> -----Original Message-----
> 
> 1.       end-2-end encrypted emails for managed users registered with the
> same email domain (internal users). From the docs I understand that either
> PGP or S/MIME is used.
>

If your internal users are using the same e-mail system then e-mails between 
them most likely won't even hit the ciphermail gateway to even perform any type 
of encryption.


> 2.       For the internal users to send secure email to any other external
> email address (other domains). From the docs I understand that WebMail or
> PDF is used.

The options to send e-mail from internal to external are encrypted PDF, S/MIME 
and PGP


> 
> 3.       Simple remote installation/setup and users' usage (people with 0
> tech capabilities).

S/MIME for sure will require some basic knowledge of using the PC in order to 
install certs on their PCs. I haven't used PGP but I understand that it 
functions very similar to S/MIME. In my experience using ciphermail on customer 
installation is as follows:

If there are external users that you internal customer will be e-mailing on a 
regular basis and those e-mail must be encrypted, you would set those external 
users in ciphermail beforehand with mandatory encryption. I would recommend PDF 
encryption with a static password that you give those external users. If you 
want to go the route of S/MIME or PGP you will have to get involved with 
installing/configuring certs on those users PCs if we are talking about users 
with little or no tech experience. I've done it before and it's a pain. Biggest 
issue I've ran into is the expectation for the external users to be able to 
encrypt back to my internal users. Ciphermail will handle that but the external 
user has to be able to remember to encrypt those e-mail using s/mime or PGP 
from their end using their e-mail client (outlook etc...). 





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