Re: Problem sending Gmail from Widows 10

global error: SSL Version SSLv2 not supported
[download]

Most likely, your version of IO::Socket::SSL does not support SSLv2. This should be OK according to IO::Socket::SSL because SSLv2 and SSLv3 have serious security issues and should not be used anymore.

Maybe you can pass the appropriate SSL_version configuration to Email::Send::SMTP::Gmail or set it somewhere where IO::Socket::SSL can pick it up? I'm not really sure why Google would only want to talk SSLv2 with you(r program), so maybe you can investigate why such an insecure encryption layer would be used...

Comment on Re: Problem sending Gmail from Widows 10 Select or Download Code

Replies are listed 'Best First'.
Re^2: Problem sending Gmail from Widows 10 by haprst (Initiate) on Nov 14, 2015 at 16:40 UTC
Unfortunately, the advice of all three people didn't help. Curiously, if I change the case from -layer=> 'tls', to -layer=> 'TLS', then the error messages change entirely: ... Net::SMTPS=GLOB(...etc...)>>>> EHLO localhost.localdomain Net::SMTPS=GLOB(...etc...)>>>> 250-smtp.gmail.com at your service .. +. Net::SMTPS=GLOB(...etc...)>>>> 250-SIZE 35882577 Net::SMTPS=GLOB(...etc...)>>>> 250-8BITMIME Net::SMTPS=GLOB(...etc...)>>>> 250-STARTTLS Net::SMTPS=GLOB(...etc...)>>>> 250-ENHANCEDSTATUSCODES Net::SMTPS=GLOB(...etc...)>>>> 250-PIPELINING Net::SMTPS=GLOB(...etc...)>>>> 250-CHUNKING Net::SMTPS=GLOB(...etc...)>>>> 250 SMTPUTF8 Net::SMTPS=GLOB(...etc...)>>>> AUTH LOGIN Net::SMTPS=GLOB(...etc...)>>>> 530 5.7.0 Must issue a STARTTLS comma +nd first ... Authentication (SMTP) failed [download] but note that one of the messages confirmed STARTTLS already.	[reply] [d/l]
Re^3: Problem sending Gmail from Widows 10 by afoken (Chancellor) on Nov 14, 2015 at 18:29 UTC
Net::SMTPS=GLOB(...etc...)>>>> EHLO localhost.localdomain Net::SMTPS=GLOB(...etc...)>>>> 250-smtp.gmail.com at your service .. +. Net::SMTPS=GLOB(...etc...)>>>> 250-SIZE 35882577 Net::SMTPS=GLOB(...etc...)>>>> 250-8BITMIME Net::SMTPS=GLOB(...etc...)>>>> 250-STARTTLS Net::SMTPS=GLOB(...etc...)>>>> 250-ENHANCEDSTATUSCODES Net::SMTPS=GLOB(...etc...)>>>> 250-PIPELINING Net::SMTPS=GLOB(...etc...)>>>> 250-CHUNKING Net::SMTPS=GLOB(...etc...)>>>> 250 SMTPUTF8 Net::SMTPS=GLOB(...etc...)>>>> AUTH LOGIN Net::SMTPS=GLOB(...etc...)>>>> 530 5.7.0 Must issue a STARTTLS comma +nd first ... Authentication (SMTP) failed [download] but note that one of the messages confirmed STARTTLS already. Are you sure? I only see an SMTP server identifying as smtp.gmail.com announcing its capabilities conforming to RFC1869, which are 8 bit MIME messages, TLS encrypted communication, enhanced status codes, and so on. I don't see any TLS confirmation here. RFC2487 documents that the `EHLO` command needs to be followed by a `STARTTLS` command. Your output shows `AUTH LOGIN` instead. Alexander -- Today I will gladly share my knowledge and experience, for there are no sweeter words than "I told you so". ;-)	[reply] [d/l] [select]