S/MIME - User receving "Problems Encrypting" Error

I have a user that is having issues sending a file that needs to be encrypted to anyone outside the company.  The encryption tool being used is S/MIME.

When she attempts to send the file via outlook to someone outside the company, she receives the following error message:

"Microsoft Office Outlook had problems encrypting this message because the following recipients had missing or invalid certificates, or conflicting or unsupported encryption capabilities"

The weird thing is that she is the only one having this issue as two others using the same tool are having no issues what so ever.  IT should be known that all systems are win7 /w office 2007.  

One of the guys in our security group who installed the program thinks outlook should be reinstalled, but says he really isn't sure what the issue is.

Any help on this would be appreciated.


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Are you sure she has the recipient's certificate? If she doesn't she will have to add it to the contact info.  To do that she must receive a digitally signed email from the intended recipient, then she will have to right clck the name in the From box, and then click Add to Contacts on the shortcut menu.  Only then will she be able to send that person an encrypted email.

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Mangi05Author Commented:

You might make a great point.  It should be known that this user just had her machine migrated from XP to Win7.  Since that time she has not be able to send these documents to any recipients.  This is the only application IT does not manage as this is something security handles completely.  The security guy is not sure what the problem is, but this makes sense.  With a new image, all the previous certs are gone.  I will work with the user tomorrow and respond back with an outcome.  Thank you for your help.  Stay tuned.  
Mangi05Author Commented:
Spoke with the user today.  She said that she has tried to add the contact information and has received a digitally signed email from the intended recipient.  She has added the certificate and all would seem fine until she goes to send something to the user.  She would then check the cert for the particular user and it would no longer exist.

Did you verify that she did the import correctly?  Maybe she started the import then when she was asked if she wanted to replace the existing contact with this new information she said no fearing she would lose her contact.  I would have her do it again and watch.
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