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encrypted SMTPing with TheBat, TLS problems
 
#1
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so the problem basically is that TheBat fails to smtp through our TLS (regardless of using STARTTLS or TLS).

so saying that i am specified the following:

POP: _server_ - port: 995 - SSL - login/password
SMTP: server_ - port: 25 or 2525 - TLS - same login/password and a valid sender address

(a valid sender address means that the server will accept only the mail from certain addresses)

so how can i configure TheBat for it to work? i couldn't manage to do that, i just receive either "TLS protocol error: Unknown Message SessionUnknownContentType ct (50)" or "5.7.3 Client has no permission to submit mail to this server" while pop3 connection through TLS works perfect.
 
 
 
#2
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and one more thing: why TheBat doen't support SMTPing through SSL?
 
 
 
#3
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TB is supposed to run flawlessly with TLS, the default port for TLS is 465, are you sure you shouldn't use that?

As for your last question, I've always believed that SSL end TLS are two names for the same protocol, though some sources on the net are saying something else. However, when you've got POP3 over TLS running, I can't imagine that your server should use a different security protocol for SMTP (TB only offers TLS).
__________________________________
I'm just a user of The Bat! I don't work for Ritlabs.
 
 
 
#4
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the default port is the port that is specified by the server and not some abstract fixed port. our mail server has TLS configured over 25 and 2525 ports. and as thousand of other people can use TLS over those ports to send mails under outlook and thunderbird, then i can basically suppose that TB is not so flawless as you say :P.

and well it seemes that your beleif is wrong as even in TB SSL and TLS are different types of protocols for POP3 (you can easily see it when configuring the account).

anyway, that doesn't answer my questions: how come that TB works with secure POP3 and does not with SMTP given the same credentials (i am sure that there's something wrong with TB or with my configuring it, see above why)?
 
 
 
#5
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SMTP is the tip off - Check and see if things like "secure" are checked or unchecked as needed. Same with authentication.

You may be real good at configuring but this stuff can slip by. TLS works fine with Gmail so I wouldn't be TOO quick to to blame The Bat in this case :-)

Mr. Zharinov
Quote
and well it seemes that your beleif is wrong as even in TB SSL and TLS are different types of protocols for POP3 (you can easily see it when configuring the account).

Where is SSL? I have "regular" "TLS" and "STARTTLS"
Thanks
Rick
 
 
 
#6
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What version of TB are you using? (Mine doesn't offer SSL for POP3 or SMTP, only regular (unsecure), StartTLS and TLS)
Are you using anything like a proxy for outgoing mail?
Are the error messages of TB preceded with 'Server reports:'?
There are lots of people using The Bat! and Gmail and that requires a proper functioning of SMTP over TLS, so it's supposed to work.
Did you try to install TB again? (Something could have gone corrupt.)
What response do you get when you try a regular SMTP connection to port 25?
__________________________________
I'm just a user of The Bat! I don't work for Ritlabs.
 
 
 
#7
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pfff... strange that i don't see it either in 3.85... i remember seeing it in 3.65, which i had just recently replaced by 3.85. well but anyway, i might be wrong =).

i don't use any proxy. regular SMTP is closed long ago, but i will try tomorrow, it's a good point to seeing the difference. reinstalling is also a good point.

the messages are as is, i just copied them from the log.

what can the message "TLS protocol error" mean i wander?
 
 
 
#8
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I checked 3.65.4 (a beta) that didn't have SSL available.

Don't bother checking a regular connection, I just checked the results when you're running TLS and StartTLS against a port that only supports regular, that gives something like:
5-10-2006, 00:01:00: SEND  - Initiating TLS handshake
5-10-2006, 00:01:00: SEND  - connection finished - 0 messages sent
or (with StartTLS):
!5-10-2006, 00:00:04: SEND  - Server reports error. The response is: unknown command, expected MAIL
!5-10-2006, 00:00:04: SEND  - Server reports it is not ready, reply: "unknown command, expected MAIL"

So we should look somewhere else.  
__________________________________
I'm just a user of The Bat! I don't work for Ritlabs.
 
 
 
#9
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http://www.ietf.org/rfc/rfc2246.txt

Code
3. Goals of this document 
   This document and the TLS protocol itself are based on the SSL 3.0 Protocol Specification as published by Netscape. The differences between this protocol and SSL 3.0 are not dramatic, but they are significant enough that TLS 1.0 and SSL 3.0 do not interoperate  (although TLS 1.0 does incorporate a mechanism by which a TLS implementation can back down to SSL 3.0). This document is intended primarily for readers who will be implementing the protocol and those doing cryptographic analysis of it. The specification has been written with this in mind, and it is intended to reflect the needs of those two groups. For that reason, many of the algorithm-dependent data structures and rules are included in the body of the text (as opposed to in an appendix), providing easier access to them.  
   This document is not intended to supply any details of service definition nor interface definition, although it does cover select areas of policy as they are required for the maintenance of solid security.
 
 
 
#10
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blah... i've turned off "Require secure auth" in "Authentication" settings for SMTP and it started to work. can someone explain me what does that "secure auth" means?
 
 
 
#11
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In order to authenticate yourself with the SMTP server you need to exchange user name and password.
When you're doing that over an unsecure connection you can choose to encrypt your user name and password (using MD5), that's what's meant with 'secure authentication'.
However you're using a secure connection, so it has no real value to encrypt your credentials
__________________________________
I'm just a user of The Bat! I don't work for Ritlabs.
 
 
 
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