Can't get mailhop.outbound.org secure SMTP server to work from Eudora - I'm switching to Thunderbird.

[Watermole]

I have an outbound mailhop account with www.dyndns.com which offers
secure authenticated SMTP relay on several ports. I cannot get the SMTP
server to accept my mail when sent from Eudora (I have tried all 3 SMTP
ports they offer). It works from Outlook Express (but not flawlessly),
but works beautifully from Mozilla based e-mail clients (Netscape mail,
Mozilla Mail and Thunderbird). In Thunderbird,it works with "TLS" but
not with "SSL".

The Eudora error message is:-

! Relay Personality, SSL:1 message left to send., RCPT
TO:<***@my.isp> [02:33:57 PM]
Cant send to ". The server gives this reason: '550 You must authenticate
to use Mailhop Outbound'.

Does anyone else have any problems with this server? What is the
difference between TLS and SSL and is this the problem?

[c***@iname.com]

On Wed, 26 Jan 2005 14:43:40 +1000, Watermole

Post by Watermole
Cant send to ". The server gives this reason: '550 You must authenticate
to use Mailhop Outbound'.

This usually means you need to download from "the"
POP3 server before sending with the SMTP server.

[Katrina Knight]

Post by Watermole
I have an outbound mailhop account with www.dyndns.com which offers
secure authenticated SMTP relay on several ports. I cannot get the SMTP
server to accept my mail when sent from Eudora (I have tried all 3 SMTP
ports they offer).
The Eudora error message is:-
! Relay Personality, SSL:1 message left to send., RCPT
Cant send to ". The server gives this reason: '550 You must authenticate
to use Mailhop Outbound'.

Do you have authentication turned on? Authentication uses the user ID and
password from the pop server to log into the smtp server too. That means
that the personality you're using, or the relay personality if you're
using one, has to have the correct information there. It looks like you're
probably using a relay personality. Do you have authentication turned on
in that relay personality and if so, have you given it the correct
password? You may need to check mail once with that personality to force
it to ask for the password.

Post by Watermole
Does anyone else have any problems with this server? What is the
difference between TLS and SSL and is this the problem?

SSL stands for "Secure Sockets Layer" and TLS stands for "Transport Layer
Security". In simple terms, TLS is a way of doing SSL. Eudora offers two
choices for the type of SSL to use - StartTLS or the older, alternate port
method. You do need to know which to tell it to use. What settings are you
using for outgoing SSL for the personality in question?

The error you're getting indicates that it is a problem with the server
needing authentication to know that you're an authorized user, rather than
it being an SSL problem. (There may actually be a problem with the SSL,
but that's not what the error is saying. Servers have been known to say
one thing when something else is really the root cause of problem.)

[Watermole]

Post by Katrina Knight
Do you have authentication turned on? Authentication uses the user ID and
password from the pop server to log into the smtp server too. That means
that the personality you're using, or the relay personality if you're
using one, has to have the correct information there. It looks like you're
probably using a relay personality. Do you have authentication turned on
in that relay personality and if so, have you given it the correct
password? You may need to check mail once with that personality to force
it to ask for the password.

Thx Katrina. Yes Allow Authentication is turned on in the options, I am
using a relay personality (although I have tried using it directly from
some accounts), the login username is correct (including case) and the
password is correct.

I have tried all 4 secure sockets options (Never; If Available STARTTLS;
Required, Alternate Port; and Required, STARTTLS) for each of the
available SMTP ports (25, 2525 and 10025) which I've correctly set in
Tools/Options/Ports.

The server is only an SMTP server (set up specifically to allow
authenticated relaying on alternative SMTP ports from sites where Port
25 is blocked). Hence one can't POP before send. In any case, sending
works from Mozilla mail clients (Netscape Mail and Thunderbird) when
TLS, but not SSL, is selected and when using the exact same settings as
I use in Eudora.

Still no go in Eudora!

