We have a strange issue with our Exchange 2003 (Standard Edition) server that's been ongoing for at least a month now. Sometimes when someone at our organization is sent an email with a .DOC attachment, that email is never received. We have a fairly simple setup. A single exchange box. We have the latest Symantec A/V for exchange installed on it. All our incoming and outgoing mail is also filtered by Postini. I can see the incoming emails in the SMTP logs, however the never show up in the user's mailbox, nor are they available via message tracking. Since the messages show up in the SMTP logs, I doubt Postini is at fault. Symantec doesn't show anything in it's logs either. I confirmed that while Symantec was configured to block some attachments, *.DOC was not one of them. I also verified this same behavior exists when I disable the Symantec Content Filtering. The sender receives no NDR or other notification when this occurs, so you can see where this begins to get problematic. CEO doesn't receive important emails with important docs attached, sender assumes they were received as they did not have any notice that they were not, and days later when the CEO hasn't responded, yours truly has a problem. Exchange is running on a Win2003r1 box. Any help would be greatly appreciated. Krev

Turn off or uninstall Symantec, if temporarily, and see if the problem goes away. -- Ed Crowley MVP"There are seldom good technological solutions to behavioral problems.". "Krevlorne" wrote in message news:b9bad06c-74e1-416b-a881-ce6f6165acb9...We have a strange issue with our Exchange 2003 (Standard Edition) server that's been ongoing for at least a month now. Sometimes when someone at our organization is sent an email with a .DOC attachment, that email is never received. We have a fairly simple setup. A single exchange box. We have the latest Symantec A/V for exchange installed on it. All our incoming and outgoing mail is also filtered by Postini. I can see the incoming emails in the SMTP logs, however the never show up in the user's mailbox, nor are they available via message tracking. Since the messages show up in the SMTP logs, I doubt Postini is at fault. Symantec doesn't show anything in it's logs either. I confirmed that while Symantec was configured to block some attachments, *.DOC was not one of them. I also verified this same behavior exists when I disable the Symantec Content Filtering. The sender receives no NDR or other notification when this occurs, so you can see where this begins to get problematic. CEO doesn't receive important emails with important docs attached, sender assumes they were received as they did not have any notice that they were not, and days later when the CEO hasn't responded, yours truly has a problem. Exchange is running on a Win2003r1 box. Any help would be greatly appreciated. Krev Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

Also try sending a .doc attachment as something else as .txt. See if it's just looking at the extension. Mark Morowczynski|MCT| MCSE 2003:Messaging, Security|MCITP:EMA 2K7,EDA Win 7,ES,SA,EA|MCTS:Windows Mobile Admin|Security+|http://almostdailytech.com

Also try sending a .doc attachment as something else as .txt. See if it's just looking at the extension. Mark Morowczynski|MCT| MCSE 2003:Messaging, Security|MCITP:EMA 2K7,EDA Win 7,ES,SA,EA|MCTS:Windows Mobile Admin|Security+|http://almostdailytech.com Mark, I tried this, and the DOC, renamed to TXT also did not come through. Someone outside this forum suggested disabling size limits on in and outgoing mail. That did not help either.

Turn off or uninstall Symantec, if temporarily, and see if the problem goes away. -- Ed Crowley MVP"There are seldom good technological solutions to behavioral problems.". "Krevlorne" wrote in message news:b9bad06c-74e1-416b-a881-ce6f6165acb9... We have a strange issue with our Exchange 2003 (Standard Edition) server that's been ongoing for at least a month now. Sometimes when someone at our organization is sent an email with a .DOC attachment, that email is never received. We have a fairly simple setup. A single exchange box. We have the latest Symantec A/V for exchange installed on it. All our incoming and outgoing mail is also filtered by Postini. I can see the incoming emails in the SMTP logs, however the never show up in the user's mailbox, nor are they available via message tracking. Since the messages show up in the SMTP logs, I doubt Postini is at fault. Symantec doesn't show anything in it's logs either. I confirmed that while Symantec was configured to block some attachments, *.DOC was not one of them. I also verified this same behavior exists when I disable the Symantec Content Filtering. The sender receives no NDR or other notification when this occurs, so you can see where this begins to get problematic. CEO doesn't receive important emails with important docs attached, sender assumes they were received as they did not have any notice that they were not, and days later when the CEO hasn't responded, yours truly has a problem. Exchange is running on a Win2003r1 box. Any help would be greatly appreciated. Krev Ed Crowley MVP "There are seldom good technological solutions to behavioral problems." Ed, Thanks for the response. I have yet to attempt this because, its not something I want to play with in the middle of the day. I may attempt it while I am at the office doing other things this weekend. I will let you know.

Hi,Since the message only shows up in the SMTP log not Message Tracking log, this indicates the email is still processed in SMTP session not passed to the queue of Exchange for processing. And the attachment was also faild to deliver even though it was renamed to .txt.It seems that the third party event sink has casue this issue. As Ed said, you can try turn off or uninstall Symantec to check this issue.ThanksAllen

Tried it this morning with Symantec Info Security for Exchange and Symantec Endpoint Protection completely disabled, and still no good. I suppose it COULD be Postini, but it would surprise me as if Postini were blocking something I wouldn't expect it to reach the SMTP log. but that's where I'm focusing now. Upon further investigation of the Postini logs, it processes the message and passes it down the the exchange server. I cant guarantee it's not modifying the message in some way, but as far as Postini is concerned the mail is good and it's passing it along.