Exchange 2003-Outlook 2003 Missing Recipient Field

I have run across a weird problem running Exchange 2003 and Outlook 2003.

A couple of users have occasionally sent emails to a local recipient(s) (in the same domain) where the recipient field (the TO: field) is blank even though the email is delivered successfully.

Looking at the Sent Items folder the email continues to show no recipient.

I have saved a couple of these emails as a .msg file and looked at them with a text editor and compared them to emails that display properly.

I see the following strangeness.

The X.500 address (legacyExchangeDN) is in the email body 3 times with a mixture of capitalization structures for the recipient.

When the email displays properly the recipient format in the msg file looks like this:


On the emails where the recipient does not display, the recipient format is exclusively upper case (still 3 entries)


In ASDIEDIT the specific legacyExchangeDn is:


When I look at the Exchange Tracking log to see what the server logged as the mail passed though the pattern is largely repeated

One of the emails had 7 recipients, only 2 which showed in the Outlook recipient field, which looked as follows:

;;;;;;Zack Wilbur;Jim Smith

The tracking log recorded the following recipient information:


This last sequence was, as expected, repeated each time for the various tracking codes Microsoft uses to process email. (1027, 1019, 1025, and 1024 for X.500 and 1033, 1036, 1023, and 1028 for SMTP)

The emails are being delivered successfully.  The 2 users I know that occasionally have this issue are remote users at the far end of a VPN connection from the server.  I have yet to see an in-facility user with the issue.

Does anyone know why Microsoft writes the X.500 address 3 times in the email but only one time in the tracking log and why should case sensitivity be an issue?
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Fred_AlcibiadesConnect With a Mentor Author Commented:
This turned out to be a conflict between the WAN optimizing software and the firmware on the firewall/VPN endpoint device
Satya PathakLead Technical ConsultantCommented:
I would suggest you can go through.
Fred_AlcibiadesAuthor Commented:
Thanks for the suggestion but it seems unrelated to the issue I have.

There is no duplication problem with the legacyExchangeDN and Exchange 5.5 was never a player in the situation.

I have discovered that the Outlook address cache file reflects that same capitalization weirdness, although it is not clear if that is a cause or symptom.  Either way, clearing the cache did not resolve the issue.
What was the WAN optimizing software?
What was the firewall/VPN endpoint device want what was the firmware version?
What was the conflict?
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