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Edit File : smtp.rb \| Size : 30.00 KB
# frozen_string_literal: true # = net/smtp.rb # # Copyright (c) 1999-2007 Yukihiro Matsumoto. # # Copyright (c) 1999-2007 Minero Aoki. # # Written & maintained by Minero Aoki <aamine@loveruby.net>. # # Documented by William Webber and Minero Aoki. # # This program is free software. You can re-distribute and/or # modify this program under the same terms as Ruby itself. # # $Id$ # # See Net::SMTP for documentation. # require 'net/protocol' require 'digest/md5' require 'timeout' begin require 'openssl' rescue LoadError end module Net # Module mixed in to all SMTP error classes module SMTPError # This class is a module for backward compatibility. # In later release, this module becomes a class. end # Represents an SMTP authentication error. class SMTPAuthenticationError < ProtoAuthError include SMTPError end # Represents SMTP error code 4xx, a temporary error. class SMTPServerBusy < ProtoServerError include SMTPError end # Represents an SMTP command syntax error (error code 500) class SMTPSyntaxError < ProtoSyntaxError include SMTPError end # Represents a fatal SMTP error (error code 5xx, except for 500) class SMTPFatalError < ProtoFatalError include SMTPError end # Unexpected reply code returned from server. class SMTPUnknownError < ProtoUnknownError include SMTPError end # Command is not supported on server. class SMTPUnsupportedCommand < ProtocolError include SMTPError end # # == What is This Library? # # This library provides functionality to send internet # mail via SMTP, the Simple Mail Transfer Protocol. For details of # SMTP itself, see [RFC2821] (http://www.ietf.org/rfc/rfc2821.txt). # # == What is This Library NOT? # # This library does NOT provide functions to compose internet mails. # You must create them by yourself. If you want better mail support, # try RubyMail or TMail or search for alternatives in # {RubyGems.org}[https://rubygems.org/] or {The Ruby # Toolbox}[https://www.ruby-toolbox.com/]. # # FYI: the official documentation on internet mail is: [RFC2822] (http://www.ietf.org/rfc/rfc2822.txt). # # == Examples # # === Sending Messages # # You must open a connection to an SMTP server before sending messages. # The first argument is the address of your SMTP server, and the second # argument is the port number. Using SMTP.start with a block is the simplest # way to do this. This way, the SMTP connection is closed automatically # after the block is executed. # # require 'net/smtp' # Net::SMTP.start('your.smtp.server', 25) do \|smtp\| # # Use the SMTP object smtp only in this block. # end # # Replace 'your.smtp.server' with your SMTP server. Normally # your system manager or internet provider supplies a server # for you. # # Then you can send messages. # # msgstr = <<END_OF_MESSAGE # From: Your Name <your@mail.address> # To: Destination Address <someone@example.com> # Subject: test message # Date: Sat, 23 Jun 2001 16:26:43 +0900 # Message-Id: <unique.message.id.string@example.com> # # This is a test message. # END_OF_MESSAGE # # require 'net/smtp' # Net::SMTP.start('your.smtp.server', 25) do \|smtp\| # smtp.send_message msgstr, # 'your@mail.address', # 'his_address@example.com' # end # # === Closing the Session # # You MUST close the SMTP session after sending messages, by calling # the #finish method: # # # using SMTP#finish # smtp = Net::SMTP.start('your.smtp.server', 25) # smtp.send_message msgstr, 'from@address', 'to@address' # smtp.finish # # You can also use the block form of SMTP.start/SMTP#start. This closes # the SMTP session automatically: # # # using block form of SMTP.start # Net::SMTP.start('your.smtp.server', 25) do \|smtp\| # smtp.send_message msgstr, 'from@address', 'to@address' # end # # I strongly recommend this scheme. This form is simpler and more robust. # # === HELO domain # # In almost all situations, you must provide a third argument # to SMTP.start/SMTP#start. This is the domain name which you are on # (the host to send mail from). It is called the "HELO domain". # The SMTP server will judge whether it should send or reject # the SMTP session by inspecting the HELO domain. # # Net::SMTP.start('your.smtp.server', 25, # 'mail.from.domain') { \|smtp\| ... } # # === SMTP Authentication # # The Net::SMTP class supports three authentication schemes; # PLAIN, LOGIN and CRAM MD5. (SMTP Authentication: [RFC2554]) # To use SMTP authentication, pass extra arguments to # SMTP.start/SMTP#start. # # # PLAIN # Net::SMTP.start('your.smtp.server', 25, 'mail.from.domain', # 'Your Account', 'Your Password', :plain) # # LOGIN # Net::SMTP.start('your.smtp.server', 25, 'mail.from.domain', # 'Your Account', 'Your Password', :login) # # # CRAM MD5 # Net::SMTP.start('your.smtp.server', 25, 'mail.from.domain', # 'Your Account', 'Your Password', :cram_md5) # class SMTP < Protocol Revision = %q$Revision$.split[1] # The default SMTP port number, 25. def SMTP.default_port 25 end # The default mail submission port number, 587. def SMTP.default_submission_port 587 end # The default SMTPS port number, 465. def SMTP.default_tls_port 465 end class << self alias default_ssl_port default_tls_port end def SMTP.default_ssl_context OpenSSL::SSL::SSLContext.new end # # Creates a new Net::SMTP object. # # +address+ is the hostname or ip address of your SMTP # server. +port+ is the port to connect to; it defaults to # port 25. # # This method does not open the TCP connection. You can use # SMTP.start instead of SMTP.new if you want to do everything # at once. Otherwise, follow SMTP.new with SMTP#start. # def initialize(address, port = nil) @address = address @port = (port \|\| SMTP.default_port) @esmtp = true @capabilities = nil @socket = nil @started = false @open_timeout = 30 @read_timeout = 60 @error_occurred = false @debug_output = nil @tls = false @starttls = false @ssl_context = nil end # Provide human-readable stringification of class state. def inspect "#<#{self.class} #{@address}:#{@port} started=#{@started}>" end # # Set whether to use ESMTP or not. This should be done before # calling #start. Note that if #start is called in ESMTP mode, # and the connection fails due to a ProtocolError, the SMTP # object will automatically switch to plain SMTP mode and # retry (but not vice versa). # attr_accessor :esmtp # +true+ if the SMTP object uses ESMTP (which it does by default). alias :esmtp? :esmtp # true if server advertises STARTTLS. # You cannot get valid value before opening SMTP session. def capable_starttls? capable?('STARTTLS') end def capable?(key) return nil unless @capabilities @capabilities[key] ? true : false end private :capable? # true if server advertises AUTH PLAIN. # You cannot get valid value before opening SMTP session. def capable_plain_auth? auth_capable?('PLAIN') end # true if server advertises AUTH LOGIN. # You cannot get valid value before opening SMTP session. def capable_login_auth? auth_capable?('LOGIN') end # true if server advertises AUTH CRAM-MD5. # You cannot get valid value before opening SMTP session. def capable_cram_md5_auth? auth_capable?('CRAM-MD5') end def auth_capable?(type) return nil unless @capabilities return false unless @capabilities['AUTH'] @capabilities['AUTH'].include?(type) end private :auth_capable? # Returns supported authentication methods on this server. # You cannot get valid value before opening SMTP session. def capable_auth_types return [] unless @capabilities return [] unless @capabilities['AUTH'] @capabilities['AUTH'] end # true if this object uses SMTP/TLS (SMTPS). def tls? @tls end alias ssl? tls? # Enables SMTP/TLS (SMTPS: SMTP over direct TLS connection) for # this object. Must be called before the connection is established # to have any effect. +context+ is a OpenSSL::SSL::SSLContext object. def enable_tls(context = SMTP.default_ssl_context) raise 'openssl library not installed' unless defined?(OpenSSL) raise ArgumentError, "SMTPS and STARTTLS is exclusive" if @starttls @tls = true @ssl_context = context end alias enable_ssl enable_tls # Disables SMTP/TLS for this object. Must be called before the # connection is established to have any effect. def disable_tls @tls = false @ssl_context = nil end alias disable_ssl disable_tls # Returns truth value if this object uses STARTTLS. # If this object always uses STARTTLS, returns :always. # If this object uses STARTTLS when the server support TLS, returns :auto. def starttls? @starttls end # true if this object uses STARTTLS. def starttls_always? @starttls == :always end # true if this object uses STARTTLS when server advertises STARTTLS. def starttls_auto? @starttls == :auto end # Enables SMTP/TLS (STARTTLS) for this object. # +context+ is a OpenSSL::SSL::SSLContext object. def enable_starttls(context = SMTP.default_ssl_context) raise 'openssl library not installed' unless defined?