Question

Exchange Mail Relay

Asked by: dbarman

We have an Exchange 2003 SP2 server.  By looking at the mail queue, it looks like we have a bunch of emails in queue that are VERY unlikley sent by any of our users.  They are going to lots of foreign country domains.  I have run an open relay test at mailradar.com, here are the results:

What do I need to do to get all tests to pass and fix this issue?

P.S. We hare having trouble sending some emails out.  I think the remote servers are thinking we are a spam server or something to that effect.

Port 25 is Open at 75.119.67.138
[Method 0]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:05 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@mailradar.com>
<<< 250 2.1.0 antispam@mailradar.com....Sender OK
>>> RCPT TO: <relaytest@mailradar.com>
<<< 550 5.7.1 Unable to relay for relaytest@mailradar.com
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
[Method 1]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:14 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@mailradar.com>
<<< 250 2.1.0 antispam@mailradar.com....Sender OK
>>> RCPT TO: relaytest@mailradar.com
<<< 550 5.7.1 Unable to relay for relaytest@mailradar.com
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
[Method 2]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:16 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam>
<<< 250 2.1.0 antispam@liptonlawcenter.com....Sender OK
>>> RCPT TO: <relaytest@mailradar.com>
<<< 550 5.7.1 Unable to relay for relaytest@mailradar.com
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
[Method 3]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:17 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <>
<<< 250 2.1.0 <>....Sender OK
>>> RCPT TO: <relaytest@mailradar.com>
<<< 550 5.7.1 Unable to relay for relaytest@mailradar.com
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
[Method 4]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:19 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@[75.119.67.138]>
<<< 250 2.1.0 antispam@[75.119.67.138]....Sender OK
>>> RCPT TO: <relaytest@mailradar.com>
<<< 550 5.7.1 Unable to relay for relaytest@mailradar.com
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
[Method 5]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:21 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@[75.119.67.138]>
<<< 250 2.1.0 antispam@[75.119.67.138]....Sender OK
>>> RCPT TO: <relaytest%mailradar.com@[75.119.67.138]>
<<< 550 5.7.1 Unable to relay for relaytest%mailradar.com@[75.119.67.138]
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
[Method 6]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:22 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@[75.119.67.138]>
<<< 250 2.1.0 antispam@[75.119.67.138]....Sender OK
>>> RCPT TO: <relaytest%mailradar.com.com@[mail.liptonlawcenter.com]>
<<< 501 5.5.4 Invalid Address
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
[Method 7]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:24 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@[75.119.67.138]>
<<< 250 2.1.0 antispam@[75.119.67.138]....Sender OK
>>> RCPT TO: <"relaytest@mailradar.com">
<<< 250 2.1.5 "relaytest@mailradar.com"@liptonlawcenter.com
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST NOT PASSED]
[Method 8]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:25 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@[75.119.67.138]>
<<< 250 2.1.0 antispam@[75.119.67.138]....Sender OK
>>> RCPT TO: <"relaytest%mailradar.com">
<<< 250 2.1.5 "relaytest%mailradar.com"@liptonlawcenter.com
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST NOT PASSED]
[Method 9]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:27 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@[75.119.67.138]>
<<< 250 2.1.0 antispam@[75.119.67.138]....Sender OK
>>> RCPT TO: <relaytest@mailradar.com@[75.119.67.138]>
<<< 501 5.5.4 Invalid Address
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
[Method 10]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:28 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@[75.119.67.138]>
<<< 250 2.1.0 antispam@[75.119.67.138]....Sender OK
>>> RCPT TO: <"relaytest@mailradar.com"@[75.119.67.138]>
<<< 550 5.7.1 Unable to relay for "relaytest@mailradar.com"@[75.119.67.138]
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
[Method 11]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:30 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@[75.119.67.138]>
<<< 250 2.1.0 antispam@[75.119.67.138]....Sender OK
>>> RCPT TO: <relaytest@mailradar.com@mail.liptonlawcenter.com>
<<< 501 5.5.4 Invalid Address
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
[Method 12]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:31 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@[75.119.67.138]>
<<< 250 2.1.0 antispam@[75.119.67.138]....Sender OK
>>> RCPT TO: <@[75.119.67.138]:relaytest@mailradar.com>
<<< 550 5.7.1 Unable to relay for relaytest@mailradar.com
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
[Method 13]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:33 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@[75.119.67.138]>
<<< 250 2.1.0 antispam@[75.119.67.138]....Sender OK
>>> RCPT TO: <@[mail.liptonlawcenter.com]:relaytest@mailradar.com>
<<< 550 5.7.1 Unable to relay for relaytest@mailradar.com
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
[Method 14]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:35 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@[75.119.67.138]>
<<< 250 2.1.0 antispam@[75.119.67.138]....Sender OK
>>> RCPT TO: <mailradar.com!relaytest>
<<< 250 2.1.5 mailradar.com!relaytest@liptonlawcenter.com
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST NOT PASSED]
[Method 15]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:36 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@[75.119.67.138]>
<<< 250 2.1.0 antispam@[75.119.67.138]....Sender OK
>>> RCPT TO: <mailradar.com!relaytest@[75.119.67.138]>
<<< 550 5.7.1 Unable to relay for mailradar.com!relaytest@[75.119.67.138]
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
[Method 16]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:38 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@[75.119.67.138]>
<<< 250 2.1.0 antispam@[75.119.67.138]....Sender OK
>>> RCPT TO: <mailradar.com!relaytest@[mail.liptonlawcenter.com]>
<<< 501 5.5.4 Invalid Address
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
[Method 17]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:39 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@[75.119.67.138]>
<<< 250 2.1.0 antispam@[75.119.67.138]....Sender OK
>>> RCPT TO: <relaytest%mailradar.com@>
<<< 501 5.5.4 Invalid Address
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
[Method 18]
<<< 220 mail.lipton.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at Mon, 15 Jun 2009 14:15:41 -0400
>>> HELO mailradar.com
<<< 250 mail.lipton.local Hello [193.230.245.6]
>>> MAIL FROM: <antispam@[75.119.67.138]>
<<< 250 2.1.0 antispam@[75.119.67.138]....Sender OK
>>> RCPT TO: <relaytest@mailradar.com@>
<<< 501 5.5.4 Invalid Address
>>> QUIT
<<< 221 2.0.0 mail.lipton.local Service closing transmission channel
[TEST PASSED]
All tested completed! Relays accepted by remote host
                                  
