It sounds like you want to insert the breakpoint at the if ($cmd =~ /INITIAL/i) line. Let's say that's line 123. Then, type:
b 123 $cmd =~ /INITIAL/i
Setting it to the subroutine entry is problematic because $cmd isn't set yet (or at least isn't set to a member of @commands. In addition to that, simply using /INITIAL/i as your condition would be running that regexp on $_, not $cmd.
See perldebug for more info.
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