(OpenSSL) raise ArgumentError, "SMTPS and STARTTLS is exclusive" if @tls @starttls = :always @ssl_context = context end # Enables SMTP/TLS (STARTTLS) for this object if server accepts. # +context+ is a OpenSSL::SSL::SSLContext object. def enable_starttls_auto(context = SMTP.default_ssl_context) raise 'openssl library not installed' unless defined?(OpenSSL) raise ArgumentError, "SMTPS and STARTTLS is exclusive" if @tls @starttls = :auto @ssl_context = context end # Disables SMTP/TLS (STARTTLS) for this object. Must be called # before the connection is established to have any effect. def disable_starttls @starttls = false @ssl_context = nil end # The address of the SMTP server to connect to. attr_reader :address # The port number of the SMTP server to connect to. attr_reader :port # Seconds to wait while attempting to open a connection. # If the connection cannot be opened within this time, a # Net::OpenTimeout is raised. The default value is 30 seconds. attr_accessor :open_timeout # Seconds to wait while reading one block (by one read(2) call). # If the read(2) call does not complete within this time, a # Net::ReadTimeout is raised. The default value is 60 seconds. attr_reader :read_timeout # Set the number of seconds to wait until timing-out a read(2) # call. def read_timeout=(sec) @socket.read_timeout = sec if @socket @read_timeout = sec end # # WARNING: This method causes serious security holes. # Use this method for only debugging. # # Set an output stream for debug logging. # You must call this before #start. # # # example # smtp = Net::SMTP.new(addr, port) # smtp.set_debug_output $stderr # smtp.start do \|smtp\| # .... # end # def debug_output=(arg) @debug_output = arg end alias set_debug_output debug_output= # # SMTP session control # # # Creates a new Net::SMTP object and connects to the server. # # This method is equivalent to: # # Net::SMTP.new(address, port).start(helo_domain, account, password, authtype) # # === Example # # Net::SMTP.start('your.smtp.server') do \|smtp\| # smtp.send_message msgstr, 'from@example.com', ['dest@example.com'] # end # # === Block Usage # # If called with a block, the newly-opened Net::SMTP object is yielded # to the block, and automatically closed when the block finishes. If called # without a block, the newly-opened Net::SMTP object is returned to # the caller, and it is the caller's responsibility to close it when # finished. # # === Parameters # # +address+ is the hostname or ip address of your smtp server. # # +port+ is the port to connect to; it defaults to port 25. # # +helo+ is the _HELO_ _domain_ provided by the client to the # server (see overview comments); it defaults to 'localhost'. # # The remaining arguments are used for SMTP authentication, if required # or desired. +user+ is the account name; +secret+ is your password # or other authentication token; and +authtype+ is the authentication # type, one of :plain, :login, or :cram_md5. See the discussion of # SMTP Authentication in the overview notes. # # === Errors # # This method may raise: # # * Net::SMTPAuthenticationError # * Net::SMTPServerBusy # * Net::SMTPSyntaxError # * Net::SMTPFatalError # * Net::SMTPUnknownError # * Net::OpenTimeout # * Net::ReadTimeout # * IOError # def SMTP.start(address, port = nil, helo = 'localhost', user = nil, secret = nil, authtype = nil, &block) # :yield: smtp new(address, port).start(helo, user, secret, authtype, &block) end # +true+ if the SMTP session has been started. def started? @started end # # Opens a TCP connection and starts the SMTP session. # # === Parameters # # +helo+ is the _HELO_ _domain_ that you'll dispatch mails from; see # the discussion in the overview notes. # # If both of +user+ and +secret+ are given, SMTP authentication # will be attempted using the AUTH command. +authtype+ specifies # the type of authentication to attempt; it must be one of # :login, :plain, and :cram_md5. See the notes on SMTP Authentication # in the overview. # # === Block Usage # # When this methods is called with a block, the newly-started SMTP # object is yielded to the block, and automatically closed after # the block call finishes. Otherwise, it is the caller's # responsibility to close the session when finished. # # === Example # # This is very similar to the class method SMTP.start. # # require 'net/smtp' # smtp = Net::SMTP.new('smtp.mail.server', 25) # smtp.start(helo_domain, account, password, authtype) do \|smtp\| # smtp.send_message msgstr, 'from@example.com', ['dest@example.com'] # end # # The primary use of this method (as opposed to SMTP.start) # is probably to set debugging (#set_debug_output) or ESMTP # (#esmtp=), which must be done before the session is # started. # # === Errors # # If session has already been started, an IOError will be raised. # # This method may raise: # # * Net::SMTPAuthenticationError # * Net::SMTPServerBusy # * Net::SMTPSyntaxError # * Net::SMTPFatalError # * Net::SMTPUnknownError # * Net::OpenTimeout # * Net::ReadTimeout # * IOError # def start(helo = 'localhost', user = nil, secret = nil, authtype = nil) # :yield: smtp if block_given? begin do_start helo, user, secret, authtype return yield(self) ensure do_finish end else do_start helo, user, secret, authtype return self end end # Finishes the SMTP session and closes TCP connection. # Raises IOError if not started. def finish raise IOError, 'not yet started' unless started? do_finish end private def tcp_socket(address, port) TCPSocket.open address, port end def do_start(helo_domain, user, secret, authtype) raise IOError, 'SMTP session already started' if @started if user or secret check_auth_method(authtype \|\| DEFAULT_AUTH_TYPE) check_auth_args user, secret end s = Timeout.timeout(@open_timeout, Net::OpenTimeout) do tcp_socket(@address, @port) end logging "Connection opened: #{@address}:#{@port}" @socket = new_internet_message_io(tls? ? tlsconnect(s) : s) check_response critical { recv_response() } do_helo helo_domain if starttls_always? or (capable_starttls? and starttls_auto?) unless capable_starttls? raise SMTPUnsupportedCommand, "STARTTLS is not supported on this server" end starttls @socket = new_internet_message_io(tlsconnect(s)) # helo response may be different after STARTTLS do_helo helo_domain end authenticate user, secret, (authtype \|\| DEFAULT_AUTH_TYPE) if user @started = true ensure unless @started # authentication failed, cancel connection. s.close if s @socket = nil end end def ssl_socket(socket, context) OpenSSL::SSL::SSLSocket.new socket, context end def tlsconnect(s) verified = false s = ssl_socket(s, @ssl_context) logging "TLS connection started" s.sync_close = true ssl_socket_connect(s, @open_timeout) if @ssl_context.verify_mode != OpenSSL::SSL::VERIFY_NONE s.post_connection_check(@address) end verified = true s ensure s.close unless verified end def new_internet_message_io(s) InternetMessageIO.new(s, read_timeout: @read_timeout, debug_output: @debug_output) end def do_helo(helo_domain) res = @esmtp ? ehlo(helo_domain) : helo(helo_domain) @capabilities = res.capabilities rescue SMTPError if @esmtp @esmtp = false @error_occurred = false retry end raise end def do_finish quit if @socket and not @socket.closed? and not @error_occurred ensure @started = false @error_occurred = false @socket.close if @socket @socket = nil end # # Message Sending # public # # Sends +msgstr+ as a message. Single CR ("\r") and LF ("\n") found # in the +msgstr+, are converted into the CR LF pair. You cannot send a # binary message with this method. +msgstr+ should include both # the message headers and body. # # +from_addr+ is a String representing the source mail address. # # +to_addr+ is a String or Strings or Array of Strings, representing # the destination mail address or addresses. # # === Example # # Net::SMTP.start('smtp.example.com') do \|smtp\| # smtp.send_message msgstr, # 'from@example.com', # ['dest@example.com', 'dest2@example.com'] # end # # === Errors # # This method may raise: # # * Net::SMTPServerBusy # * Net::SMTPSyntaxError # * Net::SMTPFatalError # * Net::SMTPUnknownError # * Net::ReadTimeout # * IOError # def send_message(msgstr, from_addr, to_addrs) raise IOError, 'closed session' unless @socket mailfrom from_addr rcptto_list(to_addrs) {data msgstr} end alias send_mail send_message alias sendmail send_message # obsolete # # Opens a message writer stream and gives it to the block. # The stream is valid only in the block, and has these methods: # # puts(str = ''):: outputs STR and CR LF. # print(str):: outputs STR. # printf(fmt, args):: outputs sprintf(fmt,args). # write(str):: outputs STR and returns the length of written bytes. # <<(str):: outputs STR and returns self. # # If a single CR ("\r") or LF ("\n") is found in the message, # it is converted to the CR LF pair. You cannot send a binary # message with this method. # # === Parameters # # +from_addr+ is a String representing the source mail address. # # +to_addr+ is a String or Strings or Array of Strings, representing # the destination mail address or addresses. # # === Example # # Net::SMTP.start('smtp.example.com', 25) do \|smtp\| # smtp.open_message_stream('from@example.com', ['dest@example.com']) do \|f\| # f.puts 'From: from@example.com' # f.puts 'To: dest@example.com' # f.puts 'Subject: test message' # f.puts # f.puts 'This is a test message.' # end # end # # === Errors # # This method may raise: # # Net::SMTPServerBusy # * Net::SMTPSyntaxError # * Net::SMTPFatalError # * Net::SMTPUnknownError # * Net::ReadTimeout # * IOError # def open_message_stream(from_addr, to_addrs, &block) # :yield: stream raise IOError, 'closed session' unless @socket mailfrom from_addr rcptto_list(to_addrs) {data(&block)} end alias ready open_message_stream # obsolete # # Authentication # public DEFAULT_AUTH_TYPE = :plain def authenticate(user, secret, authtype = DEFAULT_AUTH_TYPE) check_auth_method authtype check_auth_args user, secret send auth_method(authtype), user, secret end def auth_plain(user, secret) check_auth_args user, secret res = critical { get_response('AUTH PLAIN ' + base64_encode("\0#{user}\0#{secret}")) } check_auth_response res res end def auth_login(user, secret) check_auth_args user, secret res = critical { check_auth_continue get_response('AUTH LOGIN') check_auth_continue get_response(base64_encode(user)) get_response(base64_encode(secret)) } check_auth_response res res end def auth_cram_md5(user, secret) check_auth_args user, secret res = critical { res0 = get_response('AUTH CRAM-MD5') check_auth_continue res0 crammed = cram_md5_response(secret, res0.cram_md5_challenge) get_response(base64_encode("#{user} #{crammed}")) } check_auth_response res res end private def check_auth_method(type) unless respond_to?(auth_method(type), true) raise ArgumentError, "wrong authentication type #{type}" end end def auth_method(type) "auth_#{type.to_s.downcase}".intern end def check_auth_args(user, secret, authtype = DEFAULT_AUTH_TYPE) unless user raise ArgumentError, 'SMTP-AUTH requested but missing user name' end unless secret raise ArgumentError, 'SMTP-AUTH requested but missing secret phrase' end end def base64_encode(str) # expects "str" may not become too long [str].pack('m0') end IMASK = 0x36 OMASK = 0x5c # CRAM-MD5: [RFC2195] def cram_md5_response(secret, challenge) tmp = Digest::MD5.digest(cram_secret(secret, IMASK) + challenge) Digest::MD5.hexdigest(cram_secret(secret, OMASK) + tmp) end CRAM_BUFSIZE = 64 def cram_secret(secret, mask) secret = Digest::MD5.digest(secret) if secret.size > CRAM_BUFSIZE buf = secret.ljust(CRAM_BUFSIZE, "\0") 0.upto(buf.size - 1) do \|i\| buf[i] = (buf[i].ord ^ mask).chr end buf end # # SMTP command dispatcher # public # Aborts the current mail transaction def rset getok('RSET') end def starttls getok('STARTTLS') end def helo(domain) getok("HELO #{domain}") end def ehlo(domain) getok("EHLO #{domain}") end def mailfrom(from_addr) getok("MAIL FROM:<#{from_addr}>") end def rcptto_list(to_addrs) raise ArgumentError, 'mail destination not given' if to_addrs.empty? ok_users = [] unknown_users = [] to_addrs.flatten.each do \|addr\| begin rcptto addr rescue SMTPAuthenticationError unknown_users << addr.dump else ok_users << addr end end raise ArgumentError, 'mail destination not given' if ok_users.empty? ret = yield unless unknown_users.empty? raise SMTPAuthenticationError, "failed to deliver for #{unknown_users.join(', ')}" end ret end def rcptto(to_addr) getok("RCPT TO:<#{to_addr}>") end # This method sends a message. # If +msgstr+ is given, sends it as a message. # If block is given, yield a message writer stream. # You must write message before the block is closed. # # # Example 1 (by string) # smtp.data(<<EndMessage) # From: john@example.com # To: betty@example.com # Subject: I found a bug # # Check vm.c:58879. # EndMessage # # # Example 2 (by block) # smtp.data {\|f\| # f.puts "From: john@example.com" # f.puts "To: betty@example.com" # f.puts "Subject: I found a bug" # f.puts "" # f.puts "Check vm.c:58879." # } # def data(msgstr = nil, &block) #:yield: stream if msgstr and block raise ArgumentError, "message and block are exclusive" end unless msgstr or block raise ArgumentError, "message or block is required" end res = critical { check_continue get_response('DATA') socket_sync_bak = @socket.io.sync begin @socket.io.sync = false if msgstr @socket.write_message msgstr else @socket.write_message_by_block(&block) end ensure @socket.io.flush @socket.io.sync = socket_sync_bak end recv_response() } check_response res res end def quit getok('QUIT') end private def validate_line(line) # A bare CR or LF is not allowed in RFC5321. if /[\r\n]/ =~ line raise ArgumentError, "A line must not contain CR or LF" end end def getok(reqline) validate_line reqline res = critical { @socket.writeline reqline recv_response() } check_response res res end def get_response(reqline) validate_line reqline @socket.writeline reqline recv_response() end def recv_response buf = ''.dup while true line = @socket.readline buf << line << "\n" break unless line[3,1] == '-' # "210-PIPELINING" end Response.parse(buf) end def critical return Response.parse('200 dummy reply code') if @error_occurred begin return yield() rescue Exception @error_occurred = true raise end end def check_response(res) unless res.success? raise res.exception_class, res.message end end def check_continue(res) unless res.continue? raise SMTPUnknownError, "could not get 3xx (#{res.status}: #{res.string})" end end def check_auth_response(res) unless res.success? raise SMTPAuthenticationError, res.message end end def check_auth_continue(res) unless res.continue? raise res.exception_class, res.message end end # This class represents a response received by the SMTP server. Instances # of this class are created by the SMTP class; they should not be directly # created by the user. For more information on SMTP responses, view # {Section 4.2 of RFC 5321}[http://tools.ietf.org/html/rfc5321#section-4.2] class Response # Parses the received response and separates the reply code and the human # readable reply text def self.parse(str) new(str[0,3], str) end # Creates a new instance of the Response class and sets the status and # string attributes def initialize(status, string) @status = status @string = string end # The three digit reply code of the SMTP response attr_reader :status # The human readable reply text of the SMTP response attr_reader :string # Takes the first digit of the reply code to determine the status type def status_type_char @status[0, 1] end # Determines whether the response received was a Positive Completion # reply (2xx reply code) def success? status_type_char() == '2' end # Determines whether the response received was a Positive Intermediate # reply (3xx reply code) def continue? status_type_char() == '3' end # The first line of the human readable reply text def message @string.lines.first end # Creates a CRAM-MD5 challenge. You can view more information on CRAM-MD5 # on Wikipedia: https://en.wikipedia.org/wiki/CRAM-MD5 def cram_md5_challenge @string.split(/ /)[1].unpack1('m') end # Returns a hash of the human readable reply text in the response if it # is multiple lines. It does not return the first line. The key of the # hash is the first word the value of the hash is an array with each word # thereafter being a value in the array def capabilities return {} unless @string[3, 1] == '-' h = {} @string.lines.drop(1).each do \|line\| k, v = line[4..-1].chomp.split h[k] = v end h end # Determines whether there was an error and raises the appropriate error # based on the reply code of the response def exception_class case @status when /\A4/ then SMTPServerBusy when /\A50/ then SMTPSyntaxError when /\A53/ then SMTPAuthenticationError when /\A5/ then SMTPFatalError else SMTPUnknownError end end end def logging(msg) @debug_output << msg + "\n" if @debug_output end end # class SMTP SMTPSession = SMTP # :nodoc: end Back

