One more question on S/MIME, please:
while sending encrypted message from user 1 (Shannon Emma) to user 2 (Taylor David - and Taylor's certificate is installed on the workstation) I get the following warning:
- here Outlook on the WEB "thinks" that Shannon Emma is the recipient that doesn't have the corresponding certificate while Emma is the SENDER, NOT the recipient!
...maybe Outlook on the Web names Shannon Emmas as a recipient because this message may be read in the Shannon's Sent Items folder and in this context she'll be the "recipient"...?
2) this page says:
"If you encrypt an outgoing message and Outlook on the web can’t verify that all recipients can decrypt the message, you’ll see a notice warning you which recipients might not be able to read the encrypted message. You can then send the message anyway, remove those recipients, or retry to check again."
Q2: A recipient would be able to descrypt the message if he/she has the corresponding private key on his/her workstation - how Outlook on the Web on the sender's computer is supposed to check the availability of the private key on the recipient's computer?