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E-mail Not Going Out

Created: 17 Mar 2011 | 7 comments

Hi I have PGP 10 installed on my computer and I've been sending e-mails for about 2 weeks now with no problem but 2 days ago I sent an e-mail via Outlook and the e-mail moved to my Sent Items folder but my Exchange server never picked it up (looking at Exchange Tracking Logs). I went to the PGP logs and it shows the following:

"This one is an e-mail that was sent successfully"

15:47:42 Email Info    Processing outgoing message from SENDER <SENDER@MYCOMPANY.COM> with subject: SUBJECT_1
15:48:06 Email Info    Sending unsecured message to RECIPIENT_1, RECIPIENT_2, RECIPIENT_3, RECIPIENT_4
15:48:06 Email Info   Encrypting PGP Partitioned message to RECIPIENT_WITH_PGP with key(s):
15:48:06 Email Info      'RECIPIENT_WITH_PGP <RECIPIENT_WITH_PGP@MYCOMPANY.COM>' (XxXXXXXXXX:XxXXXXXXXX)
15:48:06 Email Info      'SENDER <SENDER@MYCOMPANY.COM>' (XxXXXXXXXX:XxXXXXXXXX)
15:48:06 Email Info   Signing PGP Partitioned message with key 'SENDER <SENDER@MYCOMPANY.COM>' (XxXXXXXXXX)
 
 
"This is the e-mail that never hit my Exchange server"
 
15:55:25 Email Info    Processing outgoing message from SENDER <SENDER@MYCOMPANY.COM> with subject: SUBJECT_2
15:55:27 Email Info    Processing outgoing message from SENDER <SENDER@MYCOMPANY.COM> with subject: SUBJECT_2
 
Additional Information: 
   OS:                Windows XP Professional
   E-mail Client:   Microsoft Outlook 2003
   E-mail Server:  Microsoft Exchange 2010
 
If anyone has any thoughs on this I would be grateful if you'd share.
 
Thanks,
 
David

Comments 7 CommentsJump to latest comment

Tom Mc's picture

While I see in the Release Notes that the current version of PGP (10.1.1) is compatible with Exchange Server 2007, I do not see anything to indicate that it is compatible with Exchange Server 2010 (and it does not support Office 2010), so this may be the problem.

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Demostenes's picture

Have you tried Telnet to check if it is a port issue?

Has the message been queued in the Mail Queue of the Universal Server?

It's true that PGP does not support yet Office 2010, but if it was working for you before, and now it stopped working, there is something in the middle, probably an installation, a modification, some settings configurations. Do you recall any changes being made from when you were able to send emails to when you weren't?

"See, the problem with speculation is you make a speck out of you and some guy named lation"

david_sh's picture

It is just this one e-mail that had problems. Everything else is fine. This is Microsoft Office 2007 and Exchange Server 2010.

The exchange server never saw it come in. Saw all e-mails except this particular one.

Demostenes's picture

Question,

If it is just this mail it might be being filtered, or taken as spam/not wanted email. Is that possible?

Have you ever been able to receive an email from this same account before?

Also, do you have any mail policy set that could be affecting the sending of that particular email?

"See, the problem with speculation is you make a speck out of you and some guy named lation"

david_sh's picture

We don't have any policies in place that effect mail flow.

I sent the e-mail to the exact same people a few minutes before and that one went fine. 

Also this is a problem with an e-mail i sent. Not a problem with receiving e-mails.

Thanks,

LarsG's picture

At one point when I had reached my mailbox (exchange) limit, my messages were not being sent out, nor were they in 'sent items'.

Check to see if you have any exchange policies.

Demostenes's picture

So this happened once. It was an isolated issue right? Because if so, this would narrow the problem. Or does it keep happening to you?

"See, the problem with speculation is you make a speck out of you and some guy named lation"