How do I fix Eudora SSL certificate problems?

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With some versions of Eudora, you may receive an error message that says something like this:

SSL Negotiation Failed: Certificate Error: Cert Chain not trusted. Try adding this certificate to your certificate database for SSL to succeed.

This happens because Eudora has not been updated for a long time, and does not include modern "SSL root certificates" needed to encrypt your email messages.

You should be able to use the instructions below to add the necessary SSL certificate to Eudora.

1. Make the error happen.

In order for the instructions below to work, you need to have seen the error since you started Eudora. Send a test message to make the error happen.

2. Open the Eudora options window.

Click Tools, then Options from the menu bar.

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3. The Options window appears.

Click Sending Mail in the category list, then click the Last SSL Info button.

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4. The Eudora SSL Connection Information Manager window appears.

Click Certificate Information Manager.

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5. The Certificate Information Manager appears.

Make sure that the tigertech.net certificate (located under server certificates) is highlighted, then click Add To Trusted. (It may list the name as "mail.tigertech.net", "*.tigertech.net", or something similar.)

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The certificate will be added and appear under the User Trusted Certificates

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Click Done to close the Certificate Information Manager window, then OK to close the Eudora SSL Connection Information Manager and OK to close the Options window.

Eudora should now be fully configured. Try sending yourself a test message.

What if the instructions above don’t work?

We’ve heard of a few cases where clicking the Last SSL Info button in step 3 doesn’t show any certificates, instead telling you that you haven't had any SSL failures with the current “personality”.

If this happens to you, the simplest thing to do is just turn off the SSL for outgoing connections:

  • Under “Secure sockets when sending”, select Never
  • If your version of Eudora has a Use submission port (587) checkbox, check it.

If you still can’t send and your copy of Eudora doesn’t have a “Use submission port (587)” checkbox, choose Ports in the category list and change the SMTP port from “25” to 587.

This should make Eudora avoid using SSL to send mail. If you’re wondering if this is insecure, the answer is that it’s no more insecure than Eudora already is, because Eudora doesn’t use SSL for incoming mail anyway. It’s already sending your password without SSL every time you read mail. If this bothers you (it should), we recommend switching to a modern, free, SSL-capable program like Mozilla Thunderbird.