Microsoft Exchange Server SMTPDiag

Contents
Microsoft Exchange Server SMTPDiag .................................................................1 Contents............................................................................................................................. 2 Microsoft Exchange Server SMTPDiag .................................................................3 SMTPDiag Arguments.................................................................................................... 3 SMTPDiag Results......................................................................................................... SMTPDiag Tests............................................................................................................. ! Co"#right ............................................................................................................... !

Microsoft Exchange Server SMTPDiag

Updated May 3, 2006 Microsoft Exchange Server SMTPDiag is a $iagnostic tool that is use$ to $etermine %hether Sim"le Mail Transfer Protocol &SMTP' an$ Domain (ame S#stem &D(S' are configure$ to relia)l# $eliver mail to an external e*mail a$$ress. This tool automates some of the ste"s $escri)e$ in the follo%ing Microsoft +no%le$ge ,ase articles. 31- 2./ 012 T13 Configure the SMTP Connector to 4in5 to 6nternet Domains in Exchange at htt"377go.microsoft.com7f%lin578lin5i$93:!2;5)i$931- 2.. 1!311-/ <=1R3 Telnet to Port 2! to Test SMTP Communication at htt"377go.microsoft.com7f%lin578lin5i$93:!2;5)i$91!311-. 2:32: / <=1R3 0o% to 1)tain 6nternet Exchanger Recor$s %ith the (Sloo5u".exe >tilit# at htt"377go.microsoft.com7f%lin578lin5i$93:!2;5)i$92:32: . arning ,efore #ou use SMTPDiag/ )e a%are that )ecause the net%or5 traffic coul$ go over an un"rotecte$ net%or5 in unencr#"te$ form/ an anon#mous attac5er on the %ire coul$ "otentiall# interce"t an$ mo$if# the tool. This %oul$ cause incorrect results to )e re"orte$ )# SMTPDiag. ?ou shoul$ consi$er using other sources of information in a$$ition to the re"orts from SMTPDiag %hen #ou ma5e critical trou)leshooting or a$ministrative $ecisions. 6n other %or$s/ $o not rel# com"letel# on this tool for information.

SMTPDiag !rg"#ents
SMTPDiag has t%o re@uire$ an$ t%o o"tional arguments/ an$ )uilt*in 0el". 0el" is $is"la#e$ either )# "rovi$ing no arguments/ or )# using the $% argument. The follo%ing ta)le outlines the arguments an$ corres"on$ing functions $escri)e$ in the 0el".

Usage
SMTPDIAG "sender address" "recipient address" [-d target DNS] [/v]

Argument sen$er a$$ress

=unction Re@uire$. A$$ress of a local mail)ox. >se$ to verif# SMTP su)mission an$ chec5 in)oun$ D(S. Re@uire$. E*mail a$$ress of remote mail)ox #ou are tr#ing to sen$ mail to. >se$ to verif# D(S/ an$ remote mail)ox availa)ilit#. 1"tional. 6P a$$ress of target D(S server to use to loo5 u" remote M< &mail exchange' recor$s for testing. This is fre@uentl# configure$ as an external D(S server in Exchange Server. The external D(S setting is unavaila)le for 6nternet 6nformation Services &66S' SMTP. 1"tional. Dis"la#s a$$itional information a)out each test. Dis"la#s hel".

reci"ient a$$ress

*$ target D(S

7v 78

SMTPDiag &es"'ts
Results are $is"la#e$ in four colors/ as follo%s3 2hite text in$icates action )eing ta5en. Ara# in$icates informational results. Areen in$icates a successful test result. Re$ in$icates a faile$ test result.

