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Merge pull request #1577 from mikel/backport-1536
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Backport 1536
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@eval
eval authored Jan 3, 2024
2 parents 5632473 + 3f05820 commit ef51505
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119 changes: 77 additions & 42 deletions lib/mail/network/delivery_methods/smtp.rb
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Original file line number Diff line number Diff line change
Expand Up @@ -3,40 +3,48 @@

module Mail
# == Sending Email with SMTP
#
#
# Mail allows you to send emails using SMTP. This is done by wrapping Net::SMTP in
# an easy to use manner.
#
#
# === Sending via SMTP server on Localhost
#
#
# Sending locally (to a postfix or sendmail server running on localhost) requires
# no special setup. Just to Mail.deliver &block or message.deliver! and it will
# be sent in this method.
#
#
# === Sending via MobileMe
#
#
# Mail.defaults do
# delivery_method :smtp, { :address => "smtp.me.com",
# :port => 587,
# :domain => 'your.host.name',
# :user_name => '<username>',
# :password => '<password>',
# :authentication => 'plain',
# :enable_starttls_auto => true }
# :enable_starttls => :auto }
# end
#
#
# === Sending via GMail
#
#
# Mail.defaults do
# delivery_method :smtp, { :address => "smtp.gmail.com",
# :port => 587,
# :domain => 'your.host.name',
# :user_name => '<username>',
# :password => '<password>',
# :authentication => 'plain',
# :enable_starttls_auto => true }
# :enable_starttls => :auto }
# end
#
# === Configuring TLS/SSL and STARTTLS
#
# A few remarks:
# - when enabling `tls` (or `ssl`), setting (truthy values for) either `enable_starttls` or `enable_starttls_auto` will raise an ArgumentError as TLS and STARTTLS are mutually exclusive.
# - to configure STARTTLS, use the `enable_starttls`-flag (instead of a combination of `enable_starttls` and `enable_starttls_auto`). Acceptable values are `:always`, `:auto` and `false`.
# - when providing a truthy value for `enable_starttls`, the `enable_starttls_auto`-flag will be ignored.
# - when none of `tls`, `ssl`, `enable_starttls` or `enable_starttls_auto` is set, the fallback will be `enable_starttls` `:auto`.
#
# === Certificate verification
#
# When using TLS, some mail servers provide certificates that are self-signed
Expand All @@ -48,30 +56,30 @@ module Mail
# verify mode constant (OpenSSL::SSL::VERIFY_NONE, OpenSSL::SSL::VERIFY_PEER),
# or a string containing the name of an OpenSSL verify mode (none, peer).
#
# === Others
#
# === Others
#
# Feel free to send me other examples that were tricky
#
#
# === Delivering the email
#
#
# Once you have the settings right, sending the email is done by:
#
#
# Mail.deliver do
# to 'mikel@test.lindsaar.net'
# from 'ada@test.lindsaar.net'
# subject 'testing sendmail'
# body 'testing sendmail'
# end
#
#
# Or by calling deliver on a Mail message
#
#
# mail = Mail.new do
# to 'mikel@test.lindsaar.net'
# from 'ada@test.lindsaar.net'
# subject 'testing sendmail'
# body 'testing sendmail'
# end
#
#
# mail.deliver!
class SMTP
attr_accessor :settings
Expand All @@ -84,7 +92,7 @@ class SMTP
:password => nil,
:authentication => nil,
:enable_starttls => nil,
:enable_starttls_auto => true,
:enable_starttls_auto => nil,
:openssl_verify_mode => nil,
:ssl => nil,
:tls => nil,
Expand All @@ -105,39 +113,66 @@ def deliver!(mail)
end

private
# `k` is said to be provided when `settings` has a non-nil value for `k`.
def setting_provided?(k)
!settings[k].nil?
end

# Yields one of `:always`, `:auto` or `false` based on `enable_starttls` and `enable_starttls_auto` flags.
# Yields `false` when `smtp_tls?`.
# Else defaults to `:auto` when neither `enable_starttls*` flag is provided.
# Providing a truthy value for `enable_starttls` will ignore `enable_starttls_auto`.
def smtp_starttls
return false if smtp_tls?

if setting_provided?(:enable_starttls) && settings[:enable_starttls]
# enable_starttls: provided and truthy
case settings[:enable_starttls]
when :auto then :auto
when :always then :always
else
:always
end
else
# enable_starttls: not provided or false
if setting_provided?(:enable_starttls_auto)
settings[:enable_starttls_auto] ? :auto : false
else
# enable_starttls_auto: not provided
# enable_starttls: when provided then false
# use :auto when neither enable_starttls* provided
setting_provided?(:enable_starttls) ? false : :auto
end
end
end

def smtp_tls?
(setting_provided?(:tls) && settings[:tls]) || (setting_provided?(:ssl) && settings[:ssl])
end

def start_smtp_session(&block)
build_smtp_session.start(settings[:domain], settings[:user_name], settings[:password], settings[:authentication], &block)
end

def build_smtp_session
if smtp_tls? && (settings[:enable_starttls] || settings[:enable_starttls_auto])
raise ArgumentError, ":enable_starttls and :tls are mutually exclusive. Set :tls if you're on an SMTPS connection. Set :enable_starttls if you're on an SMTP connection and using STARTTLS for secure TLS upgrade."
end

