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User can't open encrypted email in Outlook when she is the CC: recipient

The user is running Outlook 2010. Our server is SBS 2008 with Exchange 2007.
The user has a new cert from Sandra earlier today. The user can open encrypted email from "Sandra" that is addressed to her, but cannot open encrypted email from the same "Sandra" if she is copied on an email to "Nick".
She can open encrypted email from "Nick".
What do I do to enable her to open the email from Sandra that she is copied on?

Here is the mail she can open:
Email 1 from Sandra

Here is email from "Nick"
Email from Nick
Here is email from Sandra she cannot open:
Email from Sandra that won't open
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Robert Kleinschmidt
Asked:
Robert Kleinschmidt
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1 Solution
 
AmitIT ArchitectCommented:
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Robert KleinschmidtAuthor Commented:
amitkulshrestha:
Thanks for the reply.
http://support.microsoft.com/kb/2621062  applies to Exchange2010, but I am running Exchange 2007. But since it seemed harmless, I added the Contact as the article suggests, but it had no effect. SHe still cannot open one of the emails.
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Robert KleinschmidtAuthor Commented:
Can someone recommend a consultant with expert knowledge of this area that I can pay to answer this question?
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David Johnson, CD, MVPOwnerCommented:
The cc doesn't have the encryption key for the cc'd user, therefor instead of using CC one must use multiple TO: addresses this way multiple messages are created with multiple encryption keys.
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Robert KleinschmidtAuthor Commented:
@ve3ofa

Thank you for your reply!

I tested the idea that cc doesn't have the encryption key by sending an encrypted email with the user listed as a cc. She could read it. Of course she had previously gotten signed email from me and we had exchanged encrypted email as well. How is this test different from what fails above?
Encrypted file readable as CC recipient It is also the case that in the problem reported above, she had previously gotten signed and encrypted email from the sender and from the other recipients.

Is it expected procedure to require that when our clients and vendors try to CC us on an encrypted email that we must reply to them out of band and require them to resend the email with all recipients on the "To:' list and without anyone on the CC line?

Further testing suggests that there seems to be a difference between different "versions" of the email addresses in use. If I type in the user's name on the cc line I may get a match from the Outlook address book which, although the same SMTP address, seems not have a certificate associated with it. How do I remove such ambigous contacts?
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Robert KleinschmidtAuthor Commented:
More thoughts: If she was not in the original email chain, but was later added, she won’t be able to open it. Only the original To:, CC:, or BCC: recipients can open the email.

That was not the case here, but it is a good factoid for others reading this.

I found the following and I will get around to trying the re-import of keys next weekend. ¿
http://support.microsoft.com/kb/258527
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Robert KleinschmidtAuthor Commented:
As described in http://support.microsoft.com/kb/258527 , when I deleted and recreated the Outlook contact for the persons involved in the email thread all the problems went away.

I created the new contacts from the most recently signed email from the contact by right clicking on the sender's name and selecting "Add to Outlook contacts".
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Robert KleinschmidtAuthor Commented:
It worked and I have a pointer to the reference.
I do not have any explanation for the "why" or how to avoid, which I would expect in a "good" or "Excellent" answer.
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