[Katrina Knight]

Post by Watermole
Thx Katrina. Yes Allow Authentication is turned on in the options, I am
using a relay personality (although I have tried using it directly from
some accounts), the login username is correct (including case) and the
password is correct.

It needs to be turned on in the properties of the personality involved,
unless the personality is "dominant". If it is "dominant", then doing it
at Tools | options is fine. Have you checked to make sure it is indeed
turned on in your relay personality's properties?

Post by Watermole
I have tried all 4 secure sockets options (Never; If Available STARTTLS;
Required, Alternate Port; and Required, STARTTLS) for each of the
available SMTP ports (25, 2525 and 10025) which I've correctly set in
Tools/Options/Ports.

Can you find what out anything about what your SSL settings should be? If
SSL is needed, then obviously, "never" is wrong. The "if available" and
"required" StartTLS settings should have the same results if it is
available. The real question would seem to be whether what you should be
using is StartTLS or alternate part. From what you've said, my guess is
StartTLS. The other question would be whether you actually have the port
set correctly? The setting at Tools | options | ports sets it for the
dominant personality and any others that don't have it set specifically in
eudora.ini. If this isn't the dominant personality, is there any chance
that there is a setting for the port in eudora.ini that you're forgetting
about? Also, the port for alternate port SSL is set in eudora.ini using a
different settings - SSLSMTPAlternatePort. There are a bunch of SSL
settings that can go in eudora.ini.

Post by Watermole
The server is only an SMTP server (set up specifically to allow
authenticated relaying on alternative SMTP ports from sites where Port
25 is blocked). Hence one can't POP before send.

That doesn't follow, unless the service provider in questions doesn't
provide a POP server at all. The idea behind POP before SMTP is that the
system keeps track of whether you've recently logged into the pop server
from your IP address. If you have, then it assumes that the person logging
into the SMTP server from the same IP address is still you. I would expect
a server specifically set up to allow authenticated connections to be
using password authentication, but it is possible that it is indeed using
POP before SMTP. It would be worth trying if you haven't already tried it.
Just do a mail check for that account immediately before trying to send
messages.

[Watermole]

Post by Katrina Knight
It needs to be turned on in the properties of the personality involved,

Yes, done all this!

Post by Katrina Knight
Can you find what out anything about what your SSL settings should be? If
SSL is needed, then obviously, "never" is wrong. The "if available" and
"required" StartTLS settings should have the same results if it is
available.

Should be 'required', but 'if available' should work as well as you say.
It doesn't.

Post by Katrina Knight
The other question would be whether you actually have the port
set correctly? The setting at Tools | options | ports sets it for the
dominant personality and any others that don't have it set specifically in
eudora.ini. If this isn't the dominant personality, is there any chance
that there is a setting for the port in eudora.ini that you're forgetting
about?

This could possibly be the reason! :-) SSL by default operates on port
995 but mailhop.outbound.org operates on ports 25, 2525 or 10025.
Dominant is not using the SSL SMTP server but I do try to relay through
the relay personality occasionally.

Post by Katrina Knight
Also, the port for alternate port SSL is set in eudora.ini using a
different settings - SSLSMTPAlternatePort. There are a bunch of SSL
settings that can go in eudora.ini.

I will try this and see what happens. In any case, it seems to me to be
a pretty silly omission by Eudora authors not to enable port selection
for individual accounts from within the properties setting dialogs -
even if this needed to be activated for advanced users by setting a
check box somewhere in options. If Mozilla Mail can do it, so can
Eudora! Manually editing .ini files is dark ages stuff!

Post by Katrina Knight
That doesn't follow, unless the service provider in questions doesn't
provide a POP server at all.

That's exactly right. It is an SMTP server only to enable relay of
outbound mail (see http://www.dyndns.org/services/mailhop/outbound/ for
info) via secure sockets on a range of ports (see above). This allows
users to send mail from sites that can't relay through their normal
ISP's SMTP server because port 25 is blocked (eg my wife's workplace!).
This is common in a lot of commercial organisations - particularly
those running MS-Exchange servers.