Net::SMTP.new(settings[:address], settings[:port]).tap do |smtp|
tls = settings[:tls] || settings[:ssl]
if !tls.nil?
case tls
when true
smtp.enable_tls(ssl_context)
when false
smtp.disable_tls
else
raise ArgumentError, "Unrecognized :tls value #{settings[:tls].inspect}; expected true, false, or nil"
end
elsif settings.include?(:enable_starttls) && !settings[:enable_starttls].nil?
case settings[:enable_starttls]
when true
if smtp_tls?
smtp.disable_starttls
smtp.enable_tls(ssl_context)
else
smtp.disable_tls

case smtp_starttls
when :always
smtp.enable_starttls(ssl_context)
when false
smtp.disable_starttls
else
raise ArgumentError, "Unrecognized :enable_starttls value #{settings[:enable_starttls].inspect}; expected true, false, or nil"
end
elsif settings.include?(:enable_starttls_auto) && !settings[:enable_starttls_auto].nil?
case settings[:enable_starttls_auto]
when true
when :auto
smtp.enable_starttls_auto(ssl_context)
when false
smtp.disable_starttls
else
raise ArgumentError, "Unrecognized :enable_starttls_auto value #{settings[:enable_starttls_auto].inspect}; expected true, false, or nil"
smtp.disable_starttls
end
end

Expand Down
64 changes: 26 additions & 38 deletions spec/mail/network/delivery_methods/smtp_spec.rb
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Original file line number Diff line number Diff line change
Expand Up @@ -2,7 +2,7 @@
# frozen_string_literal: true
require 'spec_helper'

describe "SMTP Delivery Method" do
RSpec.describe "SMTP Delivery Method" do

before(:each) do
MockSMTP.reset
Expand Down Expand Up @@ -202,83 +202,71 @@ def redefine_verify_none(new_value)
to 'ada@test.lindsaar.net'
subject 'Re: No way!'
body 'Yeah sure'
delivery_method :smtp, { :address => "localhost",
:port => 25,
:domain => 'localhost.localdomain',
:user_name => nil,
:password => nil,
:authentication => nil,
:enable_starttls => true }

delivery_method :smtp, { :enable_starttls => true }
end

message.deliver!

expect(MockSMTP.starttls).to eq :always
end

it 'should allow disabling automatic STARTTLS' do
it 'should allow forcing STARTTLS via enable_starttls: :always (overriding :enable_starttls_auto)' do
message = Mail.new do
from 'mikel@test.lindsaar.net'
to 'ada@test.lindsaar.net'
subject 'Re: No way!'
body 'Yeah sure'
delivery_method :smtp, { :address => "localhost",
:port => 25,
:domain => 'localhost.localdomain',
:user_name => nil,
:password => nil,
:authentication => nil,
:enable_starttls => false }

delivery_method :smtp, { :enable_starttls => :always,
:enable_starttls_auto => true }
end

message.deliver!

expect(MockSMTP.starttls).to eq false
expect(MockSMTP.starttls).to eq :always
end

it 'should allow forcing STARTTLS auto' do
it 'should allow detecting STARTTLS via enable_starttls: :auto (overriding :enable_starttls_auto)' do
message = Mail.new do
from 'mikel@test.lindsaar.net'
to 'ada@test.lindsaar.net'
subject 'Re: No way!'
body 'Yeah sure'
delivery_method :smtp, { :address => "localhost",
:port => 25,
:domain => 'localhost.localdomain',
:user_name => nil,
:password => nil,
:authentication => nil,
:enable_starttls_auto => true }

delivery_method :smtp, { :enable_starttls => :auto,
:enable_starttls_auto => false }
end

message.deliver!

expect(MockSMTP.starttls).to eq :auto
end

it 'should allow disabling automatic STARTTLS auto' do
it 'should allow disabling automatic STARTTLS' do
message = Mail.new do
from 'mikel@test.lindsaar.net'
to 'ada@test.lindsaar.net'
subject 'Re: No way!'
body 'Yeah sure'
delivery_method :smtp, { :address => "localhost",
:port => 25,
:domain => 'localhost.localdomain',
:user_name => nil,
:password => nil,
:authentication => nil,
:enable_starttls_auto => false }

delivery_method :smtp, { :enable_starttls => false }
end

message.deliver!

expect(MockSMTP.starttls).to eq false
end

it 'raises when setting STARTTLS with tls' do
message = Mail.new do
from 'mikel@test.lindsaar.net'
to 'ada@test.lindsaar.net'
subject 'Re: No way!'
body 'Yeah sure'
delivery_method :smtp, { :tls => true, :enable_starttls => :always }
end

expect {
message.deliver!
}.to raise_error(ArgumentError, /:enable_starttls and :tls are mutually exclusive/)
end
end

describe "SMTP Envelope" do
Expand Down Expand Up @@ -325,7 +313,7 @@ def redefine_verify_none(new_value)
end.to raise_error(ArgumentError, 'SMTP From address may not be blank: nil')
end

it "should raise an error if no recipient if defined" do
it "should raise an error if no recipient is defined" do
mail = Mail.new do
from "from@somemail.com"
subject "Email with no recipient"
Expand Down

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