I believe i had the same issue with SSL and after installing Mozilla::CA it still did not work until i forced the reinstall of LWP::UserAgent
I did a force reinstall with sudo cpan -f -i LWP::UserAgent and for Mozilla::CA seemed to reinstall it. However I get the same error.
rcork, are you using OSX perl 5.12 or a newer version? If so, how did you upgrade?
EDIT: I also tried getting twitter to work, I get the following error, maybe this will give a clue regarding my prowl perl problems.
installed twitter, made dev and get this error.
CPAN: Storable loaded ok (v2.22)
Reading '/Users/myun/.cpan/Metadata'
Database was generated on Wed, 14 Aug 2013 23:53:03 GMT
CPAN: Module::CoreList loaded ok (v2.50)
Net::Twitter::Lite::WithAPIv1_1 is up to date (0.12004).
$ sudo cpan install Net::OAuth
CPAN: Storable loaded ok (v2.22)
Reading '/Users/myun/.cpan/Metadata'
Database was generated on Wed, 14 Aug 2013 23:53:03 GMT
CPAN: Module::CoreList loaded ok (v2.50)
Net::OAuth is up to date (0.28).
plexWatch$ ./plexWatch.pl --test_notify=start
Can't locate Net/Twitter/Lite/WithAPIv1_1.pm in @INC (@INC contains: /Library/Perl/5.12/darwin-thread-multi-2level /Library/Perl/5.12 /Network/Library/Perl/5.12/darwin-thread-multi-2level /Network/Library/Perl/5.12 /Library/Perl/Updates/5.12.4/darwin-thread-multi-2level /Library/Perl/Updates/5.12.4 /System/Library/Perl/5.12/darwin-thread-multi-2level /System/Library/Perl/5.12 /System/Library/Perl/Extras/5.12/darwin-thread-multi-2level /System/Library/Perl/Extras/5.12 .) at ./plexWatch.pl line 45
UPDATE
installed plexWatch on my personal mac, fresh from dev tools like homebrew and port, everything worked fine including push. I'll try to figure out a way to clean my server's setup, I'll update if it's resolved.
ljunkie and rcork, thank you for the support.
UPDATE2
removed homebrew and macports... force reinstalled modules, highly recommend installing Mozilla::CA prior to LWP::UserAgent
everything seems to be working!