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MS Outlook had problems encrypting this message...

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Problem: working with two users in a test environment, I see that both can send each other signed email. However:

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- Alan Reid can send Alex Heyne encrypted emails

but

- the opposite is not true (Alex Heyne cannot send Alan Reid encrypted emails).

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Environment: domain, Windows 2003 FFL

- 1 Windows 2008 R2 SP1 domain controller with ADDS and ADCS.

- 1 Exchange 2010 SP3 mail server

- Single CA (it's running on the domain controller)

- Client machine is Windows 7 SP1 with Outlook 2010 SP1

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Preliminary notes:

- Duplicated the "Exchange User" template.

- General Tab of template: Yes, "Publish certificate in Active Directory"is checked.

- Request Handling tab: Purpose: Signature and encryption.

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Other configured settings should be correct since...

- Users automatically obtain the certificate via Group Policy and autoenrollment.

- The certificate does appear in their user certificate store.

- It can be used to sign email messages. The resulting message has the "seal" or "medal" or "ribbon" icon that indicates that it is signed.

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Besides verifying what preceeds:

- In ADSIEdit, the "userCertificate" attribute of both the sender and recipient is populated with a sequence of two digit numbers and back slashes.

This is the result of the certutil command I ran after reading this post:

http://social.technet.microsoft.com/Forums/windowsserver/en-US/531d8e81-f2c8-4b48-9b6f-0318ea204ed1/office-outlook-had-problems-encrypting-this-message-because-the-following-recipients-had-missing-or

C:\>certutil -verify -urlfetch certificatefile.crt
DecodeFile returned The system cannot find the file specified. 0x80070002 (WIN32
: 2)
LoadCert(Cert) returned The system cannot find the file specified. 0x80070002 (W
IN32: 2)
CertUtil: -verify command FAILED: 0x80070002 (WIN32: 2)
CertUtil: The system cannot find the file specified.

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That's the result for either user, even when I run as admin.

I'm going to try with other users right now.

Otherwise, how can I troubleshoot this beyond what I have already done?


Please mark as helpful if you find my contribution useful or as an answer if it does answer your question. That will encourage me - and others - to take time out to help you.


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