(Ruby) Office365 Send Email using SMTP with OAuth2 Authentication

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Chilkat Ruby Downloads install from rubygems.org gem install chilkat or download... Ruby Library for Windows, MacOS, Linux, Alpine Linux

require 'chilkat'

# This example requires the Chilkat API to have been previously unlocked.
# See Global Unlock Sample for sample code.

# An Office365 OAuth2 access token must first be obtained prior
# to running this code.

# Getting the OAuth2 access token for the 1st time requires the O365 account owner's 
# interactive authorization via a web browser.  Afterwards, the access token
# can be repeatedly refreshed automatically (with no user interaction).

# See the following examples for getting and refreshing an OAuth2 access token

# Get Office365 SMTP/IMAP/POP3 OAuth2 Access Token
# Refresh Office365 SMTP/IMAP/POP3 OAuth2 Access Token

# First get our previously obtained OAuth2 access token.
jsonToken = Chilkat::CkJsonObject.new()
success = jsonToken.LoadFile("qa_data/tokens/office365.json")

mailman = Chilkat::CkMailMan.new()

mailman.put_SmtpHost("smtp.office365.com")
mailman.put_SmtpPort(587)
mailman.put_StartTLS(true)

# Use your Office365 email address for the SmtpUsername.
mailman.put_SmtpUsername("OFFICE365_EMAIL_ADDRESS")
mailman.put_OAuth2AccessToken(jsonToken.stringOf("access_token"))

# Create a new email object
email = Chilkat::CkEmail.new()

email.put_Subject("This is a test")
email.put_Body("This is a test")
email.put_From("MY_NAME <OFFICE365_EMAIL_ADDRESS>")
success = email.AddTo("John Doe","somebody@example.com")

# Call SendEmail to connect to the SMTP server and send.
# The connection (i.e. session) to the SMTP server remains
# open so that subsequent SendEmail calls may use the
# same connection.  
success = mailman.SendEmail(email)
if (success != true)
    print mailman.lastErrorText() + "\n";
    exit
end

# If SendEmail failed because of "Failed to get initial SMTP Response", then it may be 
# a firewall or anti-virus blocking communications.
# See https://cknotes.com/smtp-office365-com-failed-to-get-initial-smtp-response/

success = mailman.CloseSmtpConnection()
if (success != true)
    print "Connection to SMTP server not closed cleanly." + "\n";
end

print "Mail Sent!" + "\n";