1 \chapter{Mail transfer agents}

2 \label{chap:mail-transfer-agents}

3

4 After having analyzed the market for electronic mail and identified upcoming trends, in the last chapter; this chapter takes a look at \MTA{}s---the intelligent nodes and thus the most important parts of the email infrastructure. The \MTA{}s will be grouped by similarities first. Then the four most popular Free Software \MTA{}s, will be presented to the reader in a short overview and with the most important facts. At the end of this chapter these programs will be compared.

5

6

7

8

9 \section{Types of MTAs}

10 ``Mail transfer agent'' is a term covering a variety of programs. One thing is common to them: they transfer email from one senders to recipients.

11

12 This is how \person{Bryan Costales} defines an \MTA:

13 \begin{quote}

14 A mail transfer agent (\MTA) is a highly specialized program that delivers mail and transports it between machines, like the post office.

15 \hfill\cite{costales97}

16 \end{quote}

17 \name{The Free Dictionary} is a bit more concrete on the term:

18 \begin{quote}

19 Message Transfer Agent - (\MTA, Mail Transfer Agent): Any program responsible for delivering e-mail messages. Upon receiving a message from a Mail User Agent or another \MTA, [...] it [...] delivers it to any local addressees and/or forwards it to other remote \MTA{}s (routing) for delivery to remote recipients.

20 \hfill\citeweb{website:thefreedictionary}

21 \end{quote}

22

23 \person{Dent} and \person{Hafiz} agree \cite[page 19]{dent04} \cite[pages 3-5]{hafiz05}.

24

25 Common to all \MTA{}s is the transport of mail; this is the actual job. Besides this similarity, \MTA{}s can be very different. Some of them have \NAME{POP3} and/or \NAME{IMAP} servers included. Some can fetch mails through these protocols. Others have have all features you can think of. And maybe there are some that do nothing else but transporting email.

26

27 Following is a classification of \MTA{}s into groups of similar programs, regarding what is viewable from the outside.

28

29

30 \subsubsection*{Relay-only MTAs}

31 \label{subsec:relay-only}

32 Also called \name{forwarders}. This is the most simple kind of \MTA. It transfers mail only to defined \name{smart hosts}\footnote{\name{smart host}s are \MTA{}s that receives email and route it to the actual destination}. \name{Relay-only} \MTA{}s do not receive mail from outside the system, and they do not deliver locally. All they do is transfer mail to a specified smart host for further relay.

33

34 Most \MTA{}s can be configured to act as such a \name{forwarder}. But this is usually an additional functionality.

35

36 One uses this kind of \MTA\ to give a system the possibility to send mail, without the need to do lots of configuration. In a local network, usually the clients are set up with relay-only \MTA{}s, while there is one mail server that acts as a \name{smart host}. The ``dumb'' clients send mail to this \name{mail server} which does all further work.

37

38 Example programs in that group are: \name{nullmailer}, \name{ssmtp} and \name{esmtp}.

39

40

41 \subsubsection*{Groupware}

42 Normally the term ``groupware'' does not mean one single program, but a suite of programs. They build a framework which is then populated with various modules that provide the actual functionality. Modules for mail transfer, file storage, calendars, resource management, instant messaging, and more, are commonly available.

43

44 These program suites are used if the main work to do is providing integrated communication facilities and team working support for a group of people. Mail transfer is only one part of the problem to solve. The most common scenario are companies. They have \name{groupware} running to provide adequate services for their teams to work efficiently. But one may use \name{groupware} on the home server for his family members also.

45

46 Examples for groupware are: \name{Lotus Notes}, \name{Microsoft Exchange}, \name{OpenGroupware.org}, and \name{eGroupWare}.

47

48

49 \subsubsection*{``Real'' MTAs}

50 There is a third type of \MTA{}s in between the minimalistic \name{relay-only} \MTA{}s and the feature loaded \name{groupware}. Those programs may be named ``real \MTA{}s'', or ``proper \MTA{}s'', though there is no common name. They are what is meant with the term ``mail transfer agent''---programs that transfer mail between hosts.

51

52 Common to them is their focus on transferring email, while being able to act as \name{smart host}s. Their variety ranges from ones mostly restricted to mail transfer (e.g.\ \qmail) to others having interfaces for adding further mail processing modules (e.g.\ \postfix). This group covers everything in between the other two groups.

53

54 ``Real \MTA{}s'' include \sendmail, \exim, \qmail, and \postfix.

