encryption problems

[racimodeoro]

One of my users wants to send encrypted emails to 15 members outside the
company once every quarte to send reports. I wanted to test Outlook's
functionality to encrypt and digitally sign emails before purchasing digital
certificates recommended by Microsoft. So I recently obtained my personal
digital cert to encrypt messages using Outlook 2007.
I sent an email with my digital Id to the user, upon receipt he added me on
her Contact List.
When I sent another email and encrypted the message changing Message Options
Security settings to"Encrypt message contents and attachments" I got the
following dialog box:
Encryption Problems: Microsoft Office Outlook had problems encrypting this
message because the following recipient had missing or invalid certificates,
or conflicting or unsupported encryption capabilities:
(e-mail address removed)
Continue will encrypt and send the message but the listed recipient may not
be able to read it. Send encrypted button Continue (grayed out) Cancel

Please advise. Thank you.

 

[Brian Tillman]

One of my users wants to send encrypted emails to 15 members outside
the company once every quarte to send reports. I wanted to test
Outlook's functionality to encrypt and digitally sign emails before
purchasing digital certificates recommended by Microsoft. So I
recently obtained my personal digital cert to encrypt messages using
Outlook 2007.
I sent an email with my digital Id to the user, upon receipt he added
me on her Contact List.
When I sent another email and encrypted the message changing Message
Options Security settings to"Encrypt message contents and
attachments" I got the following dialog box:
Encryption Problems: Microsoft Office Outlook had problems
encrypting this message because the following recipient had missing
or invalid certificates, or conflicting or unsupported encryption
capabilities:
(e-mail address removed)
Continue will encrypt and send the message but the listed recipient
may not be able to read it. Send encrypted button Continue (grayed
out) Cancel

In order to encrypt a message, you do not need a certificate. The person
with whom you are corresponding, however, does. Two-way Public Key
Encryption requires that you BOTH have certificates and that you send
digitally-signed messages to each other. When you send a digitally-signed
message, you are sending your public key and it is with that public key that
your correspondent will be able to send YOU an encrypted message. You will
not be able to send them an encrypted message until they get a certificate
and send you their public key via a digitally-signed message.

 

[racimodeoro]

In order for me to encrypt future email messages, my user will also need to
obtain their own digital ID certificate and send me a digitally-signed
messages in order for this encryption to work..am I correct in my assumption?

Is there any easier way for the 15 users (who are not really tech-savvy
regarding encryption) who will be receiving the quarterly reports avoid this
process of obtaining their own digital IDs?

Thank you for your prompt response.