Think of it this way: You have two versions of dosomething.exe installed; One lists files, and one prints hello world. You put the lists-files one in your path so that you can type "dosomething" and a file listing occurs. To get to the hello-world version, you have to use its fully-qualified name; the absolute path, because there are two different executables on your system by the same name. If you were to update your path to find the hello-world version of dosomething.exe first, it would win when you type the command name, and you would then have to type the full path to reach the list-files version of dosomething.exe

You have two executables on your system that both are named perl.exe. One of them is a 2002 version of Active State Perl. One is a newer version of Strawberry Perl. They reside at different places on your filesystem, and their libraries live at different places. They usually can co-exist but it's possible the old ActiveState install is broken. But your question really relates to how to make Strawberry Perl's perl.exe get priority in your PATH. That would be the same question whether we're talking about perl.exe or dosomething.exe.

Both Strawberry and ActiveState behave pretty well according to Win32 path and install standards. Whether the previous admin of this box kept to those standards, might be another story. Managing environment variables on Windows Server 2012 is more of a Windows Server admin question than a Perl question. That being said, it's pretty easy: Control Panel > System and Security > System > Advanced System Settings, and then look for the Environment Variables button (might be in a different tab), or ask your network admin for assistance.