> Just a point of clarification... port 465 isn't "deprecated" because it was 
> never formerly assigned by IANA.
>
> It was highjacked by some mailer (I forget which) and when 587 was assigned, 
> it was agreed to stop using the former port.
>
> As for one of your questions, it's assumed that 465 comes up with SSL turned 
> on by default, and that it doesn't come up in the clear with STARTTLS turning 
> TLS on.
>
> And "plain" sends the password in the clear, but "login" sends it hashed. 
> I.e. you need:

I'm OK to send the password "in the clear" since the entire connection
is encrypted from STARTTLS, correct?

> pwcheck_method: saslauthd
> mech_list: plain login
>
> in your /etc/sasl2/smtp.conf file... or you can change "mech_list" to only 
> "login", or even "digest-md5" and "cram-md5" (as we do here) with TB using 
> "Encrypted password" as the authentication type.

You found a typo in my /etc/sasl2/smtpd.conf which I've corrected and
I no longer get the "Bad sequence of commands 503 5.5.1 Error:
authentication not enabled" error from Squirrelmail when I specify
port 25, but Squirrelmail still won't send mail over 25 or 587.

- Grant


>> I've been using smtps on port 465 for sending mail but I read it's
>> deprecated so I'm trying to switch to submission port 587.
>>
>> With 465 I was using the "Connection security: SSL/TLS" setting in
>> Thunderbird, but after switching to 587 I can't send mail unless I
>> change it to STARTTLS.  Can anyone explain this?  Should I be using
>> STARTTLS instead of SSL/TLS for courier 993?
>>
>> Whether using 465 or 587, I noticed I can't log in to send mail from
>> my mail clients unless the password is sent unencrypted.  Is that OK
>> since I'm using STARTTLS or should I also enable encryption of the
>> password?
>>
>> Previously in master.cf I was running smtps like this:
>>
>> smtps     inet  n       -       n       -       -       smtpd
>>   -o smtpd_tls_wrappermode=yes
>> #  -o smtpd_sasl_auth_enable=yes
>> #  -o smtpd_client_restrictions=permit_sasl_authenticated,reject
>> #  -o milter_macro_daemon_name=ORIGINATING
>>
>> Should I enable all of this for submission:
>>
>> submission inet n       -       n       -       -       smtpd
>>   -o smtpd_tls_security_level=encrypt
>>   -o smtpd_sasl_auth_enable=yes
>>   -o smtpd_client_restrictions=permit_sasl_authenticated,reject
>>   -o milter_macro_daemon_name=ORIGINATING
>>
>> I don't think I need milter_macro_daemon_name since I'm not using a
>> mail filter.  I am running saslauthd but it looks like I didn't have
>> it enabled for smtps previously.  I'm surprised because I thought I
>> required authentication in order to use smtps.
>>
>> Here is most of the non-default stuff from main.cf:
>>
>> smtpd_sasl_auth_enable = yes
>> smtpd_sasl2_auth_enable = yes
>> smtpd_sasl_security_options = noanonymous
>> smtpd_sasl_local_domain =
>>
>> smtpd_recipient_restrictions =
>>         permit_sasl_authenticated,
>>         permit_mynetworks,
>>         reject_unauth_destination,
>>         permit
>>
>> postscreen_greet_action = enforce
>> postscreen_pipelining_enable = yes
>> postscreen_pipelining_action = enforce
>> postscreen_non_smtp_command_enable = yes
>> postscreen_non_smtp_command_action = enforce
>> postscreen_bare_newline_enable = yes
>> postscreen_bare_newline_action = enforce
>>
>> smtpd_tls_security_level = may
>> smtpd_tls_auth_only = yes
>>
>> Thanks to anyone who can help me out with this or point out any
>> deficiencies/stupidities in my config.
>>
>> - Grant

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