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Alternate Eudora Setup for SSL, Failing passwords and Relaying Denied Issues, SSL for Macintosh Eudora

Support: Email: Alternate Eudora Configuration

This setup is designed to help people having trouble getting Eudora to accept SSL Certificates. This is an "alternate" to the standard Eudora setup. Please read that document thoroughly before using this alternate how-to.

Password/Relaying Denied

SSL Fails After Upgrading Eudora

If you're having trouble sending mail using Eudora 5.1.1, 5.2+ or 6.0+, you may need to modify your Eudora settings to get it to work properly. Try the following steps:

STEP 1. Make sure your account is active. A disabled account, whether for nonpayment, account termination, etc. will disallow sending email.

STEP 2. Make sure you are using the correct password.

  • If you're 100% sure you are, log into your account at Cotse.Net, click Options, then change your password.
  • Once you've changed your password, go into Eudora Options, Checking Mail, uncheck "Save Password" (if you had it checked).
  • Shutdown Eudora and then reopen it.
  • Click "Check Mail" and enter the new password.
  • Once this is done, attempt to send a test message.

If you are able to send a test message, your problem is solved. If not, continue on to the next step.

STEP 3. If you're using an anti-virus program such as Norton or McAfee, these two a/v products are known to run a pseudo mail server on your machine. They're known to somewhat modify your mail settings and make changes to how your mail client behaves.

First, try turning the a/v off and sending a test message. If it works with non-SSL but not SSL continue to the next steps below.

STEP 4. If you're running a personal firewall, such as ZoneAlarm, try turning it off. You may want to do this and repeat Step 3 also. Personal firewalls can interfere with mail communications. Refer to your firewall documentation to learn how to eliminate this issue. A combination of the two can also cause trouble, therefore, the recommendation to attempt to turn off each, in sequence or each after turning off the firewall could perhaps resolve your trouble.

Eudora versions above 5.1 have a problem with SSL and your password. The following will attempt to resolve the known issue of SSL negotiation failing after upgrading to Eudora 5.2 when it had worked successfully with Eudora 5.1.

You can resolve this issue by making Eudora go back to the way Eudora 5.1 was handling SSL by using the settings listed below.

Find your OS and whether you're using standard port for SMTP (Port 25) or alternate port. Then compose a new email in Eudora. Copy and paste the appropriate text into the body of the email. The text will appear in blue as a URL. Hold down the ALT key and click on the URL.

Windows

To go back to the previous (5.1 behavior):

If you are using standard port for SMTP:
<x-eudora-option:SSLReceiveVersion=6>
 <x-eudora-option:SSLSendVersion=6>
 
If you are using alternate port for SMTP:
 <x-eudora-option:SSLAltPortReceiveVersion=6>
 <x-eudora-option:SSLAltPortSendVersion=6>

To restore the current (5.2 behavior):

If you are using standard port for SMTP:
 <x-eudora-option:SSLReceiveVersion=0>
 <x-eudora-option:SSLSendVersion=0>
 
If you are using alternate port for SMTP:
 <x-eudora-option:SSLAltPortReceiveVersion=0>
 <x-eudora-option:SSLAltPortSendVersion=0>

Macintosh

Copy and paste the text into a new message in Eudora and double click on the resulting URL:

To go back to the previous (5.1 behavior):

If you are using standard port for SMTP:
<x-eudora-setting:32456=768>
 
If you are using alternate port for SMTP:
<x-eudora-setting:32457=768>

To restore the current (5.2 behavior):

If you are using standard port for SMTP:
<x-eudora-setting:32456=769>
 
If you are using alternate port for SMTP:
<x-eudora-setting:32457=769>

SSL Certificate Issues

For Macs running MacOS 8.x-9.x:

First, make sure you're using the newest Cotse certificates. Go into the settings for SSL, delete/add the certificate that is up to date. Our certificates should all be current. If you're using an older certificate, you will have trouble.

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," "If Available Start TLS," or "Required, Start TLS" from the dropdown list.
  • Click OK.  

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," "If Available Start TLS," or "Required, Start TLS" from the dropdown list.
  • Click OK.

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. When you get that error message:

  • Go to Tools --> Options, and choose "Checking Mail" and/or "Sending Mail" items, as appropriate.
  • Click on "Last SSL Info". You should see info about the last failed attempt between your Eudora and the Cotse 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.
  • Highlight the server certificate and click on the "Add to Trusted" button.
  • Click "Done".

The next time you try to use Eudora to receive/send messages, using SSL, it should work OK.

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.)

From Eudora's menu bar, choose Special --> Settings.

Scroll down to/select the SSL item; a dialog box appears.

In the Personalities field, choose the desired personality from the popup menu (generally this will be "Dominant").

In the SSL for POP field, choose "Required, Alternate Port," "If Available, Start TLS," or "Required, Start TLS" from the popup menu. (This assumes that you have configured Eudora to use the POP protocol, which is the default.)

In the SSL for SMTP field, choose "Required, Alternate Port," "If Available Start TLS," or "Required, Start TLS" from the popup menu.

At this point, if you try to Check Mail (File --> Check Mail, or command-key plus "m"), you'll get the a message:

Click on "Open".

You'll get another message:

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

Make sure to lock your keychain, and exit the Keychain Access control panel.

You should now be able to send/receive messages securely between your computer and the Cotse server using Eudora & SSL.


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