55

56

57 \subsubsection*{Other segmenting}

58 \name{Mail transfer agents} can also be split in other ways.

59

60 Due to \sendmail's significance in the early times of email, compatibility interfaces for \sendmail\ are important for \unix\ \MTA{}s. The reason is that many mail applications simply the \sendmail\ \MTA\ to be installed on the system. Being not \emph{sendmail-compatible} may not matter for some fields of action, but makes the program ineligible for serving as a general purpose \MTA\ on \unix\ systems. Hence being sendmail-compatible is a major property of an \MTA. \MTA{}s not having a \emph{sendmail-compatible} interface or not offering it as a compatibility add-on, will not be covered here. One example for such a program is \name{Apache James}. %FIXME: check if correct

61

62 Another separation can be done between \freesw\ \MTA{}s and proprietary ones. Many of the \MTA{}s for \unix\ systems are \freesw. Only these are regarded in the following sections, because comparing \freesw\ with proprietary or commercial software is not what typical users of programs like \masqmail\ do. Comparison with non-free programs may be a point for large \freesw\ projects, trying to step into the business world. Small projects, mostly used by individuals at home, need to be compared against other projects of similar shape. The document is seen from \masqmail's point of view---an \MTA\ for \unix\ systems on home servers and workstations---so non-free software is out of the way.

63

64

65

66

67

68

69 \subsubsection*{\masqmail's position}

70

71 Now, where does \masqmail\ fit in? It is not groupware nor a simple forwarder, thus it belongs to the ``real \MTA{}s''. Additionally it is Free Software and is intended to be sendmail-compatible. This makes it similar to \sendmail, \exim, \qmail, and \postfix. \masqmail\ is intended to be a replacement for those \MTA{}s.

72

73 But: It was not designed to be used as a general replacement for them (see: section \ref{sec:masqmail-target-field}). In fact, \masqmail\ is only a replacement \emph{in some situations}. This primary excludes working in an untrusted environment.

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75

76

77

78

79

80

81

82

83

84 \section{Popular MTAs}

85

86 This section introduces a selection of popular \MTA{}s; they are the most likely substitutes for \masqmail. All are sendmail-compatible ``smart'' \freesw\ \MTA{}s that focus on mail transfer, as is \masqmail.

87

88 The programs chosen to be compared, with each other and with \masqmail, are: \sendmail, \exim, \qmail, and \postfix. They are the most important representatives of the regarded group.

89

90

91 \subsection{Market share analysis}

92 \label{sec:market-share}

93

94 \MTA\ statistics are rare, differ, and good data is hard to collect. These points are bad if one wants good statistics. Thus it is obvious there are only few available.

95

96 Table \ref{tab:mta-market-share} shows the most used \MTA{}s determined by three different statistics. The first was done by \person{Daniel~J.\ Bernstein} (the author of \qmail) in 2001 \cite{bernstein01}. The second is by \person{Simpson} and \person{Bekman} in 2007 and was published on \name{O'ReillyNet} \cite{simpson07}. And the third is from \name{MailRadar.com} with unknown date\footnote{The footer of the website shows ``Copyright 2007'' but more likely does this refer to the whole website.} \citeweb{mailradar:mta-stats}.

97

98 \begin{table}

99 \begin{center}

100 \input{tbl/mta-market-share.tbl}

101 \end{center}

102 \caption{Market share of \MTA{}s}

103 \label{tab:mta-market-share}

104 \end{table}

105

106 All surveys show high market shares for the four \MTA{}s: \sendmail, \exim, \qmail, and \postfix. Only the \name{Microsoft} mail server software and \name{IMail} have comparable large shares. Other Free Software \MTA{}s (\name{smail}, \name{zmailer}, \NAME{MMDF}, \name{courier-mta}) are less important and seldom used.

107

108 The three surveys base on different data. \person{Bernstein} took 1\,000\,000 randomly chosen \NAME{IP} addresses, containing 39\,206 valid hosts; 958 of them accepted \NAME{SMTP} connections. The \person{Simpson} and \person{Bekman} survey used only domains owned by companies; in total 400\,000 hosts. \name{MailRadar} scanned 2\,818\,895 servers, leading to 59\,209 accepted connections.

109

110 All surveys show \sendmail\ to be the most popular \MTA. \postfix, \qmail, and \exim\ are among the best seven in each. \exim\ has slightly smaller shares than the other two. The four together share more than half of the market according to \person{Bernstein} and the \name{MailRadar} statistics. \person{Simpson} and \person{Bekman} have their share to be somewhere between a third and the half. This uncertainty comes from the large amount of unidentifiable \MTA{}s.

