I'm working on migrating my users from Exchange 2010 to Exchange 2013. Right now I only have my Admin mailbox that I used during the install and then my actual user mailbox on EX13. I followed the below URL which worked.
https://technet.microsoft.com/en-IN/library/dn626158%28v=exchg.150%29.aspx?f=255&MSPPError=-2147217396
Problem I'm having is that when I open an encrypted email it asks to install S/MIME. I download the file but I always get an error messages saying the file is invalid or corrupt. I'm allowed to install it anyway and I do successfully. Now within OWA under Options I have S/MIME settings saying I have the most recent version 4.0500.15.0.1178.4 of S/MIME control installed.
When I create a new email and try to send it encrypted I can't. If I go into S/MIME settings and select "Encrypt contents and attachments of all messages I send" and hit OK, the emails are not encrypted. If I open a new email and go to "Show Message Options" the Encrypt this message (S/MIME) & Digitally sign this message (S/MIME) are grayed out so I can't select them. I have no problem reading encrypted emails when someone sends to me. I do have a valid domain User certificate that has email encryption enabled. This did work fine on my previous version of exchange.
The odd thing is my Admin account mailbox which was used during the setup process is able to send encrypted emails to users. The options are available for that account.
Before I start moving everyone over to the new exchange I need to iron out this encryption so any suggestions. Was there something that I missed in my S/MIME configuration?
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