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.
helpdesk_compsychAsked:
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AmitIT ArchitectCommented:
Can you post the header details for delayed message. I can check which server it is delayed.
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helpdesk_compsychAuthor Commented:
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
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AmitIT ArchitectCommented:
Put header info in this url and then check, where it is delayed:
http://mxtoolbox.com/EmailHeaders.aspx
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helpdesk_compsychAuthor Commented:
Yeah that just shows the delay between the two servers but doesn't say who
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AmitIT ArchitectCommented:
I might focus on spam filter server. Any way to bypass it. just to rule it out.
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helpdesk_compsychAuthor Commented:
I did that and the problem persists
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helpdesk_compsychAuthor Commented:
Found the issue.  Microsoft is removing support for TLS 1.0 on their Exchange Online Protection servers and our Spam server is on Server 2003.
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AmitIT ArchitectCommented:
You better move to 2010.
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helpdesk_compsychAuthor Commented:
Microsoft troubleshooting logs identified the TLS errors
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AmitIT ArchitectCommented:
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.
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