SMTP/SSL email sending problem with Entourage 2004 from T-Mobile Hotspot

M

Mike

Six months or so ago I resolved a problem that had been plaguing me
for months - sending email via Entourage from T-Mobile and other "hot
spots." The solution was that my ISP gave me an "SSL" code and I
configured email sending to use it, solving the problem of sending
from any location I came across. Upgrading to Entourage 2004
hasthrown me back into the morass. Somehow it does not allow me to
use the SSL. WIthout it, I can send fine from home and work, but at
"hot spots" I get the following message:
Authentication failed because Entourage doesn't support any of the
available authentication methods.
Ideas?
 
T

Timberfish

Well, I can't say this will offer much help, but I'm having the same
issue. From what I've learned through Google searches and speaking
with tech support (my ISP's) - it seems that t-mobile hotspots encrypt
all traffic in and out. This means that if you're ISP's SMTP server
requires a password to send (which mine does) then that pass will be
encrypted and not sent as plain text even though it will be sent as
plain text while at work or home. For my issue it seems that
MailEnable (my ISP's mail server) only allows unencrypted passwords and
Entourage doesn't support NTLM 1 (whatever that is) so the combination
results in this error.

As I said, this isn't much help since there's no solution. In fact the
solution I keep getting is to switch to the Apple Mail app. Yeah,
after spending $300 on Office, I want to use a free client when roaming.

Has anyone contacted Microsoft directly about this? It seems to be a
limitation in Entourage 2004 and there should be a workaround, but
either way I'm angry at the "loss" of compatability when upgrading from
Office X. Absurd.
 
T

Timberfish

Okay, now I have even more to add. I've tried setting up the same
email account in Apple Mail and I get another error message when at a
t-mobile hotspot. It's a bit different but I think it's the same issue
- here it is: The SMTP server “mail.timberfish.com†doesn’t support
authentication. Please check your account settings and try again.

Is anyone able to shed any light on this?
 
T

Timberfish

Okay, don't see that anyone else really cares about this thread, but
here's the final answer after much time and research. It's all
explained at this link:
http://www.mobilewhack.com/networking/wifi/beware_of_captive_smtp.html

Not only do you see a full explanation of the issue here, but you can
also see several posted solutions. I will resort to complaining to
T-mobile rather than these extensive workarounds. Good luck everyone.
 
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