111

112 The 22 percent of \name{mail security layers} in the \name{O'Reilly} survey is remarkable. Mail security layers are software guards between the network and the \MTA\ that filter unwanted mail before it reaches the \MTA. This increases security by filtering malicious content and by blocking attacks against the \MTA. This large share may be a result of only regarding business mail servers. The problem concerning the survey is the disguise of the \MTA\ working behind the security layer. It seems wrong to assume equal shares for the \MTA{}s behind the guards as for the unguarded \MTA{}s, because mail security layers will be more often used to guard weak \MTA{}s, as strong ones do not need them so much. This needs to be kept in mind when using the \name{O'Reilly} survey.

113

114 The date of the \name{Mailradar} statistics is not mentioned with it; a mail to \name{Mailradar} asking for information was not replied, unfortunately. However, it seems quite sure that the statistics were published after 2001, caused by the \sendmail\ and \postfix\ shares. But to decide whether before or after the one from \name{O'Reilly} would be just guessing.

115

116

117 \subsection{The four major Free Software MTAs}

118

119 Now follows a small introduction to the four programs chosen for comparison. \masqmail\ is not presented here, as it was already introduced in chapter \ref{chap:introduction}. Longer introductions, including analysis and comparison, were written by \person{Jonathan de Boyne Pollard} \cite{jdebp}.

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121

122

123 \subsubsection*{sendmail}

124 \label{sec:sendmail}

125 \sendmail\ is the best known \MTA, since it was one of the first and surely the one that made \MTA{}s popular. It also was shipped as default \MTA{}s by many vendors of \unix\ systems \citeweb{wikipedia:sendmail}.

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127 The program was written by \person{Eric Allman} as the successor of his program \name{delivermail}. \person{Allman} was not the only one working on the program. Other people developed own versions of it and a variety of flavors came up, especially in the late eighties when Allman was inactive \cite[page~5]{vixie01}.

128

129 \sendmail\ designed to transfer mails between different protocols and networks, this lead to a very flexible, though complex, configuration.

130

131 It was first released with \NAME{BSD} 4.1c in 1983.

132 %fixme: write about its importance and about sendmail-compat

133

134 The latest version is 8.14.3 from May 2008. The program is distributed under the \name{Sendmail License} as both, \freesw\ and proprietary software.

135

136 Further development will go into the project \name{MeTA1} (the former name was \name{sendmail X}) which succeeds \sendmail.

137

138 More information can be found on the \sendmail\ homepage \citeweb{sendmail:homepage} and in the, so called, ``Bat Book'' \cite{costales97}.

139

140

141

142 \subsubsection*{exim}

143 \label{sec:exim}

144 \exim\ was started in 1995 by \person{Philip Hazel} at the \name{University of Cambridge}. It is a fork of \name{smail-3}, and inherited a monolithic architecture similar to \sendmail's. But having no separation of the individual components of the system did not hurt. Its security is quite good \cite{blanco05}.

145

146 \exim\ is highly configurable, especially in the field of mail policies. This makes it easy to specify how mail is routed through the system and who is allowed to send email to whom. Also interfaces to integrate spam and malware checkers are provided by design.

147

148 The program is \freesw, released under the \NAME{GPL}. The latest stable version is 4.69 from December 2007.

149

150 One finds \exim\ on its homepage \citeweb{exim:homepage}. The standard literature is \person{Hazel}'s \exim\ book \cite{hazel01}.

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152

153

154 \subsubsection*{qmail}

155 \label{sec:qmail}

156 \qmail\ is seen by its community as ``a modern SMTP server which makes sendmail obsolete'' \citeweb{qmail:homepage2}. It was written by \person{Daniel~J.\ Bernstein} starting in 1995. His primary goal was to create a secure \MTA\ to replace the popular, but vulnerable, \sendmail. His own words are: ``This is why I started writing qmail: I was sick of the security holes in sendmail and other \MTA{}s.'' \citeweb{qmail:homepage1}.

157

158 \qmail\ first introduced many innovative concepts in \MTA\ design. The most obvious contrast to \sendmail\ and \exim\ is its modular design. But \qmail\ was not the first modular \MTA. \NAME{MMDF}, which predates even \sendmail, was modular too. Regardless of \NAME{MMDF}'s modular architecture, \qmail\ is generally seen as the first security-aware \MTA\ \citeweb{wikipedia:qmail}.