Edit File : smtp.rb | Size : 30.00 KB

# frozen_string_literal: true
# = net/smtp.rb
#
# Copyright (c) 1999-2007 Yukihiro Matsumoto.
#
# Copyright (c) 1999-2007 Minero Aoki.
#
# Written & maintained by Minero Aoki <aamine@loveruby.net>.
#
# Documented by William Webber and Minero Aoki.
#
# This program is free software. You can re-distribute and/or
# modify this program under the same terms as Ruby itself.
#
# $Id$
#
# See Net::SMTP for documentation.
#

require 'net/protocol'
require 'digest/md5'
require 'timeout'
begin
  require 'openssl'
rescue LoadError
end

module Net

# Module mixed in to all SMTP error classes
  module SMTPError
    # This *class* is a module for backward compatibility.
    # In later release, this module becomes a class.
  end

# Represents an SMTP authentication error.
  class SMTPAuthenticationError < ProtoAuthError
    include SMTPError
  end

# Represents SMTP error code 4xx, a temporary error.
  class SMTPServerBusy < ProtoServerError
    include SMTPError
  end

# Represents an SMTP command syntax error (error code 500)
  class SMTPSyntaxError < ProtoSyntaxError
    include SMTPError
  end

# Represents a fatal SMTP error (error code 5xx, except for 500)
  class SMTPFatalError < ProtoFatalError
    include SMTPError
  end

