Configuring IMAP-SSL and SMTP-SSL in Eudora 6.1 (Windows)
  Open Eudora, go the Tools menu and select Options... 
  
  Go to the 
Checking Mail section.
  
    - For “Secure Sockets when Receiving” choose “Required, Alternate Port ”

   
  NOTE: After testing, If you have problems with using "Required, Alternate Port", you should try using “Required, STARTTLS” to receive instead.
   
  Go to the Incoming Mail section. 
  
    - Make sure Cram-MD5 is selected for the Authentication style. 

   Go to the Sending Mail section. 
  
    - Make sure Allow authentication is checked.
 
- Change the Secure Sockets when Sending to Required, Alternate Port .
 
 
  
    
 When you are finished, click OK.
 
  In order to read and send mail securely, you will need to tell Eudora which SSL certificate to trust.
  Send a test message so that Eudora learns about the certificate. Send yourself a test message first (it will likely fail and put itself in the Outbox)
  Then, go back to the Tools menu and select Options... Go to the Sending Mail section. 
  
    - Click on the Last SSL Info button next to Secure Sockets when Sending to Required, Alternate Port 
- It will bring up the SSL Connection Information Manager. Click on the Certificate Information Manager 
- Click on Server Certificates
- Locate and select the certificate listed as "US, Equifax, Equifax Secure Certificate Authority" and under it "US, California, Santa Barbara, University of California Santa Barbara, Physics Department, smtp.physics.ucsb.edu"
- Click on Add to Trusted 
- Click OK to exit out
- Attempt to send your test message from the Outbox. It should now go out properly.