in reply to Problem sending Gmail from Widows 10
Regarding the messages.
DEBUG: .../IO/Socket/SSL.pm:525 refers to the 525th line of the installed SSL.pm module, as the place of message origin.
250-STARTTLS in the EHLO response indicates the availability (server willingness). Line with 530 is the actual error.
Email::Send::SMTP::Gmail has Net::SSLeay among its dependencies. Net::SSLeay provides the actual glue to openssl library.
See if you can increase the debugging level by including
$Net::SSLeay::trace = 2;in your program. The detailed handshake may bring you closer to the cause of the failure.
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