159

160 The latest release of \qmail\ is version 1.03 from July 1998. In November 2007, afterwards, \qmail's source was put into the \name{public domain}. This makes it Free Software.

161

162 Because of \person{Bernstein}'s inactivity though changing requirements since 1998, ``[a] motley krewe of qmail contributors (see the README) has put together a netqmail-1.06 distribution of qmail. It is derived from Daniel Bernstein's qmail-1.03 plus bug fixes, a few feature enhancements, and some documentation.'' \citeweb{netqmail:homepage}.

163

164 \qmail's homepages are \citeweb{qmail:homepage1} and \citeweb{qmail:homepage2}. The best book about \qmail, from \person{Bernstein}'s view, is \person{Dave Sill}'s handbook \cite{sill02}. His free available guide ``Life with qmail'' is another valuable source \cite{lifewithqmail}.

165

166

167

168 \subsubsection*{postfix}

169 \label{sec:postfix}

170 The \postfix\ project started in 1999 at \name{IBM research}, then called \name{VMailer} or \name{IBM Secure Mailer}. \person{Wietse Venema}'s program ``attempts to be fast, easy to administer, and secure. The outside has a definite Sendmail-ish flavor, but the inside is completely different.''\citeweb{postfix:homepage} In fact, \postfix\ was mainly designed after qmail's architecture to gain security. But in contrast to \qmail\ it aims much more on being fast and full-featured.

171

172 Today \postfix\ is taken by many \unix\ systems and \gnulinux\ distributions as default \MTA.

173

174 The latest stable version is numbered 2.5.6 from December 2008. \postfix\ is covered by the \name{IBM Public License 1.0} which is a \freesw\ license.

175

176 Additional information can be retrieved from the program's homepage \citeweb{postfix:homepage}. \person{Dent}'s \postfix\ book \cite{dent04} claims to be ``the definitive guide'', and it is.

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178

179

180

181

182

183 \section{Comparison of MTAs}

184 \label{sec:mta-comparison}

185

186 This section does not try to provide a throughout \MTA\ comparison, because this is already done by others. Remarkable comparisons are the one by \person{Dan Shearer} \cite{shearer06} and a discussion on the mailing list \name{plug@lists.q-linux.com} \cite{plug:mtas}. Tabular overviews may be found at \citeweb{mailsoftware42}, \citeweb{wikipedia:comparison-of-mail-servers}, and \cite[section 1.9]{lifewithqmail}.

187

188 Here provided is an overview important properties of the four previously introduced \MTA{}s. The data comes from the above stated sources and is collected in table \ref{tab:mta-comparison}\footnote{The lines of code were measured with \person{David~A.\ Wheeler}'s \name{sloccount} \citeweb{sloccount}.}.

189

190 \begin{table}

191 \begin{center}

192 \input{tbl/mta-comparison.tbl}

193 \end{center}

194 \caption{Comparison of \MTA{}s}

195 \label{tab:mta-comparison}

196 \end{table}

197

198

199 \subsubsection*{Architecture}

200

201 Architecture is most important when comparing \MTA{}s. Many other properties of a program depend on its architecture. \person{Munawar Hafiz} \cite{hafiz05} discusses in detail on \MTA\ architecture, comparing \sendmail, \qmail, \postfix, and \name{sendmail X}. \person{Jonathan de Boyne Pollard}'s \MTA\ review \cite{jdebp} is a source too.

202

203 Two different architecture types show off: monolithic and modular \MTA{}s.

204

205 Monolithic \MTA{}s are \sendmail, \name{smail}, \exim, and \masqmail. They all consist of one single \emph{setuid root}\footnote{\emph{setuid root} lets a program run with the rights of its owner, here root. This is considered to be a security risk. Thus it it should be avoided if possible.} binary which does all the work.

206

207 Modular \MTA{}s are \NAME{MMDF}, \qmail, \postfix, and \name{MeTA1}. They consist of several programs, each doing a part of the overall job. The different programs run with the least permissions the need, and \emph{setuid root} can be avoided completely.

208

209 The architecture does not directly define the program's security, but ``[t]he goal of making a software secure can be better achieved by making the design simple and easier to understand and verify'' \cite[chapter 6]{hafiz05}. \exim, though being monolithic, has a fairly clean security record. But it is very hard to keep the security up, as the program growth. \person{Wietse Venema} (the author of \postfix) says, it was the architecture that enabled \postfix\ to grow without running into security problems. \cite[page 13]{venema:postfix-growth}

210

211 The modular design, with each sub-program doing one part of the overall job, conforms to the \name{Unix Philosophy}. The Unix Philosophy \cite{gancarz95} demands ``small is beautiful'' and ``make each program do one thing well''. Monolithic \MTA{}s fail here.