# Unexpected reply code returned from server.
  class SMTPUnknownError < ProtoUnknownError
    include SMTPError
  end

# Command is not supported on server.
  class SMTPUnsupportedCommand < ProtocolError
    include SMTPError
  end

#
  # == What is This Library?
  #
  # This library provides functionality to send internet
  # mail via SMTP, the Simple Mail Transfer Protocol. For details of
  # SMTP itself, see [RFC2821] (http://www.ietf.org/rfc/rfc2821.txt).
  #
  # == What is This Library NOT?
  #
  # This library does NOT provide functions to compose internet mails.
  # You must create them by yourself. If you want better mail support,
  # try RubyMail or TMail or search for alternatives in
  # {RubyGems.org}[https://rubygems.org/] or {The Ruby
  # Toolbox}[https://www.ruby-toolbox.com/].
  #
  # FYI: the official documentation on internet mail is: [RFC2822] (http://www.ietf.org/rfc/rfc2822.txt).
  #
  # == Examples
  #
  # === Sending Messages
  #
  # You must open a connection to an SMTP server before sending messages.
  # The first argument is the address of your SMTP server, and the second
  # argument is the port number. Using SMTP.start with a block is the simplest
  # way to do this. This way, the SMTP connection is closed automatically
  # after the block is executed.
  #
  #     require 'net/smtp'
  #     Net::SMTP.start('your.smtp.server', 25) do |smtp|
  #       # Use the SMTP object smtp only in this block.
  #     end
  #
  # Replace 'your.smtp.server' with your SMTP server. Normally
  # your system manager or internet provider supplies a server
  # for you.
  #
  # Then you can send messages.
  #
  #     msgstr = <<END_OF_MESSAGE
  #     From: Your Name <your@mail.address>
  #     To: Destination Address <someone@example.com>
  #     Subject: test message
  #     Date: Sat, 23 Jun 2001 16:26:43 +0900
  #     Message-Id: <unique.message.id.string@example.com>
  #
  #     This is a test message.
  #     END_OF_MESSAGE
  #
  #     require 'net/smtp'
  #     Net::SMTP.start('your.smtp.server', 25) do |smtp|
  #       smtp.send_message msgstr,
  #                         'your@mail.address',
  #                         'his_address@example.com'
  #     end
  #
  # === Closing the Session
  #
  # You MUST close the SMTP session after sending messages, by calling
  # the #finish method:
  #
  #     # using SMTP#finish
  #     smtp = Net::SMTP.start('your.smtp.server', 25)
  #     smtp.send_message msgstr, 'from@address', 'to@address'
  #     smtp.finish
  #
  # You can also use the block form of SMTP.start/SMTP#start.  This closes
  # the SMTP session automatically:
  #
  #     # using block form of SMTP.start
  #     Net::SMTP.start('your.smtp.server', 25) do |smtp|
  #       smtp.send_message msgstr, 'from@address', 'to@address'
  #     end
  #
  # I strongly recommend this scheme.  This form is simpler and more robust.
  #
  # === HELO domain
  #
  # In almost all situations, you must provide a third argument
  # to SMTP.start/SMTP#start. This is the domain name which you are on
  # (the host to send mail from). It is called the "HELO domain".
  # The SMTP server will judge whether it should send or reject
  # the SMTP session by inspecting the HELO domain.
  #
  #     Net::SMTP.start('your.smtp.server', 25,
  #                     'mail.from.domain') { |smtp| ... }
  #
  # === SMTP Authentication
  #
  # The Net::SMTP class supports three authentication schemes;
  # PLAIN, LOGIN and CRAM MD5.  (SMTP Authentication: [RFC2554])
  # To use SMTP authentication, pass extra arguments to
  # SMTP.start/SMTP#start.
  #
  #     # PLAIN
  #     Net::SMTP.start('your.smtp.server', 25, 'mail.from.domain',
  #                     'Your Account', 'Your Password', :plain)
  #     # LOGIN
  #     Net::SMTP.start('your.smtp.server', 25, 'mail.from.domain',
  #                     'Your Account', 'Your Password', :login)
  #
  #     # CRAM MD5
  #     Net::SMTP.start('your.smtp.server', 25, 'mail.from.domain',
  #                     'Your Account', 'Your Password', :cram_md5)
  #
  class SMTP < Protocol

Revision = %q$Revision$.split[1]

# The default SMTP port number, 25.
    def SMTP.default_port
      25
    end

# The default mail submission port number, 587.
    def SMTP.default_submission_port
      587
    end

# The default SMTPS port number, 465.
    def SMTP.default_tls_port
      465
    end

class << self
      alias default_ssl_port default_tls_port
    end

def SMTP.default_ssl_context
      OpenSSL::SSL::SSLContext.new
    end

#
    # Creates a new Net::SMTP object.
    #
    # +address+ is the hostname or ip address of your SMTP
    # server.  +port+ is the port to connect to; it defaults to
    # port 25.
    #
    # This method does not open the TCP connection.  You can use
    # SMTP.start instead of SMTP.new if you want to do everything
    # at once.  Otherwise, follow SMTP.new with SMTP#start.
    #
    def initialize(address, port = nil)
      @address = address
      @port = (port || SMTP.default_port)
      @esmtp = true
      @capabilities = nil
      @socket = nil
      @started = false
      @open_timeout = 30
      @read_timeout = 60
      @error_occurred = false
      @debug_output = nil
      @tls = false
      @starttls = false
      @ssl_context = nil
    end

# Provide human-readable stringification of class state.
    def inspect
      "#<#{self.class} #{@address}:#{@port} started=#{@started}>"
    end

#
    # Set whether to use ESMTP or not.  This should be done before
    # calling #start.  Note that if #start is called in ESMTP mode,
    # and the connection fails due to a ProtocolError, the SMTP
    # object will automatically switch to plain SMTP mode and
    # retry (but not vice versa).
    #
    attr_accessor :esmtp

# +true+ if the SMTP object uses ESMTP (which it does by default).
    alias :esmtp? :esmtp

# true if server advertises STARTTLS.
    # You cannot get valid value before opening SMTP session.
    def capable_starttls?
      capable?('STARTTLS')
    end

def capable?(key)
      return nil unless @capabilities
      @capabilities[key] ? true : false
    end
    private :capable?

# true if server advertises AUTH PLAIN.
    # You cannot get valid value before opening SMTP session.
    def capable_plain_auth?
      auth_capable?('PLAIN')
    end

# true if server advertises AUTH LOGIN.
    # You cannot get valid value before opening SMTP session.
    def capable_login_auth?
      auth_capable?('LOGIN')
    end

# true if server advertises AUTH CRAM-MD5.
    # You cannot get valid value before opening SMTP session.
    def capable_cram_md5_auth?
      auth_capable?('CRAM-MD5')
    end

def auth_capable?(type)
      return nil unless @capabilities
      return false unless @capabilities['AUTH']
      @capabilities['AUTH'].include?(type)
    end
    private :auth_capable?

# Returns supported authentication methods on this server.
    # You cannot get valid value before opening SMTP session.
    def capable_auth_types
      return [] unless @capabilities
      return [] unless @capabilities['AUTH']
      @capabilities['AUTH']
    end

# true if this object uses SMTP/TLS (SMTPS).
    def tls?
      @tls
    end

alias ssl? tls?

