Greetings,
I have a weird Problem. My Mailbox is hosted by a Provider with hosted Exchange 2013. I have a couple of customers who have their own mailboxes in their own Exchange 2007 organization. To enable S/MIME encrpytion, I have sent signed mails to them, they answered with signed mails. I have exported their X.509 certificate, have created an Outlook contact for each of them and have been carefully importing the certifcate to each contact.
So far so good. Everything should be in line now to enable S/MIME encryption. BUT:
- I cannot send encrypted mails when composing an new mail and choosing the recipient(s) from my Outlook contacts.
- I cannot encrypt the answer to a clear text mail.
- I cannot encrypt the answer to an encrpted, but not signed mail.- I can ONLY encrpyt when I reply to a signed mail.
I am on Windows 8.1 Professional 64 Bit. I run Office 2013 64 Bit. I use an S/MIME certificate from cacert.org.
Any ideas would be highly appreciated. Thanks a lot in advance for your help!
Paulette Feller
PS: in the meantime, I have tried the same procedure on a second Notebook, with Windows 8.1 Pro 64 Bit und Outlook 2013 32 Bit. I got exactly the same results. Can only encrypt when replying to signed Messages. Cannot encrypt new Messages, answers to encrypted (but not signed) Messages and answers to clear text (unsigned, unencrypted) Messages.
PPS: I installed Outlook 2010 64 Bit in parallel - same results :-( In will give a try to a virtual Win7 machine, though...
PPPS: also: no difference between Outlook Cache mode and Outlook online mode