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HTTP/1.1 500 Internal Server Error

Created: 24 Jun 2010 | 3 comments

Here is my situation.  There is a particular Word document that users are trying to attach in Outlook Web Access.  When they browse to the file and then click the attach button, OWA displays “HTTP/1.1 500 Internal Server Error”.  I have researched this and the mentioned cause is Mail Security is probably deleting the attachment upon upload, and then OWA can’t find it and returns the error.  I don't know when this problem started, but I upgraded from 6.0 to 6.5 about a month ago. Not sure if this existed beforehand.

-Message attaches and sends fine in Outlook 2007
-Document is a proposal for clients generated by a tool our users have
-Attaches fine when stopping SMSME service
-Opening document and saving as *.DOC (rather than *.DOCX) uploads fine.
-Errors out in either firefox or IE
-Only filter rule enabled is for open.html/open.htm (delete attachment)

I can’t seem to locate any logs/events to see what might be the problem, only log is the IIS service log noting an error with IP, user info, agent string, etc.  Where else should I look for a log of this?

Server 2003 R2 running Exchange 2003 w/SP2 and SMSME


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groberts's picture

Hi Nate,

Take a look at this document:

Title: 'Outlook Web Access (OWA) Returns "500 internal server error" When Attempting to Attach Files Larger Than One (1) Megabyte with Symantec Mail Security for Microsoft Exchange (SMSMSE) Running'
Document ID: 2010021816013354
> Web URL:

This might be your situation, see if the workaround works for you. If it does not, we'll definitely want to do some in depth troubleshooting, this type of process is best done via a support case.

GrimGrinningGhost's picture

I have also started seeing this issue, and discovered the article about the workaround.  While the workaround is good information, I'm wanting a solution.  Has this issue ever been resolved in an update?

utahbmxer's picture

Yeah seriously. I know that ES2003 has reached it's end of life, but maybe this is a Symantec problem.  I've tested the workaround and it works, but the only problem is that there are not many of our employees that use IE.  This needs some more attention.