# Enables SMTP/TLS (SMTPS: SMTP over direct TLS connection) for
    # this object.  Must be called before the connection is established
    # to have any effect.  +context+ is a OpenSSL::SSL::SSLContext object.
    def enable_tls(context = SMTP.default_ssl_context)
      raise 'openssl library not installed' unless defined?(OpenSSL)
      raise ArgumentError, "SMTPS and STARTTLS is exclusive" if @starttls
      @tls = true
      @ssl_context = context
    end

alias enable_ssl enable_tls

# Disables SMTP/TLS for this object.  Must be called before the
    # connection is established to have any effect.
    def disable_tls
      @tls = false
      @ssl_context = nil
    end

alias disable_ssl disable_tls

# Returns truth value if this object uses STARTTLS.
    # If this object always uses STARTTLS, returns :always.
    # If this object uses STARTTLS when the server support TLS, returns :auto.
    def starttls?
      @starttls
    end

# true if this object uses STARTTLS.
    def starttls_always?
      @starttls == :always
    end

# true if this object uses STARTTLS when server advertises STARTTLS.
    def starttls_auto?
      @starttls == :auto
    end

# Enables SMTP/TLS (STARTTLS) for this object.
    # +context+ is a OpenSSL::SSL::SSLContext object.
    def enable_starttls(context = SMTP.default_ssl_context)
      raise 'openssl library not installed' unless defined?(OpenSSL)
      raise ArgumentError, "SMTPS and STARTTLS is exclusive" if @tls
      @starttls = :always
      @ssl_context = context
    end

# Enables SMTP/TLS (STARTTLS) for this object if server accepts.
    # +context+ is a OpenSSL::SSL::SSLContext object.
    def enable_starttls_auto(context = SMTP.default_ssl_context)
      raise 'openssl library not installed' unless defined?(OpenSSL)
      raise ArgumentError, "SMTPS and STARTTLS is exclusive" if @tls
      @starttls = :auto
      @ssl_context = context
    end

# Disables SMTP/TLS (STARTTLS) for this object.  Must be called
    # before the connection is established to have any effect.
    def disable_starttls
      @starttls = false
      @ssl_context = nil
    end

# The address of the SMTP server to connect to.
    attr_reader :address

# The port number of the SMTP server to connect to.
    attr_reader :port

# Seconds to wait while attempting to open a connection.
    # If the connection cannot be opened within this time, a
    # Net::OpenTimeout is raised. The default value is 30 seconds.
    attr_accessor :open_timeout

# Seconds to wait while reading one block (by one read(2) call).
    # If the read(2) call does not complete within this time, a
    # Net::ReadTimeout is raised. The default value is 60 seconds.
    attr_reader :read_timeout

# Set the number of seconds to wait until timing-out a read(2)
    # call.
    def read_timeout=(sec)
      @socket.read_timeout = sec if @socket
      @read_timeout = sec
    end

#
    # WARNING: This method causes serious security holes.
    # Use this method for only debugging.
    #
    # Set an output stream for debug logging.
    # You must call this before #start.
    #
    #   # example
    #   smtp = Net::SMTP.new(addr, port)
    #   smtp.set_debug_output $stderr
    #   smtp.start do |smtp|
    #     ....
    #   end
    #
    def debug_output=(arg)
      @debug_output = arg
    end

alias set_debug_output debug_output=

#
    # SMTP session control
    #

#
    # Creates a new Net::SMTP object and connects to the server.
    #
    # This method is equivalent to:
    #
    #   Net::SMTP.new(address, port).start(helo_domain, account, password, authtype)
    #
    # === Example
    #
    #     Net::SMTP.start('your.smtp.server') do |smtp|
    #       smtp.send_message msgstr, 'from@example.com', ['dest@example.com']
    #     end
    #
    # === Block Usage
    #
    # If called with a block, the newly-opened Net::SMTP object is yielded
    # to the block, and automatically closed when the block finishes.  If called
    # without a block, the newly-opened Net::SMTP object is returned to
    # the caller, and it is the caller's responsibility to close it when
    # finished.
    #
    # === Parameters
    #
    # +address+ is the hostname or ip address of your smtp server.
    #
    # +port+ is the port to connect to; it defaults to port 25.
    #
    # +helo+ is the _HELO_ _domain_ provided by the client to the
    # server (see overview comments); it defaults to 'localhost'.
    #
    # The remaining arguments are used for SMTP authentication, if required
    # or desired.  +user+ is the account name; +secret+ is your password
    # or other authentication token; and +authtype+ is the authentication
    # type, one of :plain, :login, or :cram_md5.  See the discussion of
    # SMTP Authentication in the overview notes.
    #
    # === Errors
    #
    # This method may raise:
    #
    # * Net::SMTPAuthenticationError
    # * Net::SMTPServerBusy
    # * Net::SMTPSyntaxError
    # * Net::SMTPFatalError
    # * Net::SMTPUnknownError
    # * Net::OpenTimeout
    # * Net::ReadTimeout
    # * IOError
    #
    def SMTP.start(address, port = nil, helo = 'localhost',
                   user = nil, secret = nil, authtype = nil,
                   &block)   # :yield: smtp
      new(address, port).start(helo, user, secret, authtype, &block)
    end

# +true+ if the SMTP session has been started.
    def started?
      @started
    end

#
    # Opens a TCP connection and starts the SMTP session.
    #
    # === Parameters
    #
    # +helo+ is the _HELO_ _domain_ that you'll dispatch mails from; see
    # the discussion in the overview notes.
    #
    # If both of +user+ and +secret+ are given, SMTP authentication
    # will be attempted using the AUTH command.  +authtype+ specifies
    # the type of authentication to attempt; it must be one of
    # :login, :plain, and :cram_md5.  See the notes on SMTP Authentication
    # in the overview.
    #
    # === Block Usage
    #
    # When this methods is called with a block, the newly-started SMTP
    # object is yielded to the block, and automatically closed after
    # the block call finishes.  Otherwise, it is the caller's
    # responsibility to close the session when finished.
    #
    # === Example
    #
    # This is very similar to the class method SMTP.start.
    #
    #     require 'net/smtp'
    #     smtp = Net::SMTP.new('smtp.mail.server', 25)
    #     smtp.start(helo_domain, account, password, authtype) do |smtp|
    #       smtp.send_message msgstr, 'from@example.com', ['dest@example.com']
    #     end
    #
    # The primary use of this method (as opposed to SMTP.start)
    # is probably to set debugging (#set_debug_output) or ESMTP
    # (#esmtp=), which must be done before the session is
    # started.
    #
    # === Errors
    #
    # If session has already been started, an IOError will be raised.
    #
    # This method may raise:
    #
    # * Net::SMTPAuthenticationError
    # * Net::SMTPServerBusy
    # * Net::SMTPSyntaxError
    # * Net::SMTPFatalError
    # * Net::SMTPUnknownError
    # * Net::OpenTimeout
    # * Net::ReadTimeout
    # * IOError
    #
    def start(helo = 'localhost',
              user = nil, secret = nil, authtype = nil)   # :yield: smtp
      if block_given?
        begin
          do_start helo, user, secret, authtype
          return yield(self)
        ensure
          do_finish
        end
      else
        do_start helo, user, secret, authtype
        return self
      end
    end

