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Mail Delivery Delay

Having numerous inbound email delays from 2-4 hours from external senders. Have a ticket open with Microsoft Exchange Online Protection where our inbound mail hits first and then to our Internal Smart Host spam filter which passes it to Exchange 2010.

Our Smart Host spam filter is using (Server 2003) IIS 6 and on the SMTP Virtual Server under Current Sessions I see alot of sessions to Exchange Online Protection with Connected Time anywhere from 0 and 5 seconds to 286 seconds. Is there a log to show why the Connected Time is extremely high or is this normal? I'm assuming all SMTP connections should be a few seconds only when refreshed.

Amit

Can you post the header details for delayed message. I can check which server it is delayed.

helpdesk_compsych

ASKER

The message was sent at 10:24am and received by me at 12:40pm

Received: from server.company.int (x.x.x.x) by
email.company.int (x.x.x.x) with Microsoft SMTP Server id
14.3.224.2; Wed, 24 Jun 2015 12:40:04 -0500
Received: from na01-bn1-obe.outbound.protection.outlook.com ([207.46.163.143])
by email.company.int over TLS secured channel with Microsoft
SMTPSVC(6.0.3790.4675); Wed, 24 Jun 2015 12:40:05 -0500
Received: from CY1PR0201MB1596.namprd02.prod.outlook.com (10.163.140.143) by
CY1PR0201MB1545.namprd02.prod.outlook.com (10.163.139.24) with Microsoft SMTP
Server (TLS) id 15.1.195.15; Wed, 24 Jun 2015 15:24:29 +0000

truncated.....

Received: from BY2PR02CA0107.namprd02.prod.outlook.com (10.163.44.161) by
CY1PR0201MB1596.namprd02.prod.outlook.com (10.163.140.143) with Microsoft
SMTP Server (TLS) id 15.1.195.15; Wed, 24 Jun 2015 15:24:29 +0000
Received: from BY2FFO11FD021.protection.gbl (2a01:111:f400:7c0c::176) by
BY2PR02CA0107.outlook.office365.com (2a01:111:e400:5261::33) with Microsoft
SMTP Server (TLS) id 15.1.195.15 via Frontend Transport; Wed, 24 Jun 2015
15:24:29 +0000

Amit

Put header info in this url and then check, where it is delayed:
http://mxtoolbox.com/EmailHeaders.aspx

helpdesk_compsych

ASKER

Yeah that just shows the delay between the two servers but doesn't say who

Amit

I might focus on spam filter server. Any way to bypass it. just to rule it out.

helpdesk_compsych

ASKER

I did that and the problem persists

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helpdesk_compsych

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Amit

You better move to 2010.

helpdesk_compsych

ASKER

Microsoft troubleshooting logs identified the TLS errors

Amit

If issue is at other end, I don't see anyone can fix it without calling vendor. That's one problem I see with lot of customer when moving to cloud solution. Not sure how MS is allowing 2003 as it is already out of support.