Windows – Problem in installing & configuring bugzilla

For anyone trying to set up Bugzilla's email feature to use Gmail on a windows machine, I just spent two and a half days at work with dawood's solution http://www.dawood.in/bugzilla_alerts_using_gmail.html, to no avail. My machine is running 64 bit Windows 7, And I eventually did find a solution, skip to the third paragraph for that. Here's why Dawood's solution won't work for most windows users:

Chances are, if you installed Bugzilla the by following the (awesome) tutorials, you installed ActivePerl. The Email::Send::SMTP::TLS perl package that Dawood's solution revolves around depends upon an Email::SMTP::TLS::ButMaintained package, which, in turn, depends upon a Net::SSLeay package. (This is why, even after following Dawood's instructions and modifying Mailer.pm, no "SMTP::TLS" option appears in the drop down list. The dependencies aren't resolved.) The trouble is, Net::SSLeay will only install if it is compiled with THE SAME compiler you used to compile Perl. In addition, The documentation says: "Please do not even dream of copying a perl binary or installing perl binary from a package." Oh... whoops... ActivePerl is binary installed from a package. Since that won't work, here's what will.

To configure Bugzilla to send mail through Gmail's smtp server:

1. Download Glob's sendmail wrapper for windows at http://glob.com.au/sendmail/, and unzip
2. copy sendmail.exe and sendmail.ini to \usr\lib on the drive where the unix application is installed. So if Bugzilla is installed at C:\Bugzilla, create a 'usr' folder at the root level of the C: drive, with a 'lib' folder within that.
3. open up sendmail.ini.
4. within sendmail.ini copy and paste these values on the appropriate lines:
   • smtp_server=smtp.gmail.com:587
   • smtp_ssl=tls
   • auth_username=<INSERT YOUR USERNAME HERE>
   • auth_password=<INSERT YOUR PASSWORD HERE>
   • if your gmail server runs on a specific domain, make sure to uncomment and fill in the default_domain parameter.
5. now go to the Administration tab in Bugzilla, and select Parameters
6. Choose Email from the sidebar on the left.
7. In the pulldown menu under mail_delivery_method, select Sendmail.
8. You're done! Bugzilla will send email through gmail's smtp server.

A shot in the dark, but something I've seen before -- have you made sure that the file share it's coming from allows "Domain Computers" Read and Execute permissions?

To test, run PsExec -s cmd.exe, which will give you a command prompt running as System. From there try to run the MSI and see if you can.