Outlook 2007 Cannot send encrypted emails to certain recipients
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!!!
August 18th, 2010 12:05pm

Hi, Have you read these articles ? How to Digitally Sign and Encrypt Messages in Outlook Express http://support.microsoft.com/?kbid=168726 OE: How to Remove, Import, and Export Digital Certificates http://support.microsoft.com/?kbid=179380 OE: Sent Message May Not Be Digitally Signed http://support.microsoft.com/?kbid=185621 Unable to Use Personal Certificates in Outlook Express http://support.microsoft.com/?kbid=190296 I hope this will help you. Regards. Shafaquat Ali.M.C.I.T.P Exchange 2007/2010, M.C.I.T.P Windows Server 2008, M.C.T.S OCS Server 2007 R2, URL: http://blog.WhatDoUC.net Phone: +923008210320
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August 18th, 2010 2:24pm

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.
August 18th, 2010 5:10pm

Hi I tried the above steps but nothing come in Trusted people. I am able to send encrypted emails to many users but to few i am not able to send. I have reinstalled the certificates but it is the same story again. Regards, Tej Singh
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February 16th, 2011 9:49am

Same issue here. Any solutions?MCTS - Please remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread. http://mariusene.wordpress.com/
May 10th, 2012 5:11am

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