Description: ------------ I am attempting to create a secure connection to an Exchange 2003 server, using TLS. The Exchange server supports NTLM and LOGIN Authentication, but will only allow LOGIN authentication over a TLS connection. It appears that the Net_SMTP will only allow a TLS connection if there are no AUTH methods available, and hence the connection fails. Actual result: -------------- DEBUG: Recv: 220 exc01.x.net Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 3 Nov 2008 14:35:25 +0000 DEBUG: Send: EHLO localhost DEBUG: Recv: 250-exc01.x.net Hello [10.0.0.252] DEBUG: Recv: 250-TURN DEBUG: Recv: 250-SIZE DEBUG: Recv: 250-ETRN DEBUG: Recv: 250-PIPELINING DEBUG: Recv: 250-DSN DEBUG: Recv: 250-ENHANCEDSTATUSCODES DEBUG: Recv: 250-8bitmime DEBUG: Recv: 250-BINARYMIME DEBUG: Recv: 250-CHUNKING DEBUG: Recv: 250-VRFY DEBUG: Recv: 250-TLS DEBUG: Recv: 250-STARTTLS DEBUG: Recv: 250-X-EXPS GSSAPI NTLM LOGIN DEBUG: Recv: 250-X-EXPS=LOGIN DEBUG: Recv: 250-AUTH GSSAPI NTLM LOGIN DEBUG: Recv: 250-AUTH=LOGIN DEBUG: Recv: 250-X-LINK2STATE DEBUG: Recv: 250-XEXCH50 DEBUG: Recv: 250 OK DEBUG: Send: AUTH LOGIN DEBUG: Recv: 530 5.7.0 Must issue a STARTTLS command first DEBUG: Send: RSET DEBUG: Recv: 530 5.7.0 Must issue a STARTTLS command first DEBUG: Send: QUIT DEBUG: Recv: 221 2.0.0 exc01.x.net Service closing transmission channel

Sorry, forgot to add, the file where the error is is "Net/SMTP.php", line number is 461.

It looks like Chuck added the STARTTLS code original and explicitly put it within that conditional. I don't know the standard well enough to know the reasoning there, though.

I got the same problem when trying to send e-mails from my scripts using smtp authentication. And to fix it I had to correct line 463 on SMTP.php to look like this. if (!empty($this->_esmtp['AUTH'])) { it seems that if the mail server answer within the _negotiate() call over a non secure query that it uses authentication, the client trying to authenticate will not use TLS, hence the server will refuse authentication. Perhaps instead of asking if _esmtp['AUTH'] is empty, it would be more precise to ask if _esmtp['TLS'] or if _esmtp['STARTTLS']is set. By following the process of sending mail, the _negotiate() fucntion is called before it tryes to authenticate, and that's why _esmtp['AUTH'] gets populated, so is never empty by the time it gets to the auth() function. Hope this helps In my case I had to download the latest version of sockets.php as well. and everythning worked fine.

Please be aware that my fix is ONLY a fast fix. It is just meant to force the process to start the TLS channel under my particular circumstances. From my gathering, the auth() function has to be reshaped a little in order to account for all possible scenarios

Thank you for your bug report. This issue has been fixed in the latest released version of the package, which you can download at http://pear.php.net/get/Net_SMTP