Re^5: MIME::Lite error => SMTP auth() command not supported on smtp.gmail.com

[keszler]

in reply to Re^4: MIME::Lite error => SMTP auth() command not supported on smtp.gmail.com
in thread MIME::Lite error => SMTP auth() command not supported on smtp.gmail.com

Odd. How did you check that MIME::Base64 and Authen::SASL were working? Try:

DOS> perl -e "require MIME::Base64;"
DOS> perl -e "require Authen::SASL;"

Any error messages?

If not, all I can guess is that copying Perl + modules != installing Perl + modules. I'd suggest renaming the server's Perl64 directory, then doing a full install of Perl and the modules you use. (Run C:\Perl64\bin\instmodsh.bat on your workstation to generate a list of installed modules.)

[ted.byers]

Here is the content of the session I started to test this:

C:\>perl -v

This is perl 5, version 12, subversion 1 (v5.12.1) built for MSWin32-x
+64-multi-thread
(with 3 registered patches, see perl -V for more detail)

Copyright 1987-2010, Larry Wall

Binary build 1201 [292674] provided by ActiveState http://www.ActiveSt
+ate.com
Built May 14 2010 00:22:26

Perl may be copied only under the terms of either the Artistic License
+ or the
GNU General Public License, which may be found in the Perl 5 source ki
+t.

Complete documentation for Perl, including FAQ lists, should be found 
+on
this system using "man perl" or "perldoc perl".  If you have access to
+ the
Internet, point your browser at http://www.perl.org/, the Perl Home Pa
+ge.


C:\>perl -e "require MIME::Base64;"

C:\>perl -e "require Authen::SASL;"

C:\>

I'll try to do a regular install, and see (and report back) what happens.

[ted.byers]

Well, I did as you suggested, renamed Perl64 and installed Perl de novo, and installed the requisite packages, and the result remains the same.

I don't know what else to try

[keszler]

The next step I'd recommend is running Wireshark on each box, capturing packets to and from the gmail server. On the workstation you should get the complete set of connect, auth, send, and quit; comparing that with however far the server gets might provide helpful data (different ports, commands, etc). Once you know what is different you'll be closer to figuring out why.

[ted.byers]

I suspect something is awry with the security required to set up a TLS session. On the two servers where the script fails, I get everything up to where TLS ought to start, but no TLSv1 packets. On the workstation where all works, I get a large number of TLSv1 packets, followed by those SMTP packets that end it all. But, I am having an aweful time trying to get Wireshark to display/export, only those packets relevant to the SMTP session (but that may be due to the fact I have never used Wireshark before). And, there are a lot of packets exchanged between the workstation and server and the router, many of which are related to the SMTP session, and seem to be duplicated between the router's public IP address and the gmail email server. What sorts of things need I investigate to determine why neither server can establish the TLS connection that smtp.gmail.com apparently needs? Thanks Ted