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Yardstick

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Exchange 2013, emails with attachments are not sending, but not throwing NDR's

When our client sends a PDF, they get a delay notification.  When sending a non-attachment email it goes through fine.  When any PDF is attached, the Queue Viewer is stuck in retry

Identity: servername\619\87716117086273
Subject: RE: Ticket#561854/somecompany/EMAIL - BOUNCEBACK - Delivery delayed -- has been updated
Internet Message ID: <be62c95131f346e69eeecc4125b42299@servername.somecompany.local>
From Address: june@somecompany.com
Status: Retry
Size (KB): 33
Message Source Name: SMTP:Default servername
Source IP: 10.122.216.16
SCL: -1
Date Received: 2/22/2017 11:59:43 AM
Expiration Time: 2/24/2017 11:59:43 AM
Last Error: 451 timeout (#4.4.2)
Queue ID: JW-EXCH1\619
Recipients:  support@nosoup4u.com;3;2;[{LRT=};{LED=451 timeout (#4.4.2)};{FQDN=};{IP=}];0;CN=NEwReflexion,CN=Connections,CN=Exchange Routing Group (DWBGZMFD01QNBJR),CN=Routing Groups,CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=First Organization,CN=Microsoft Exchange,CN=Services,CN=Configuration,DC=somecompany,DC=local;0

I have recreated the send connector and restarted the server
I have tried changing the mail type, but this is not the solution they want

Any thoughts?
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Obi Wan
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Maybe the recipients are using  greylisting and/or tarpitting which may cause your connection to timeout / force retrys

Use telnet or www.wormly.com/test_smtp_server to see if there is a delay experienced when sending mail to or via external relays / edge / permiter devices
And check your Antivirus application, try to sent again after disable AV.
What is the next hop? ISP or Internet? If Exchange is retrying, that means issue with next hop. You might need to focus on next hop or bypass it and check if that works.
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Yardstick

ASKER

Hey thanks for the answers.  I doubt its a greylist issue as all recipients are affected, and only by certain attachments.

I have disabled email protection as well as scanning on the server from ESET

It doesnt even get out of the exchange server, does not hit Reflexion at any point.

Again, this is ONLY happening with emails with PDF attachments
ASKER CERTIFIED SOLUTION
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Saber

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thanks