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From: "Lee Dilkie" <lee@dilkie.com>
To: "'Richard Stevenson'" <richard@endace.com>,
	"'Noah'" <admin2@enabled.com>
Date: Wed, 26 May 2004 07:22:19 -0400
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>On Tue, 25 May 2004, Noah wrote:
>
>> sendmail-8.12.11
>> freeBSD-4.9-STABLE
>>
>> I must be doing something wrong.  SMTP AUTH is not working=20
>very well for me.
>> I have been trying to authenticate with user and password to port 25.
>>
>> I prefer to send all auth user and password information with=20
>SSL encryption.
>> would like SSL Version 3 encryption.
>
>You've got "This server requires a secure connection (SSL)"=20
>enabled for=20
>the SMTP server in Outlook?

In my experience (outlook 2000, not tested on outlook express) this =
won't work. Outlook doesn't seem to understand that "use SSL" means "use =
STARTLS". What I did was to configure sendmail to also support "smtps" =
(SSL before SMTP) on the smtps port (465) and point outlook at that port =
with the "use ssl" checked.=20

>
>> I have configured outgoing mail requiring authentication=20
>then clicking both
>> with Secure Password Authenticaiton and without.
>
>That should be "without" for SPA.

Agreed, turn off SPA.

>

-lee