1:
2:
3:
4:
5:
6:
7:
8:
9:
10:
11:
12:
13:
14:
15:
16:
17:
18:
19:
20:
21:
22:
23:
24:
25:
26:
27:
28:
29:
30:
31:
32:
33:
34:
35:
36:
37:
38:
39:
40:
41:
42:
43:
44:
45:
46:
47:
48:
49:
50:
51:
52:
53:
54:
55:
56:
57:
58:
59:
60:
61:
62:
63:
64:
65:
66:
67:
68:
69:
70:
71:
72:
73:
74:
75:
76:
77:
78:
79:
80:
81:
82:
83:
84:
85:
86:
87:
88:
89:
90:
91:
92:
93:
94:
95:
96:
97:
98:
99:
100:
101:
102:
103:
104:
105:
106:
107:
108:
109:
110:
111:
112:
113:
114:
115:
116:
117:
118:
119:
120:
121:
122:
123:
124:
125:
126:
127:
128:
129:
130:
131:
132:
133:
134:
135:
136:
137:
138:
139:
140:
141:
142:
143:
144:
145:
146:
147:
148:
149:
150:
151:
152:
153:
154:
155:
156:
157:
158:
159:
160:
161:
162:
163:
164:
165:
166:
167:
168:
169:
170:
171:
172:
173:
174:
175:
176:
177:
178:
179:
180:
181:
182:
183:
184:
185:
186:
187:
188:
189:
190:
191:
192:
193:
194:
195:
196:
197:
198:
199:
200:
201:
202:
203:
204:
205:
206:
207:
208:
209:
210:
211:

Select allOpen in new window

This Question has been solved and asker verified All Experts Exchange premium technology solutions are available to subscription members.

