B.]

So your email has been correctly delivered. There's not a lot more you can do on your side. It's up to outlook's server to deliver it on the mailbox of the recipient.