# Finishes the SMTP session and closes TCP connection.
    # Raises IOError if not started.
    def finish
      raise IOError, 'not yet started' unless started?
      do_finish
    end

private

def tcp_socket(address, port)
      TCPSocket.open address, port
    end

def do_start(helo_domain, user, secret, authtype)
      raise IOError, 'SMTP session already started' if @started
      if user or secret
        check_auth_method(authtype || DEFAULT_AUTH_TYPE)
        check_auth_args user, secret
      end
      s = Timeout.timeout(@open_timeout, Net::OpenTimeout) do
        tcp_socket(@address, @port)
      end
      logging "Connection opened: #{@address}:#{@port}"
      @socket = new_internet_message_io(tls? ? tlsconnect(s) : s)
      check_response critical { recv_response() }
      do_helo helo_domain
      if starttls_always? or (capable_starttls? and starttls_auto?)
        unless capable_starttls?
          raise SMTPUnsupportedCommand,
              "STARTTLS is not supported on this server"
        end
        starttls
        @socket = new_internet_message_io(tlsconnect(s))
        # helo response may be different after STARTTLS
        do_helo helo_domain
      end
      authenticate user, secret, (authtype || DEFAULT_AUTH_TYPE) if user
      @started = true
    ensure
      unless @started
        # authentication failed, cancel connection.
        s.close if s
        @socket = nil
      end
    end

def ssl_socket(socket, context)
      OpenSSL::SSL::SSLSocket.new socket, context
    end

def tlsconnect(s)
      verified = false
      s = ssl_socket(s, @ssl_context)
      logging "TLS connection started"
      s.sync_close = true
      ssl_socket_connect(s, @open_timeout)
      if @ssl_context.verify_mode != OpenSSL::SSL::VERIFY_NONE
        s.post_connection_check(@address)
      end
      verified = true
      s
    ensure
      s.close unless verified
    end

def new_internet_message_io(s)
      InternetMessageIO.new(s, read_timeout: @read_timeout,
                            debug_output: @debug_output)
    end

def do_helo(helo_domain)
      res = @esmtp ? ehlo(helo_domain) : helo(helo_domain)
      @capabilities = res.capabilities
    rescue SMTPError
      if @esmtp
        @esmtp = false
        @error_occurred = false
        retry
      end
      raise
    end

def do_finish
      quit if @socket and not @socket.closed? and not @error_occurred
    ensure
      @started = false
      @error_occurred = false
      @socket.close if @socket
      @socket = nil
    end

#
    # Message Sending
    #

public

#
    # Sends +msgstr+ as a message.  Single CR ("\r") and LF ("\n") found
    # in the +msgstr+, are converted into the CR LF pair.  You cannot send a
    # binary message with this method. +msgstr+ should include both
    # the message headers and body.
    #
    # +from_addr+ is a String representing the source mail address.
    #
    # +to_addr+ is a String or Strings or Array of Strings, representing
    # the destination mail address or addresses.
    #
    # === Example
    #
    #     Net::SMTP.start('smtp.example.com') do |smtp|
    #       smtp.send_message msgstr,
    #                         'from@example.com',
    #                         ['dest@example.com', 'dest2@example.com']
    #     end
    #
    # === Errors
    #
    # This method may raise:
    #
    # * Net::SMTPServerBusy
    # * Net::SMTPSyntaxError
    # * Net::SMTPFatalError
    # * Net::SMTPUnknownError
    # * Net::ReadTimeout
    # * IOError
    #
    def send_message(msgstr, from_addr, *to_addrs)
      raise IOError, 'closed session' unless @socket
      mailfrom from_addr
      rcptto_list(to_addrs) {data msgstr}
    end

alias send_mail send_message
    alias sendmail send_message   # obsolete

#
    # Opens a message writer stream and gives it to the block.
    # The stream is valid only in the block, and has these methods:
    #
    # puts(str = '')::       outputs STR and CR LF.
    # print(str)::           outputs STR.
    # printf(fmt, *args)::   outputs sprintf(fmt,*args).
    # write(str)::           outputs STR and returns the length of written bytes.
    # <<(str)::              outputs STR and returns self.
    #
    # If a single CR ("\r") or LF ("\n") is found in the message,
    # it is converted to the CR LF pair.  You cannot send a binary
    # message with this method.
    #
    # === Parameters
    #
    # +from_addr+ is a String representing the source mail address.
    #
    # +to_addr+ is a String or Strings or Array of Strings, representing
    # the destination mail address or addresses.
    #
    # === Example
    #
    #     Net::SMTP.start('smtp.example.com', 25) do |smtp|
    #       smtp.open_message_stream('from@example.com', ['dest@example.com']) do |f|
    #         f.puts 'From: from@example.com'
    #         f.puts 'To: dest@example.com'
    #         f.puts 'Subject: test message'
    #         f.puts
    #         f.puts 'This is a test message.'
    #       end
    #     end
    #
    # === Errors
    #
    # This method may raise:
    #
    # * Net::SMTPServerBusy
    # * Net::SMTPSyntaxError
    # * Net::SMTPFatalError
    # * Net::SMTPUnknownError
    # * Net::ReadTimeout
    # * IOError
    #
    def open_message_stream(from_addr, *to_addrs, &block)   # :yield: stream
      raise IOError, 'closed session' unless @socket
      mailfrom from_addr
      rcptto_list(to_addrs) {data(&block)}
    end

alias ready open_message_stream   # obsolete

#
    # Authentication
    #

public

DEFAULT_AUTH_TYPE = :plain

def authenticate(user, secret, authtype = DEFAULT_AUTH_TYPE)
      check_auth_method authtype
      check_auth_args user, secret
      send auth_method(authtype), user, secret
    end

def auth_plain(user, secret)
      check_auth_args user, secret
      res = critical {
        get_response('AUTH PLAIN ' + base64_encode("\0#{user}\0#{secret}"))
      }
      check_auth_response res
      res
    end

def auth_login(user, secret)
      check_auth_args user, secret
      res = critical {
        check_auth_continue get_response('AUTH LOGIN')
        check_auth_continue get_response(base64_encode(user))
        get_response(base64_encode(secret))
      }
      check_auth_response res
      res
    end

def auth_cram_md5(user, secret)
      check_auth_args user, secret
      res = critical {
        res0 = get_response('AUTH CRAM-MD5')
        check_auth_continue res0
        crammed = cram_md5_response(secret, res0.cram_md5_challenge)
        get_response(base64_encode("#{user} #{crammed}"))
      }
      check_auth_response res
      res
    end

private

def check_auth_method(type)
      unless respond_to?(auth_method(type), true)
        raise ArgumentError, "wrong authentication type #{type}"
      end
    end

def auth_method(type)
      "auth_#{type.to_s.downcase}".intern
    end

def check_auth_args(user, secret, authtype = DEFAULT_AUTH_TYPE)
      unless user
        raise ArgumentError, 'SMTP-AUTH requested but missing user name'
      end
      unless secret
        raise ArgumentError, 'SMTP-AUTH requested but missing secret phrase'
      end
    end

def base64_encode(str)
      # expects "str" may not become too long
      [str].pack('m0')
    end

