Eudora 5.1 IMAP-SSL SetUp
In order to configure Eudora to use IMAP-SSL,
there are two requirements.
First, Eudora must be configured to speak to
our IMAP-SSL server running on port 993.
Second, Eudora must be configured to accept
and trust the SSL certificate that is installed
on our IMAP-SSL server.
Let's deal with the former problem first.
A. Click on the "Tools" menu item.
B. Click on "Options"
C. Highlight the "Check Mail" icon in the left pane.
In the right pane, note their is a dropdown box
titled "Secure Sockets when Receiving". Here,
select the option "Required, Alternate Port".
This will configure Eudora to speak to port
993 for IMAP-SSL connections.
D. Click "OK"
E. Now, shutdown and restart Eudora51 (This is an important
F. After Eudora has restarted, click on the "Check Mail"
icon on the top menu bar. Depending on how you
configured Eudora, you might be prompted for your
password. Nonetheless, the authentication process
will fail. This is OK. Let it fail but do **not**
shut Eudora down again!
The reason it fails is because Eudora does not
trust our IMAP-SSL certificate. Now we need to
convince Eudora to trust our IMAP-SSL certificate.
The certicate is currently cached on the client
but it is treated as untrusted.
G. With Eudora still running, note the window pane
that is located on the left of Eudora's main
window. (It is almost directly below the "IN" and
and "OUT" tray icons).
There are five icons sitting right below this
Click on the icon that has two faces. This will trigger
the window to display "Persona" and "Account" inform-
ation. In my window, my "Persona" name is "".
Right click on your "Persona" name and select
"Properties". A new window pops up.
H. Click on the tab labelled "Incoming Mail".
I. Near the bottom of the window, you will see a button
titled "Last SSL info". Click on it. A new window will
pop up titled "Eudora SSL Connection Information Manager"
J. You should see in the "Notes" section, a warning message that
"Certificate Error: Cert Chain not trusted.
Try adding this certificate to your certificate database for
SSL to succeed".
K. Click on the button labelled "Certificate Information Manager".
A new window pops up.
L. Now, you should at the top section of this window, the cs
server certificate. It should be highlighted. It has a
little skull and cross bones next to it.
The certicate is titled:
"CA, Ontario, Toronto, "University of Toronto, CSLab..."
M. While the CSLab server certificate is highlighted, click the
button labelled "Add To Trusted". The skull and cross bones
icon will remain, but a "User Trusted Certicate" will now
be added to the top window. Click "Done"
N. Click OK. Click OK again.
0. Now you should be able to retrieve mail using IMAP-SSL
XX was attempting to use Eudora 5.1 and IMAP-SSL to retrieve his
email from imap.cs.toronto.edu. The login process was failing, as
confirmed by lack of IMAP messages in jane.cs:/var/log/mail
After some thought, determined that the problem was most likely that
A. Eudora's IMAP-SSL connections were hitting the wrong port or
B. Eudora was unable to process our IMAP-SSL certificate
Turns out it was a mixture of both.
A. Startup Eudora, click on Special, Settings, SSL, and
select for "SSL for IMAP" "Required (Alternate Port)"
B. In order to process digital certificates, MAC OS's require the existence
of a keychain. XX's laptop did not have one. Here are the instructions on
how to create one.
Part 1 (culled from: http://docs.info.apple.com/article.html?artnum=60482)
To create a keychain:
1. Open the Keychain Access control panel.
2. If a keychain doesn't already exist, you're asked if
you want to create one. Click Create. If a locked keychain
already exists, click Cancel, then open the File menu and
choose New Keychain.
3. Enter information for your new keychain and click Create.
Remember your password, because you'll need to re-enter it exactly to
use the keychain. To make your keychain more secure, be sure to choose
a good password.
Your keychain is stored in the Keychains folder in the Preferences folder
inside the System Folder.
Now when a Eudora IMAP-SSL sessions begins, the end user is prompted to accept the
cs.toronto.edu IMAP-SSL certificate. If they do accept it, they can then proceed.