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blank Notes on setting up SSL (Secure Sockets Layer) in Eudora 5.2
SSL is used for secure access to chemistry's mail server, especially from outside the Department.

This assumes you've already downloaded/installed the Eudora 5.2 software (from OIT's Software-to-Go site at http://osusls.osu.edu) & have the basic configuration to access the chemistry server already set up. See the following FAQs for more information:

How do I configure Eudora properly?
How can I access my email from outside the Department?
The Great SSH Primer

For PCs running Windows 95/98/ME/NT 4.0/2000/XP:

Applies to either POP- or IMAP-type setups.

  1. To use Secure Sockets when Receiving messages:
    • Go to Tools->Options, and choose the "Checking Mail" item from the column on the left.
    • In the section "Secure Sockets when Receiving", choose "Required, Alternate Port" from the dropdown list, then click "OK".

  2. (OPTIONAL) To use Secure Sockets when Sending messages:
    • Go to Tools->Options, and choose the "Sending Mail" item from the column on the left.
    • In the section "Secure Sockets when Sending", choose "Required, Alternate Port" from the dropdown list, then click "OK".

  3. The first time you try to use Eudora with SSL features, you will likely receive an error message similar to the following:

    "SSL Negotiation Failed: Certificate Error: Cert Chain not trusted. Try adding this certificate database for SSL to succeed. Unknown certificate chain validation error..."

    This is normal. To deal with it:

    • Go to Tools->Options, and choose "Checking Mail" &/or "Sending Mail" items, as appropriate, and click on "Last SSL Info". You should see info about the last failed attempt between your Eudora and the chemistry server.
    • Click on "Certificate Information Manager". In the "Server Certificates" section at the top of the screen, you should see the server certificate involved with a skull image to the left of it; you may click on the "View Certificate Details" for further info if you wish. With the server certificate highlighted, click on the "Add to Trusted" button. Then click on "Done".
    • The next time you try to use Eudora to receive/send messages, using SSL, it should work OK.
For Macs running MacOS 8.x-9.x and MacOS 10.2 (Jaguar) or later:

To use SSL in Eudora for Macs, you must have Apple's "Keychain" installed on your computer. (Note: Eudora's SSL feature is not yet supported under Mac OSX.)

  1. From Eudora's menubar, choose Special->Settings…
  2. Scroll down to/select the SSL item; a dialog box appears.
  3. In the Personalities field, choose the desired personality from the popup menu (generally this will be "Dominant").
  4. In the SSL for POP field, choose "Required (Alternate Port)" from the popup menu. (This assumes that you have configured Eudora to use the POP protocol, which is the default. If you have configured Eudora to use the IMAP protocol instead of the POP protocol, you may leave the SSL for POP field set to "None".)
  5. (OPTIONAL) In the SSL for SMTP field, choose "Required (Alternate Port)" from the popup menu.
  6. In the SSL for IMAP field, leave the setting pointed to "None" unless you have configured Eudora to use the IMAP protocol instead of the POP protocol. In that case, choose "Required (Alternate Port)" from the popup menu for this field.
  7. At this point, if you try to Check Mail (File->Check Mail, or command-key plus "m"), you'll get the following message:
  8. eudora message

    Click on "Open".

  9. You'll get another message:
  10. eudora message

    Click on "Add to keychain", then "OK", and in the next box, click on "Done". The certificate has been added to your keychain.

  11. Make sure to lock your keychain, and exit the Keychain Access control panel.
  12. You should now be able to send/receive messages securely between your computer and the chemistry server using Eudora & SSL. This eliminates the need to tunnel Eudora through a SSH client to access the mail on your chemistry account from a computer running Eudora outside the Department.
For Macs running MacOS 10.0-10.1.5:

Since Eudora 5.2 does not support SSL for MacOS 10.0-10.1.5, and a secure connection is needed if you want to access your email from outside the Department, you may wish to upgrade your operating system to 10.2. Otherwise, if you'd like to use the native MacOSX version of Eudora 5.2 (in lieu of using the Mac Classic version of Eudora w/SSL and running Classic Environment), here's a way to do it.

Setting up port forwarding using Mac OSX's built-in ssh software & Eudora (using POP protocol):

  1. On Mac, run "Terminal" utility (normally found in a folder called "Utilities" inside your MacOSX "Applications" folder)..
  2. At the command prompt, type the following, followed by a return:

    sudo ssh -l username -L25:chemistry.ohio-state.edu:25 -L110:chemistry.ohio-state.edu:110 -N chemistry.ohio-state.edu

    where "username" is the userid for your chemistry Unix account.

    At the prompt "Password:", enter the password for your Mac OSX user account (you must be logged onto your Mac as a user with administrator privileges).

    You'll then be prompted for the password for your account on chemistry.ohio-state.edu. Enter that and press return.

    Leave your terminal session running.

  3. In the Eudora settings (in Eudora 5.2, go to Special --> Settings...) in the Getting Started item, "Checking Mail" section, change the entry for "Mail Server" to "localhost" (minus the quotes), and in the "Sending Mail" section, change the entry for "SMTP Server" to "localhost", then click "OK".
  4. You may need to exit Eudora and then restart it for the new settings to take effect.
  5. When you restart Eudora, you should be able to send/receive mail securely.
  6. When you done, quit Eudora, and quit your Terminal session.

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