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I have a number of secure emails sent to my Outlook 2007 client. Most arrive fine and display the prompt with regards to granting access to the certificate and then open. Today I received two that crash Outlook whenever I try to open them. I've tried restarting Outlook and my computer but still have the same problem.

Any ideas what might be causing this, and how I can fix it?

I'm working on Windows Vista Ultimate 64-bit.

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I would start with basic Outlook troubleshooting. Most crashes occur because of bad 3rd party code.

  1. Run Outlook without addins. Start, type Outlook /safe and press enter. Now try to open your email. If this works it's likely a faulty addin that's causing your problem. You can disable addins by running Outlook as admin and then going to Tools, Security center, Addins, Manage Com-Addins, Remove all addins that are not from Microsoft.

  2. Disable your antivirus e-mail checking feature and any antispam software you might have. Often these cause irreversible damage to e-mails received so the e-mail might need to be resent.

  3. Boot Windows in safe mode with networking to make sure that no 3rd party software can interfere with Outlook.

  4. Create a new Outlook profile ( many issues are caused by a damaged profile )

This is my personal checklist whenever I troubleshoot Outlook and step 1 and 2 solves most of the issues.

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Make sure the issuer of the certificate is not a rogue CA intended to try to exploit a vulnerability in your MS code that checks to see if the certificate is still valid or if it has been revoked/compromised.

You can usually do this by saving the certificate and looking at the details. Unplugging the network card to keep it from talking to the remote CA for Certificate Revocation List Retrieval might also help in this process. Pull the cable from the wall, open the message and see if it still does it.

Beyond that I would recommend getting a good insightful program that will let you pick the crashing process apart. Sysinternals has some nice utilities which collectively are capable of giving you enough insight to see what is going on. Saving the dump file is also helpful. You should be able to figure out exactly what the error was by looking through the dump file.

TCPDUMP,PROCESS EXPLORER, FILEMON are the essential tools.

Post more info after you know more.

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