IMASK = 0x36
    OMASK = 0x5c

# CRAM-MD5: [RFC2195]
    def cram_md5_response(secret, challenge)
      tmp = Digest::MD5.digest(cram_secret(secret, IMASK) + challenge)
      Digest::MD5.hexdigest(cram_secret(secret, OMASK) + tmp)
    end

CRAM_BUFSIZE = 64

def cram_secret(secret, mask)
      secret = Digest::MD5.digest(secret) if secret.size > CRAM_BUFSIZE
      buf = secret.ljust(CRAM_BUFSIZE, "\0")
      0.upto(buf.size - 1) do |i|
        buf[i] = (buf[i].ord ^ mask).chr
      end
      buf
    end

#
    # SMTP command dispatcher
    #

public

# Aborts the current mail transaction

def rset
      getok('RSET')
    end

def starttls
      getok('STARTTLS')
    end

def helo(domain)
      getok("HELO #{domain}")
    end

def ehlo(domain)
      getok("EHLO #{domain}")
    end

def mailfrom(from_addr)
      getok("MAIL FROM:<#{from_addr}>")
    end

def rcptto_list(to_addrs)
      raise ArgumentError, 'mail destination not given' if to_addrs.empty?
      ok_users = []
      unknown_users = []
      to_addrs.flatten.each do |addr|
        begin
          rcptto addr
        rescue SMTPAuthenticationError
          unknown_users << addr.dump
        else
          ok_users << addr
        end
      end
      raise ArgumentError, 'mail destination not given' if ok_users.empty?
      ret = yield
      unless unknown_users.empty?
        raise SMTPAuthenticationError, "failed to deliver for #{unknown_users.join(', ')}"
      end
      ret
    end

def rcptto(to_addr)
      getok("RCPT TO:<#{to_addr}>")
    end

# This method sends a message.
    # If +msgstr+ is given, sends it as a message.
    # If block is given, yield a message writer stream.
    # You must write message before the block is closed.
    #
    #   # Example 1 (by string)
    #   smtp.data(<<EndMessage)
    #   From: john@example.com
    #   To: betty@example.com
    #   Subject: I found a bug
    #
    #   Check vm.c:58879.
    #   EndMessage
    #
    #   # Example 2 (by block)
    #   smtp.data {|f|
    #     f.puts "From: john@example.com"
    #     f.puts "To: betty@example.com"
    #     f.puts "Subject: I found a bug"
    #     f.puts ""
    #     f.puts "Check vm.c:58879."
    #   }
    #
    def data(msgstr = nil, &block)   #:yield: stream
      if msgstr and block
        raise ArgumentError, "message and block are exclusive"
      end
      unless msgstr or block
        raise ArgumentError, "message or block is required"
      end
      res = critical {
        check_continue get_response('DATA')
        socket_sync_bak = @socket.io.sync
        begin
          @socket.io.sync = false
          if msgstr
            @socket.write_message msgstr
          else
            @socket.write_message_by_block(&block)
          end
        ensure
          @socket.io.flush
          @socket.io.sync = socket_sync_bak
        end
        recv_response()
      }
      check_response res
      res
    end

def quit
      getok('QUIT')
    end

private

def validate_line(line)
      # A bare CR or LF is not allowed in RFC5321.
      if /[\r\n]/ =~ line
        raise ArgumentError, "A line must not contain CR or LF"
      end
    end

def getok(reqline)
      validate_line reqline
      res = critical {
        @socket.writeline reqline
        recv_response()
      }
      check_response res
      res
    end

def get_response(reqline)
      validate_line reqline
      @socket.writeline reqline
      recv_response()
    end

def recv_response
      buf = ''.dup
      while true
        line = @socket.readline
        buf << line << "\n"
        break unless line[3,1] == '-'   # "210-PIPELINING"
      end
      Response.parse(buf)
    end

def critical
      return Response.parse('200 dummy reply code') if @error_occurred
      begin
        return yield()
      rescue Exception
        @error_occurred = true
        raise
      end
    end

def check_response(res)
      unless res.success?
        raise res.exception_class, res.message
      end
    end

def check_continue(res)
      unless res.continue?
        raise SMTPUnknownError, "could not get 3xx (#{res.status}: #{res.string})"
      end
    end

def check_auth_response(res)
      unless res.success?
        raise SMTPAuthenticationError, res.message
      end
    end

def check_auth_continue(res)
      unless res.continue?
        raise res.exception_class, res.message
      end
    end

# This class represents a response received by the SMTP server. Instances
    # of this class are created by the SMTP class; they should not be directly
    # created by the user. For more information on SMTP responses, view
    # {Section 4.2 of RFC 5321}[http://tools.ietf.org/html/rfc5321#section-4.2]
    class Response
      # Parses the received response and separates the reply code and the human
      # readable reply text
      def self.parse(str)
        new(str[0,3], str)
      end

# Creates a new instance of the Response class and sets the status and
      # string attributes
      def initialize(status, string)
        @status = status
        @string = string
      end

# The three digit reply code of the SMTP response
      attr_reader :status

# The human readable reply text of the SMTP response
      attr_reader :string

# Takes the first digit of the reply code to determine the status type
      def status_type_char
        @status[0, 1]
      end

# Determines whether the response received was a Positive Completion
      # reply (2xx reply code)
      def success?
        status_type_char() == '2'
      end

# Determines whether the response received was a Positive Intermediate
      # reply (3xx reply code)
      def continue?
        status_type_char() == '3'
      end

# The first line of the human readable reply text
      def message
        @string.lines.first
      end

# Creates a CRAM-MD5 challenge. You can view more information on CRAM-MD5
      # on Wikipedia: https://en.wikipedia.org/wiki/CRAM-MD5
      def cram_md5_challenge
        @string.split(/ /)[1].unpack1('m')
      end

# Returns a hash of the human readable reply text in the response if it
      # is multiple lines. It does not return the first line. The key of the
      # hash is the first word the value of the hash is an array with each word
      # thereafter being a value in the array
      def capabilities
        return {} unless @string[3, 1] == '-'
        h = {}
        @string.lines.drop(1).each do |line|
          k, *v = line[4..-1].chomp.split
          h[k] = v
        end
        h
      end

# Determines whether there was an error and raises the appropriate error
      # based on the reply code of the response
      def exception_class
        case @status
        when /\A4/  then SMTPServerBusy
        when /\A50/ then SMTPSyntaxError
        when /\A53/ then SMTPAuthenticationError
        when /\A5/  then SMTPFatalError
        else             SMTPUnknownError
        end
      end
    end

def logging(msg)
      @debug_output << msg + "\n" if @debug_output
    end

end   # class SMTP

SMTPSession = SMTP # :nodoc:

end

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