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in reply to Re^3: 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

Well then, the mystery deepens.

Executing:

telnet smtp.gmail.com 25

produces the following output:

220 mx.google.com ESMTP l71sm1167256yhj.15

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Re^5: MIME::Lite error => SMTP auth() command not supported on smtp.gmail.com
by keszler (Priest) on Sep 14, 2011 at 23:27 UTC

    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.)

      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.

      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

        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.