silent failure when creating new Net::SMTP::SSL object - perl

Question

[Running perl 5.16.2 on OS X 10.9.5]
I have a little Secret Santa perl script I dust off once a year, and now this time it has decided to give me a hassle. (I do have a new computer as well, so there does exist a different environment from last year.) I am calling:
$smtp = Net::SMTP::SSL->new(Host => "mail.mydomain.org", Port => 465);
and when this returns, $smtp contains no value ('p $smtp' in the perl debugger just displays a blank line) and subsequent accesses like $stmp->domain (and $smtp->auth()) fail with the error
Can't call method "domain" on an undefined value at ./secretsanta.pl line 67.
What am I missing here? Thanks for any pointers.
EDIT: when I turn on SSL debugging (perl -MIO::Socket::SSL=debug4 secretsanta.pl) I get:
DEBUG: .../IO/Socket/SSL.pm:1769: Invalid default certificate authority locations
SSL error: 8606: 1 - error:2006D002:BIO routines:BIO_new_file:system lib
SSL error: 8606: 2 - error:0B084002:x509 certificate routines:X509_load_cert_crl_file:system lib
DEBUG: .../IO/Socket/SSL.pm:1774: Invalid default certificate authority locations error:0200100D:system library:fopen:Permission denied
DEBUG: .../IO/Socket/SSL.pm:529: socket not yet connected
DEBUG: .../IO/Socket/SSL.pm:531: socket connected
DEBUG: .../IO/Socket/SSL.pm:553: ssl handshake not started
DEBUG: .../IO/Socket/SSL.pm:1769: SSL structure creation failed
DEBUG: .../IO/Socket/SSL.pm:1774: SSL structure creation failed error:140BA0C3:SSL routines:SSL_new:null ssl ctx
DEBUG: .../IO/Socket/SSL.pm:1758: IO::Socket::INET configuration failed
(I am using an SSL cert provided by my hosting company that doesn't match the DNS name of my mail server, but obviously something changed from last year to cause this not to work.)

Answer 1

Have you checked whether, by upgrading, you are affected by one of those bugs (first perhaps):
Cpan Bug reports
Seems to me that fits: new computer -> perhaps updated versions ->
bug with SMTP 2.35+ ( first in list ).
Perhaps you should simply use Net::SMTP itself?

Answer 2

I tried a few things. I installed Perl 5.18.2 (x86) for Windows and got past the empty SMTP-SSL connector, but was having problems resolving a '554 5.7.1 client host rejected' error. I ended up going back to the Mac, changing my password temporarily and using the insecure Net::SMTP to send the email, then changing password again. Obviously some bug, but I just needed this to be done with.

Answer 3

IO::Socket::SSL: 2.002
Which is the newest version. If you run your script only once a year there changed a lot in the mean time.
DEBUG: .../IO/Socket/SSL.pm:1769: Invalid default certificate authority locations
SSL error: 8606: 1 - error:2006D002:BIO routines:BIO_new_file:system lib
SSL error: 8606: 2 - error:0B084002:x509 certificate routines:X509_load_cert_crl_file:system lib
Looks like it found a CA path, but has some problems to use it. Could you please check what it found, that is
perl -MIO::Socket::SSL -MData::Dumper -e 'warn Dumper({ IO::Socket::SSL::default_ca() })'
If this returns a SSL_ca_path setting with a directory as value make sure that all files in this directory are actually readable by the program.
(I am using an SSL cert provided by my hosting company that doesn't match the DNS name of my mail server, but obviously something changed from last year to cause this not to work.)
This will definitely give problems too, but only once the first problem got fixed. One of the changes in the last year was to enforce some kind of hostname checking by default, because modules using IO::Socket::SSL often forgot to set the proper verification schema for hostnames (Net::SMTP::SSL included).
If this hostname in the certificate differs from what you specify as the destination you need to explicitly use the SSL_verifycn_name setting to define the expected hostname.
BTW, since about a month libnet (which provides the CORE modules Net::SMTP, Net::FTP, ...) has support for SSL/TLS if IO::Socket::SSL is installed. This includes support for direct SSL and STARTTLS, so you don't need any special case modules like Net::SMTP::SSL (only direct SSL), Net::SMTP::TLS (only STARTTLS) or Net::SSLGlue::SMTP (monkey patches Net::SMTP to support both) any longer.