Using Outbound with Eudora

Using Outbound with Eudora for Mac OS X

This document describes how to configure Eudora for Mac OS X to work with MailHop Outbound.

Setting up an SMTP Relay Personality

The very first thing you need to do when configuring Eudora to send mail via Outbound is setup an SMTP Relay Personality.

Select the Personality panel in the Preferences. Create a new personality and name this MHO or Outbound or something similar. In the "User Name" field of the "Checking Mail" section, enter your DynDNS username and in the "SMTP Server" field enter outbound.mailhop.org (and optionally the desired port as described below).

Yes, you MUST enter your DynDNS username in the "Checking Mail" section, because this is what Eudora will use when performing SMTP authentication. Yes, this seems silly, but that's the way it is.

Make sure that "Use submission port (587)" is disabled and that "Allow Authorization" is checked.

The other fields can (and should) be left blank.

Now, select the Sending Mail panel in the preferences, and select the newly created personality as the SMTP Relay Personality. The "Use submission port" and "Allow authorization" options in this panel are ignored when an STMP Relay Personality is selected.

Once you have setup the SMTP Relay Personality, go to the Personality Extras panel and, for the «Dominant» and each additional personality, turn on the "Use relay personality, if defined" option.

Enabling SSL

MailHop Outbound does not require the use of SSL, but DynDNS STRONGLY recommends that you always use SSL when using this (or any other) SMTP server (when possible).

In the Eudora Preferences, select the SSL panel. Select the SMTP Relay Personality from the "Personality" popup menu. For the "SSL for SMTP" option, select either

If you select the first option, Eudora will use port 25 by default and will issue a STARTTLS command.

If you select the Alternate Port option, Eudora will use port 465 by default and initiate an SSL session.

Both of these options are equally secure and MailHop Outbound supports both.

This second option is commonly referred to as SMTPS, and is officially deprecated in favor of STARTTLS. However, MailHop Outbound does support this method and is expected to do so for the foreseeable future.

For both the Standard Port and Alternate Port sections, select either the "Maximum Compatibility" option or "TLS 1.0" (both work).

Both of these methods have been tested with Eudora and MailHop Outbound. However, you may find it necessary to use the second option if your ISP blocks outgoing connections on port 25 (as many do).

Using a port other than 25/465

If you can not use either port 25 or port 465, you can force Eudora to use a different port by appending a port to the name of the SMTP Server in the SMTP Relay Personality configuration. For example, to use port 2525 you would enter 

    outbound.mailhop.org:2525

When specifying port 25, 2525 or 10025 you need to either have SSL disabled or use the "Required (TLS)" option. When specifying port 465 or 10465 you must have SSL enabled and select the "Required (Alternate Port)" option.

Setting up Passwords

If you have Eudora setup to use the Apple Keychain, and you have entered an incorrect password, Eudora will fail to authenticate but won't prompt you for a new password. As of 6.2.3 there doesn't seem to be any way to clear this bad password from within the app (the Forget Password menu command appears to not do the trick).

In order to fix this you will have to open the Keychain Access application, find the associated key and either delete the key or change the password from within the Keychain Access app (you'll find this within Applications:Utilities in the Finder).

Using Outbound with Eudora (Windows)

You may use the following settings to correctly configure Eudora for Windows. Essentially, all SMTP settings must be cleared, except for the Outbound Settings under the Relayman personality. Under the Tools: Options: Sending Mail menu, select Relayman as the Relay Personality.

Dominant Personality

Real Name <Your Name>
Email Address <Your Email Address>
Username: <Your DynDNS Username>
SMTP Server (blank)
Authentication Allowed: (unchecked)
Use Relay Personality: (checked)
Secure Sockets While Sending Required, STARTTLS

Relayman Personality

Real Name: Relayman
Email Address: <Your Email Address>
Username: <Your DynDNS Username>
SMTP Server: outbound.mailhop.org
Authentication Allowed: (checked)
Use Relay Personality: (checked)
Secure Sockets While Sending: Required, STARTTLS
Check Mail: (unchecked)

Sending Mail (under Tools: Options):

Email Address: (blank)
SMTP Server: (blank)
SMTP Relay Personality: Relayman
All Options: (unchecked)
Secure Sockets While Sending: Required, STARTTLS

Troubleshooting

Some users report that using the same outbound and inbound mail server can remove some of the issues that arise in Eudora for Windows. Try setting both the Outbound and Inbound Mail Servers to outbound.mailhop.org