212

213 Today modular \MTA\ architectures are the state-of-the-art.

214

215

216 \subsubsection*{Spam checking and content processing}

217

218 Spam and malware increased during the last years. Today it is important for an \MTA\ to be able to provide checking for bad mail. This can be done by implementing functionality into the \MTA, or by invoking external programs to do this job.

219

220 \sendmail\ invented \name{milter} which is the common abbreviation for the \name{sendmail mail filter} \NAME{API}. It is used to interface external programs of various kind. \postfix\ adopted the \name{milter} interface, but is also able to easily include scanning modules into its modular structure. \qmail\ is pretty old and did not evolve with the changing market situation. Anyhow, its modular structure enables external scanners to be included into \qmail. \exim\ has the advantage that is was designed with the goal to provide extensive scanning facilities. It is therefore very good suited to scan itself or invoke external scanners.

221

222

223 \subsubsection*{Provider independence}

224

225 In chapter \ref{chap:market-analysis}, it was tried to figure out trends and future requirements for \MTA{}s. The four programs are compared on these (possible) future requirements now.

226

227 The first trend was provider independence, requiring easy configuration. \postfix\ seems to do best here. It used primary two configuration files (\path{master.cf} and \path{main.cf}) which are easy to manage. \sendmail\ appears to have a bad position. Its configuration file \path{sendmail.cf} is cryptic and very complex (it has legendary Turing-completeness) thus it needs simplification wrappers around it to provide easier configuration. They exist in form of the \name{m4} macros that generate a \path{sendmail.cf} file. But adjusting the generated result by hand appears to be necessary for non-trivial configurations. \qmail's configuration files are simple, but the whole system is complex to set up; it requires various system users and is hardly usable without applying several patches to add functionality that is required nowadays. \name{netqmail} is the community effort to help in the latter point. \exim\ has only one single configuration file (\path{exim.conf}), but it suffers most from its flexibility---like \sendmail. Flexibility and easy configuration are almost always contrary goals.

228

229 \subsubsection*{Performance}

230

231 As second trend, the decreasing necessity for high performance was identified. This goes along with the move of \MTA{}s from service providers to home servers. \postfix\ focuses much on performance, this might not be an important point in the future. Of course there still will be the need for high performance \MTA{}s, but a growing share of the market will not require high performance. Energy and space efficiency is related to performance; it is a similar goal in a different direction. Optimization, be it for performance or other efficiencies, is often in contrast to simplicity and clarity, which effect security. Optimizing does in most times decrease the simplicity and clarity. Simple \MTA{}s not aiming for high performance are what is needed in future. The simple design of \qmail (\qmail\ is still fast) seems to be a good example.

232

233 \subsubsection*{Security}

234

235 The third trend---even more security awareness---is addressed by each of the four programs. It seems as if all widely used \MTA{}s provide good security nowadays. Even \sendmail\ can be configured to be secure today. But the modular architecture, used by \qmail\ and \postfix, is generally seen to be conceptually more secure, however. \sendmail's creators have started \name{MeTA1}, a modular \MTA\ merging the best of \qmail\ and \postfix, to replace the old \sendmail. It will be interesting to watch \exim's future---will it become modular too?

236

237

238

239

240

241

242 \section{Summary}

243

244 This chapter first took an overview over the field of \MTA{}s. Three major types of \MTA{}s were identified: Relay-only \MTA{}s (also called forwarders), groupware, and the ``real \MTA{}s''. \masqmail\ belongs to the last group, it is additionally sendmail-compatible and Free Software.

245

246 Next a look at the market shares of \MTA{}s was taken and it was seen that four \MTA{}s, that are similar to \masqmail, have high importance: \sendmail, \postfix, \qmail, and \exim. Their combined share is between one third and the half of the market. The rest is split between proprietary \MTA{}s, unknown software behind mail security layers, and a rest of really small market shares.

247

248 Each one of these four major Free Software \MTA{}s was presented afterwards and at the end, these programs were compared on some selected properties.

249

250 Now, the reader should have a general knowledge about the four important \MTA{}s. Further chapters will refer frequently to them.

251

252

253 %fixme: my own poll (?)

254