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Outlook 2010 will not send or receive Signed/Encrypted Emails

Posted on 2013-05-16
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Last Modified: 2013-07-31
Hello All:

Detail:  Windows 7 64 Bit, Outlook 2010 64 Bit, Exchange 2010, Testing with users/email accounts in GAL before email goes out to gov't.  Certificate were given by SafeNet to obtain access to Gov't Websites (JPAS and STEPP).
ActiveSync with logon to workstations for exchange.  

Problem:  An Error Occurred in the underlying security system. The Keyset is not defined.

Steps Taken:
Created new profiles
Turned off & on Cache mode
Outlook.exe /safe
Email > Options > Trust Center > Email Security > Default Settings : My S/MIME Settings (kbolt@gbhawk.com)]
Email Security > Settings > Signing Certificate:  Cert given by SafeNet
Email Security > Settings > Encyrption Certificate:  Cert given by SafeNet
Tried sending with & without Send these certificates with messages
Exported & Imported certificate to .CER with my own profile on personal contact

Any Help Would be Greatly Appreciated because I'm going to pull my hair out.

Edit:
http://www.experts-exchange.com/R_21010.html
Modulus_Twelve
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Question by:synertia
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12 Comments
 
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Accepted Solution

by:
Haresh Nikumbh earned 2000 total points
ID: 39171621
The above error message occurs if there is not a digital certificate available for the sender or recipient on your workstation.

Outlook cannnot send a signed or encrypted or in some instances view an S/MIME message.
As a workaround, you can use the following instructions to manage certificates for Outlook 2007 and 2010.

    Open a digitally signed message from the recipient.
    Right-click on the name in the "From:" box and choose "Add to Outlook Contacts"
    The contacts window will open next click on the "Save & Close" button in the upper-left corner.
    Verify this setting in Outlook:UW Digital ID (Win) - Outlook 2007 & 2010 - Messages Display as Encrypted when they are only Signed


http://kb.wisc.edu/page.php?id=23507
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Author Comment

by:synertia
ID: 39171637
takecoffee:  thanks for the fast reply.

Problem.  Internal users are part of the GAL so we can not 'open a digitally signed message from the recipient' when we can't send our cert.
(If I am reading your suggestion correctly)
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Author Comment

by:synertia
ID: 39180789
Update:

Outlook 64 Bit is still not excepting certificate through IdenTrust.  

Following steps also tried:

exported cert & imported cert
tried to publish to GAL in Exchange 2010 --- Permissions stopped in Outlook 2010 and inside Exchange, Error while trying to upload cert
AD on exchange 2010 server > Published Certs > Will not allow me to upload any certs
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Author Comment

by:synertia
ID: 39181134
Update:

OWA not sending certificate as well. Error code: 0x80090020

Contacting IdenTrust.
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Author Comment

by:synertia
ID: 39181753
1 hour with IdenTrust ... Not a cert issue.  GPO or Exchange stopping signing ?
0
 

Author Comment

by:synertia
ID: 39183844
Okay ... Interesting update to anyone following.

I was able to do follow these instructions from MS  http://support.microsoft.com/kb/2497165 and was able to send now on OWA but Outlook 2010 64-Bit is still stopping me.
0
 

Author Comment

by:synertia
ID: 39215936
still having errors. OWA working but really doesn't help ... Need Outlook

Thanks for looking
0
 

Author Comment

by:synertia
ID: 39258716
thanks all experts for the feedback.
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Author Closing Comment

by:synertia
ID: 39269122
Please close ticket as no one responded.  I had to go ahead and spend the money with Microsoft & found it to be an 64-bit problem.  I can not install the 32-bit due to other MS 64 bit products on the workstations.
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