Outlook 2007 Cannot send encrypted emails to certain recipients

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IsaiahNetAdmin

I have a user that is able to send encrypted emails to almost all of his recipients. However, he will get a message that he is unable to send his email encrypted to two specific users. He used to be able to send to them. This just started a couple weeks ago.

Error:

Microsoft Office Outlook had problems encrypting this message because following recipients had missing or invalid certificates, or conflicting or unsupported encryption capabilities. Continue will encrypt and send the message but the listed recipients may not be able to read it.

Below are his Outlook encryption settings...

Unchecked: Encrypt contents and attachments for outgoing messages

Checked: Add digital signature to outgoing messages

Checked: Send clear text signed message when sending signed messages

Unchecked: Request S/MIME receipt for all S/MIME signed messages

Default Setting: My S/MIME Settings (<sendersemailaddress>)

SETTINGS:

Security Settings Name: My S/MIME Settings (<sendersemailaddress>)

Cryptography Format: S/MIME

Checked: Default Security Setting for this cryptographic message format

Checked: Default Security Setting for all cryptographic messages

Signing Certificate: <User's Name> Verisign, Inc. ID

Hash Algorithm: SHA1

Encryption Certificate: <User's Name> Verisign, Inc. ID

Encryption Algorithm: AES (256-bit)

Checked: Send these certificates w/ signed messages

CERTIFICATE DETAILS:

VeriSign Class 1 Individual Subscriber CA - G2

Valid from 11/12/2009 to 11/13/2010

****************************************

I have tested unchecking the " Add digital signature to outgoing messages" and " Send clear text signed message when sending signed messages" options and the same error comes up.

Does anyone have any ideas what may cause this or how to fix it??

Many Thanks!!!
 
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IsaiahNetAdmin

Yes, I've read these articles. I understand the process for creating and importing digital certificates and how to set Outlook to encrypt emails. These articles don't really apply or help w/ my issue.
 
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