214660 - Cannot send mail using SMTP/SSL (smtps) and username/password authentication

Status: RESOLVED DUPLICATE of bug 135357

(MailNews Core :: Networking: SMTP, defect)

Description

[RT]

User-Agent:       Mozilla/5.0 (Macintosh; U; PPC Mac OS X Mach-O; en-US; rv:1.4) Gecko/20030624
Build Identifier: Mozilla/5.0 (Macintosh; U; PPC Mac OS X Mach-O; en-US; rv:1.4) Gecko/20030624

In addition to the above, I am using a 800MHz Powerbook with 512M RAM. 

My ISP uses SMTP with SSL for sending email (port 465), and uses
username/password for user authentication.

I am unable to send mail using this ISP.  Receiving mail using IMAP/SSL and
username/password authentication works fine.

In using ethereal to sniff the SMTP/SSL transactions I find a TCP SYN going to
the server, a SYN ACK coming back, and then Mozilla Mail/News sends a ACK, and
then all transactions stop dead.

During this time the "Sending Mail" progress dialog is up and spinning.

Reproducible: Always

Steps to Reproduce:
1. Set up Mail to use SMTP / SSL on a Mac OS X platform, Mozilla 1.4
2. Try sending mail.

Comment 1

[Matthias Versen [:Matti]]

Can you create a SMTP log and attach it to this bug ?
http://www.mozilla.org/quality/mailnews/mail-troubleshoot.html

Comment 2

[RT]

Attachment: prefs.js file

Comment 3

[RT]

I created a log file, as requested.  The only thing which appears is:

-1610609172[290340]: SMTP Connecting to: imailhost.worldnet.att.net

That's ALL there is in the entire log file, one per send attempt.

For laughs I created another dummy SMTP account which used username and
password, and the system prompts me for it when I try to send, even if the
mailserver doesn't use SMTP (I used an Microsoft Exchange Server to test
against).  However it never prompts me when I use port 465 against AT&T
Worldnet's SMTP server, I just get the "Sending mail..." progress window forever.

I've attached my prefs.js file for laughs if you need it.  To be clear, the
options in the "Mail and Newsgroup Account Settings" for "Outgoing Server
(SMTP)" are: SSL = always, "Use name and password" is checked, and port is 465.

Here are the combinations I have tried:

1. SMTP port is blank: no matter what the SSL setting is (Always/Try/Never), no
response from SMTP server because Mozilla keeps trying port 25 (shouldn't SMTP
be using the SMTPS port 465 when SSL is set to "Always"?)

2. SMTP port is 465: no matter what the SSL setting is, I see the SYN, SYN ACK,
ACK sequence from Mozilla to the SMTP server, and then nothing.

3. All manners of "Use name and password" settings: same symptoms as (2).

Comment 4

[Christian Eyrich]

Huh, I had to do some searches to get a thought what's going on.
The server wants to use SMTP over SSL, but Mozilla doesn't know this form of
communication at the moment.

When activating SSL (better would be to say TLS but I guess it's called SSL
because most users don't know TLS) in SMTP, Mozilla want's to use the STARTTLS
extension in means of RFC 2487.

SMTPS connects to the server using a SSL link and then starts SMTP communication.
Mozilla awaits to start a normal (E)SMTP connection and then chooses TLS.

So the server and Mozilla don't understand each other.

*** This bug has been marked as a duplicate of 135357 ***