javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 25;

by

Sounds like a firewall problem (firewalls silently drop packets that are not allowed, which is why you would be seeing a Connection Timeout.

Can you try

H:\> telnet smtp.gmail.com 25
Connecting To smtp.gmail.com...Could not open connection to the host, on port 25
: Connect failed

on your server and see whether you get a connection? (I’m behind a firewall here that does not allow connections to gmail)

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