**IGNORE THIS QUESTION - SOLVED WITH A PYTHON SCRIPT available at: http://yabahaus.blogspot.com

I have to connect one customer Outlook 2010 to a remote server on which I have either no right, neither way to talk to the sysadmin. This is the thing, after installing and reviewing the logs on Wireshark:

Outlook Express:

HELO machine
AUTH LOGIN
username base64 encoded
password base64 encoded
mails go through.

Outlook 2010:

HELO machine
AUTH DIGEST-MD5
response from server
Outlook sends just a *
AUTH LOGIN
password base64 encoded

So... I can send mails in the same domain, but can't send outside, it gives me a relay denied message. My point is... Why the h**l Outlook 2010 doesn't send the username AND the password?! It can never login the right way :| With other versions of Outlook it works fine, and with OE works great, it auths and allows to send mail to a different domain. I've googled and nothing worked. I'm pretty sure that I'm not alone with this one. My last resort will be to configure a local proxy/server that relays to the original one :| Any help would be appreciated. Sorry my bad english as is not my natural language. Thanks.

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please post your answer using the Answer your question button below. – Ben Pilbrow Feb 24 '11 at 18:28
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1 Answer

Usually this is caused by outlooks "Outgoing Server Requires Authorization" not being checked.

Should be under Tools > Account Settings > (select account) > Advanced > Outgoing Server.

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Yes. It is. I used the same config at OE and O2010 – Filipe YaBa Polido Jan 13 '11 at 22:06
The problem is that O2010 want to use DIGEST-MD5 even if it fails. – Filipe YaBa Polido Jan 14 '11 at 11:53
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