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IO::Socket::SSL requires CA bundle location to be defined
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IO::Socket::SSL requires CA bundle location to be defined
Still using this script in 2020! 👍
NOTE: I'm not an expert just needed this to work and found a way!
Tested with Gmail TLS on port 587
[13:29 srvXXXXX ~]# /usr/bin/sendemail -t to@gmail.com -f from@gmail.com -u TESTSUBJECT -m TESTMESSAGE -s smtp.gmail.com:587 -xu from@gmail.com -xp password -v -v -o tls=yes
Aug 02 13:29:54 srvXXXXX sendemail[13611]: DEBUG => Connecting to smtp.gmail.com:587
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => My IP address is: 192.168.X.XX
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => evalSMTPresponse() - Found SMTP success code: 220
Aug 02 13:29:55 srvXXXXX sendemail[13611]: SUCCESS => Received: 220 smtp.gmail.com ESMTP n11sm12221358wmi.15 - gsmtp
Aug 02 13:29:55 srvXXXXX sendemail[13611]: INFO => Sending: EHLO srvXXXXX
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => evalSMTPresponse() - Found SMTP success code: 250
Aug 02 13:29:55 srvXXXXX sendemail[13611]: SUCCESS => Received: 250-smtp.gmail.com at your service, [85.244.XX.XX], 250-SIZE 35882577, 250-8BITMIME, 250-STARTTLS, 250-ENHANCEDSTATUSCODES, 250-PIPELINING, 250-CHUNKING, 250 SMTPUTF8
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => The remote SMTP server supports TLS :)
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => Starting TLS
Aug 02 13:29:55 srvXXXXX sendemail[13611]: INFO => Sending: STARTTLS
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => evalSMTPresponse() - Found SMTP success code: 220
Aug 02 13:29:55 srvXXXXX sendemail[13611]: SUCCESS => Received: 220 2.0.0 Ready to start TLS
Using the default of SSL_verify_mode of SSL_VERIFY_NONE for client
is deprecated! Please set SSL_verify_mode to SSL_VERIFY_PEER
possibly with SSL_ca_file|SSL_ca_path for verification.
If you really don't want to verify the certificate and keep the
connection open to Man-In-The-Middle attacks please set
SSL_verify_mode explicitly to SSL_VERIFY_NONE in your application.
at /usr/bin/sendemail line 1908.
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => TLS session initialized :)
Aug 02 13:29:55 srvXXXXX sendemail[13611]: INFO => Sending: EHLO srvXXXXX
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => evalSMTPresponse() - Found SMTP success code: 250
Aug 02 13:29:55 srvXXXXX sendemail[13611]: SUCCESS => Received: 250-smtp.gmail.com at your service, [85.244.XX.XX], 250-SIZE 35882577, 250-8BITMIME, 250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH, 250-ENHANCEDSTATUSCODES, 250-PIPELINING, 250-CHUNKING, 250 SMTPUTF8
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => SMTP-AUTH: Using LOGIN authentication method
Aug 02 13:29:55 srvXXXXX sendemail[13611]: INFO => Sending: AUTH LOGIN
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => evalSMTPresponse() - Found SMTP success code: 334
Aug 02 13:29:55 srvXXXXX sendemail[13611]: SUCCESS => Received: 334 VXNlcm5hbWU6
Aug 02 13:29:55 srvXXXXX sendemail[13611]: INFO => Sending: cmVkb3drQGdtYWlsLmNvbQ==
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => evalSMTPresponse() - Found SMTP success code: 334
Aug 02 13:29:55 srvXXXXX sendemail[13611]: SUCCESS => Received: 334 UGFzc3dvcmQ6
Aug 02 13:29:55 srvXXXXX sendemail[13611]: INFO => Sending: eWJweHh0cGN2cHBwYXdrbg==
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => evalSMTPresponse() - Found SMTP success code: 235
Aug 02 13:29:55 srvXXXXX sendemail[13611]: SUCCESS => Received: 235 2.7.0 Accepted
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => User authentication was successful (Method: LOGIN)
Aug 02 13:29:55 srvXXXXX sendemail[13611]: INFO => Sending: MAIL FROM:from@gmail.com
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => evalSMTPresponse() - Found SMTP success code: 250
Aug 02 13:29:55 srvXXXXX sendemail[13611]: SUCCESS => Received: 250 2.1.0 OK n11sm12221358wmi.15 - gsmtp
Aug 02 13:29:55 srvXXXXX sendemail[13611]: INFO => Sending: RCPT TO:to@gmail.com
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => evalSMTPresponse() - Found SMTP success code: 250
Aug 02 13:29:55 srvXXXXX sendemail[13611]: SUCCESS => Received: 250 2.1.5 OK n11sm12221358wmi.15 - gsmtp
Aug 02 13:29:55 srvXXXXX sendemail[13611]: INFO => Sending: DATA
Aug 02 13:29:55 srvXXXXX sendemail[13611]: DEBUG => evalSMTPresponse() - Found SMTP success code: 354
Aug 02 13:29:55 srvXXXXX sendemail[13611]: SUCCESS => Received: 354 Go ahead n11sm12221358wmi.15 - gsmtp
Aug 02 13:29:55 srvXXXXX sendemail[13611]: INFO => Sending message body
Aug 02 13:29:55 srvXXXXX sendemail[13611]: Setting content-type: text/plain
Aug 02 13:29:56 srvXXXXX sendemail[13611]: DEBUG => evalSMTPresponse() - Found SMTP success code: 250
Aug 02 13:29:56 srvXXXXX sendemail[13611]: SUCCESS => Received: 250 2.0.0 OK 1596371397 n11sm12221358wmi.15 - gsmtp
Aug 02 13:29:56 srvXXXXX sendemail[13611]: Email was sent successfully! From: from@gmail.com To: to@gmail.com Subject: [TESTSUBJECT] Server: [smtp.gmail.com:587]
[13:29 srvXXXXX ~]#