Problem: Automatic Encryption Unchecks itself. Every time the user locks computer and removes PIV card from keyboard, the "Encrypt contents and attachments for outgoing messages" box becomes unchecked, as does the "Add digital signature to
outgoing messages" box, when the user logs back in.
Multiple changes to the registry did not work. Microsoft suggested to check that the key value for: HKCU\Software\Microsoft\Office\14.0\Outlook\Security\InitEncrypt was set the value of 2. It was already.
A full rebuild of the users profile was attempted including renaming and then deleting the old profile both locally and server-side and resulted in the same issue.
The only thing that has worked is this:
1. In Outlook 2010 Click File > Options > Trust Center > Trust Center Settings > E-mail Security > Settings.
2. Click "New" to create a new "Security Settings Name"
3. Enter a new name.
4: Check the boxes for "Default Security Setting for this cryptographic message format" & "Default Security Setting for all cryptographic messages"
5: Select a "Signing Certificate" by clicking on the "Choose" button
6: Select an "Encryption Certificate" by clicking on the "Choose" button.
7: Click "OK"
8: Make sure the new Security Settings Name is selected and that the Encrypt and sign boxes are checked.
When the user unlocks the computer the outgoing emails will still be automatically encrypted.
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Proposed as answer by
tseantownsend AKA BMOREiTGUY
16 hours 35 minutes ago