Outlook crash when using Attach to Email...

Question

Strange problem occurring when attempting to email a pdf.
I have the document open in Acrobat. I hit the Attach to Email button and a new Outlook email window opens and attaches the pdf. No problem there.
I fill in the addressee name and then begin to write my preamble. If I send RIGHT AWAY, the email goes without a problem.
If I take more than 30 to 45 seconds, a timeout of some kind occurs and Outlook crashes the second I hit the Send button.
This issue has happened to myself and several users in-house on various occasions, never predictable and random. It has gotten to the point that we are afraid to leave the email and just power it out quickly, hoping that Outlook won't crash.
We are all using Outlook 2003 and Acrobat 8 Standard, fully updated and current.
Some help would be appreciated.
Thanks!

Answer 1

I have been seeing this off and on. It is rarely consistent and I have been waiting to find a PC that could reproduce this. I finally got one and was able to reproduce the issue about a dozen times back to back, often when the message has been open for a couple minutes. I have been using Windows Debug tools to isolate the culprit and capture a dmp file to analyze. In each instance of the problem a hang is produced after clicking OK to the message. This is where I have been starting the capture. In our case all the dumps of outlook.exe show the culprit as being valkyrie.dll, an add-in associated with Symantec Enterprise Vault. After disabling the add-in, the issue could not be reproduced. I am not 100% convinced though. I would like to know if other dumps outside of our environment point to the same culprit.
To capture a dmp file you will need to install the debugging tools for windows from Microsoft. Once installed, go into the folder where it is installed (C:\Program Files\Debugging Tools for Windows (x86) by default) and run adplus.vbs. Dont worry about the details now, just click OK or Yes to the prompts. You will use adplus from the command line when the issue happens. To do this:
Create the problem and click OK to the "The operation failed due to network or other communication problems. Check your connections and try again". Outlook should become unresponsive/hung up.
Open command window (Start>Run and type cmd).
Navigate to the folder where the debugging tools were installed (cd c:\program files\debugginf tools for windows (x86))
Create a dmp file by running the following: adplus -hang -pn outlook.exe (-hang will tell adplus that a there is a hung application you wish to dump and -pn specifies the process name).*
A dialog box will indicate that a folder has been created in the windows debugging folder. It will be named something like Hang_Mode__Date_... The date and time will correspond to the date and time of when the dump took place. Go into this folder and verify there is a .dmp file. The name of the file corresponds to the process ID of the process, the process name, and date and time. The file can be fairly large since it consists of a memory dump.
To analyze this file, open Windbg from the exe or from Start>Programs>Debugging Tools for Windows>WinDbg.
Go to File>Open Crash Dump and locate the file above.
Dont worry about all the jiberish you initially see. In the empty line at the bottom run the following command: !analyze -v. While the file is being analyzed, the status message will say BUSY. Dont worry about the "Error: Symbol file could not be found..."
Look for the FAULTING_MODULE and MODULE_NAME. In our case the culprit this was ntdll and Valkyrie. As mentioned above, Valkyrie.dll is associated with the Symantec Enterprise add-in and this is what we are currently looking at with Symantec.
This is an example of the dump:
*If outlook is crashing instead of getting hung up, then you will need to run adplus in crash mode instead. This needs to be done before the problem is created as opposed to waiting when outlook become hung. To do this run adplus -crash -pn outlook.exe. The dmp file will be created once Outlook has crashed in the windows debugging folder.