(Ruby) Send Email with Multiple Reply-To Addresses

Send email with multiple repy-to addresses.

Note: Some mail servers will remove the extra email addresses from the Reply-To header. Even if you provide multiple reply-to addresses, the email may arrive with only the 1st.

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.

mailman = Chilkat::CkMailMan.new()

mailman.put_SmtpHost("smtp.my_mail_server.com")
mailman.put_SmtpUsername("myUsername")
mailman.put_SmtpPassword("myPassword")
mailman.put_SmtpPort(465)
mailman.put_SmtpSsl(true)

# 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("Joe <joe@example.com>")
success = email.AddTo("Mary","mary@example2.com")

# Specify a single reply-to address, which will get replace with a list of addresses..
email.put_ReplyTo("placeholder@example.com")

# Get the email as MIME.
sbMime = Chilkat::CkStringBuilder.new()
mailman.RenderToMimeSb(email,sbMime)

# Update the Reply-To MIME header with a list of email addresses.
replyToAddrs = "joe@example.com, mike@example.com"
sbMime.ReplaceAllBetween("Reply-To: ","\r\n",replyToAddrs,false)

# Examine the MIME to be sent:
print sbMime.getAsString() + "\n";

# Here's the MIME:

# MIME-Version: 1.0
# Date: Tue, 03 Sep 2024 08:18:12 -0500
# Message-ID: <D892B0E563A7A13B1F499530DE21529714EA479A@SLICE>
# Content-Type: text/plain; charset=us-ascii; format=flowed
# Content-Transfer-Encoding: 7bit
# X-Priority: 3 (Normal)
# Subject: This is a test
# From: Joe <joe@example.com>
# To: Mary <mary@example2.com>
# Reply-To: joe@example.com, mike@example.com
# 
# This is a test

# ---------
# Send the MIME...
success = mailman.SendMime("joe@example.com","mary@example2.com",sbMime.getAsString())
if (success == false)
    print mailman.lastErrorText() + "\n";
    exit
end

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

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