SMTPDiag Tests
SMTPDiag issues D(S @ueries using )oth >ser Datagram Protocol &>DP' an$ Transmission Control Protocol &TCP' to vali$ate that the @ueries %ill succee$. Bersions of 2in$o%s )efore MicrosoftC 2in$o%s ServerD 2::3 an$ MicrosoftC 2in$o%sC <P $i$ not su""ort >DP @ueries. 6f TCP @ueries fail/ mail %ill not )e $elivere$ successfull#. The first thing that SMTPDiag $oes after verif#ing s#ntax is to chec5 the Start of Authorit# &S1A' recor$ for the remote a$$ress $omain. The next ste" is to vali$ate that the local $omain M<7A recor$s are resolva)le. This test verifies that the sen$er $omain is vali$ an$ an# )ounces can return to the originating server. This test coul$ fail if the $omain is not resolva)le from insi$e the fire%all. The remote $omain M<7A recor$s are then chec5e$ also. 6f this ste" fails/ mail %ill not route )ecause of issues %ith D(S. At this "oint/ the net%or5 D(S infrastructure must )e investigate$. 2hen all the D(S recor$s have )een successfull# @uerie$/ the tool tries to connect to all the M< &mail exchange' recor$s that %ere "u)lishe$ for the remote $omain on "ort 2!/ an$ tries to $o an E041/ mail from/ rc"t to/ an$ @uit comman$. 6f #ou use the ver)ose &$v' o"tion %hen #ou run the tool/ more information is "rovi$e$ a)out %hat each test is $oing/ as %ell as $etaile$ results of each test ste".

Copyright
The information containe$ in this $ocument re"resents the current vie% of Microsoft Cor"oration on the issues $iscusse$ as of the $ate of "u)lication. ,ecause Microsoft must res"on$ to changing mar5et con$itions/ it shoul$ not )e inter"rete$ to )e a commitment on the "art of Microsoft/ an$ Microsoft cannot guarantee the accurac# of an# information "resente$ after the $ate of "u)lication. This 2hite Pa"er is for informational "ur"oses onl#. M6CR1S1=T MA+ES (1 2ARRA(T6ES/ E<PRESS/ 6MP46ED 1R STAT>T1R?/ AS T1 T0E 6(=1RMAT61( 6( T06S D1C>ME(T. Com"l#ing %ith all a""lica)le co"#right la%s is the res"onsi)ilit# of the user. 2ithout limiting the rights un$er co"#right/ no "art of this $ocument ma# )e re"ro$uce$/ store$ in or intro$uce$ into a retrieval s#stem/ or transmitte$ in an# form or )# an# means &electronic/ mechanical/ "hotoco"#ing/ recor$ing/ or other%ise'/ or for an# "ur"ose/ %ithout the ex"ress %ritten "ermission of Microsoft Cor"oration. Microsoft ma# have "atents/ "atent a""lications/ tra$emar5s/ co"#rights/ or other intellectual "ro"ert# rights covering su)Eect matter in this $ocument. Exce"t as ex"ressl#

6 "rovi$e$ in an# %ritten license agreement from Microsoft/ the furnishing of this $ocument $oes not give #ou an# license to these "atents/ tra$emar5s/ co"#rights/ or other intellectual "ro"ert#. >nless other%ise note$/ the com"anies/ organiFations/ "ro$ucts/ $omain names/ e*mail a$$resses/ logos/ "eo"le/ "laces/ an$ events $e"icte$ in exam"les herein are fictitious. (o association %ith an# real com"an#/ organiFation/ "ro$uct/ $omain name/ e*mail a$$ress/ logo/ "erson/ "lace/ or event is inten$e$ or shoul$ )e inferre$. G 2::. Microsoft Cor"oration. All rights reserve$. Microsoft/ MS*D1S/ 2in$o%s/ 2in$o%s Server/ 2in$o%s Bista/ Active Director#/ ActiveS#nc/ Active</ Entourage/ Excel/ =rontPage/ 0otmail/ HScri"t/ Microsoft Press/ MSD(/ MS(/ 1utloo5/ SharePoint/ Bisual ,asic/ Bisual CII/ Bisual Stu$io/ 2in32/ 2in$o%s Mo)ile/ 2in$o%s (T/ an$ 2in$o%s Server S#stem are either registere$ tra$emar5s or tra$emar5s of Microsoft Cor"oration in the >nite$ States an$7or other countries. All other tra$emar5s are "ro"ert# of their res"ective o%ners.