Changing Ports Used by Eudora

You can change the ports used by Eudora for outgoing or incoming email from the standard SMTP and POP3 ports, which are 25 and 110, respectively. To do so, close Eudora then move the esoteric.epi file from Eudora Pro\extrastuff up one directory to Eudora Pro, presuming that you installed Eudora in \Program Files\Eudora Pro. Then take the following steps:

1. Click on Tools.
2. Scroll down to Ports.
3. You can then put in a port number, e.g. 587 in the SMTP field, so that Eudora would connect to port 587 on the SMTP server rather than the default port of 25.
4. Click on the OK button.

Note: tested with Eudora 4.2.2

References:

1. Esoteric.epi / Esoteric Settings (Windows)
   Eudora
2. Changing Ports for Sending/Receiving (Win)
   Eudora

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Eudora and SMTP AUTH

Many email servers require senders to authenticate with the server by some mechanism, such as by providing a userid and password, when attempting to send email through the email server that is not destined for an email address residing on the server itself.

If you are attempting to send an email message using Eudora and you see a message similar to the one below, then the SMTP server that Eudora has been configured to use for outgoing email likely requires authentication.

Can't send to 'someone@example.com'. The server gives this reason: '550 5.7.1
<someone@example.com>... Relaying denied. Proper authentication required.'.

Version 4.2.2 of Eudora supports authentication when sending email. If you have a Windows 4.x version of Eudora, you can upgrade it to version 4.2.2 by downloading ep4xto422.exe from the updater422 folder on the Qualcomm FTP site. Version 4.2.0 doesn't support authenticating when sending email, though the help files indicate that it does, according to Eudora Pro 4.x - SMTP Auth . If you don't know which version of Eudora you are running, you can click on Help and then About in Eudora. You should see "Version 4.2.2" for that version.

To enable authentication when sending in Eudora 4.2.2, you must edit the eudora.ini file. Close Eudora, if it is open, and add the following two lines below the [Settings] line in eudora.ini file.

SMTPAuthRequired=1
SMTPAuthAllowed=1

Then, when you reopen Eudora, SMTP authorization should be enabled.

Note: there are different methods of authenticating with an email server. If you see a message similar to the following, the email server does not support the authentication method used by Eudora.

<Dominant>, Connecting to the Mail Server..., [05:24:13 PM]
Can't find a supported authentication mechanism for sending messages, and you've
specified to require authentication.

For instance, Eudora 4.2.2 doesn't support the Plain and Login methods.

You can determine which authentication methods a server supports by using telnet to connect to port 25 on the server, which is the standard SMTP port. After you issue an HELO or EHLO command and some name for the system from which you are connecting, e.g. "laptop" or "mysystem.example.com", you should see AUTH listed as one of the commands the server understands with the authentication methods it supports listed immediately after AUTH on the same line.

telnet 127.0.0.1 25
Trying 127.0.0.1...
Connected to localhost.localdomain (127.0.0.1).
Escape character is '^]'.
220 example.com ESMTP Sendmail 8.13.8/8.13.8; Sun, 11 May 2008 17:28:54 -0400
ehlo laptop
250-example.com Hello localhost.localdomain [127.0.0.1], pleased to meet you
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-8BITMIME
250-SIZE
250-DSN
250-ETRN
250-AUTH LOGIN PLAIN
250-DELIVERBY
250 HELP

In the example above, the email server only supports the LOGIN and PLAIN methods, which resulted in Eudora complaining that it "Can't find a supported authentication mechanism for sending messages, and you've specified to require authentication."

According to Negotiating an SMTP AUTH Authentication Mechanism, "The standard Eudora client (downloadable from www.eudora.com) tries to use CRAM-MD5 by default."

If an email server supports CRAM-MD5 and DIGEST-MD5, you would see the following, if you connected to port 25 on the server, after you issued an helo or ehlo command..

250-AUTH DIGEST-MD5 CRAM-MD5

References:

1. Eudora Pro 4.x - SMTP Auth
   jellico.com, Inc.
2. Negotiating an SMTP AUTH Authentication Mechanism
   By Weldon Whipple
   Technoids.org

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