Subscribe now for full access to Experts Exchange and get

Instant Access to this Solution

  • Plus...
  • 30 Day FREE access, no risk, no obligation
  • Collaborate with the world's top tech experts
  • Unlimited access to our exclusive solution database
  • Never be left without tech help again

Subscribe Now

Asked On
2009-06-15 at 11:44:31ID24493209
Tags

Exchange Server 2003

,

relay

Topic

Exchange Email Server

Participating Experts
4
Points
500
Comments
8

Trusted by hundreds of thousands everyday for fast, accurate and reliable tech support.

  • "The time we save is the biggest benefit of Experts Exchange to Warner Bros. What could take multiple guys 2 hours or more each to find is accessed in around 15 minutes on Experts Exchange." Mike Kapnisakis, Warner Bros.
  • "Our team likes having a resource that is more secure than just using Google and most experts using this service really know their stuff. It's nice to look here first versus using Google." Dayna Sellner, Lockheed Martin
  • "Anytime that I've been stumped with a problem, 9 out of 10 times Experts Exchange has either the accepted solution or an open discussion of the potential solution to the problem." Kenny Red, eBay Inc.

See what Experts Exchange can do for you.

Got a question?

We've got the answer.

Experts Exchange has been collecting answers to technology questions since 1996…3 million and counting! If you have a question, chances are we already have your answer.

Screenshot of Experts Exchange Knowledgebase

Need individual assistance?

Our experts are ready to help.

If you can't find the exact answer you're looking for, ask our exclusive community of 50,000 experts. You’ll get a personalized answer from a trusted professional.

Screenshot of Experts Exchange Knowledgebase

Want to learn from the best?

Read articles from industry experts.

Thousands of free tech tips, tricks, how-to’s and tutorials are available in our peer reviewed articles section. See for yourself how smart our experts are, no login required.

Screenshot of an Article

Working on a long term project?

Store your work and research.

Save solutions to your questions, answers you’ve discovered through searching plus helpful articles in your personal knowledgebase for easy future access.

Screenshot of Experts Exchange Knowledgebase

Access the answers to your technology questions today.

Subscribe Now

30-day free trial. Register in 60 seconds.

What Makes Experts Exchange Unique?

Members of the expert community talk about why the experience at Experts Exchange is different than what you will find anywhere else.

Trusted by the world's most respected brands.

image of each brand's logo

Faithfully serving IT professionals since 1996.

Experts Exchange Logo

Try it out and discover for yourself.

Subscribe Now

30-day free trial. Register in 60 seconds.

Related Solutions

  1. Exchange server relaying spam?
    Recently, our ISP notified us that our domain has been reported as sending spam. We have a brand new Exchange 2003 server, which I thought was configured correctly. I looked on dnsstuff and we are listed on 4 blacklists. I have looked through all the questions related to rela...

Free Tech Articles

  1. WARNING: 5 Reasons why you should NEVER fix a computer for free.
    It is in our nature to love the puzzle. We are obsessed. The lot of us. We love puzzles. We love the challenge. We thrive on finding the answer. We hate disarray. It bothers us deep in our soul. W...
  2. SCCM OSD Basic troubleshooting
    SCCM 2007 OSD is a fantastic way to deploy operating systems, however, like most things SCCM issues can sometimes be difficult to resolve due to the sheer volume of logs to sift through and the dispe...
  3. Migrate Small Business Server 2003 to Exchange 2010 and Windows 2008 R2
    This guide is intended to provide step by step instructions on how to migrate from Small Business Server 2003 to Windows 2008 R2 with Exchange 2010. For this migration to work you will need the fo...
  4. Create a Win7 Gadget
    This article shows you how to create a simple "Gadget" -- a sort of mini-application supported by Windows 7 and Vista. Gadgets can be dropped anywhere on the desktop to provide instant information, ...
  5. Outlook continually prompting for username and password
    There have been a lot of questions recently regarding Outlook prompting for a username and password whilst using Exchange 2007. There are a few reasons why this would happen and I will try to cover t...
  6. Backup Exchange 2010 Information Store using Windows Backup
    There seems to be quite a lot of confusion around the ability to backup Exchange 2010 using the built in Windows Backup feature. This stems from the omission of this feature prior to Exchange 2007 s...

Cloud Class Webinars

  1. Avoiding Bugs in Microsoft Access
    Alison Balter takes and in-depth look at avoiding bugs in Access. In this webinar you will learn about using the immediate window to debug your applications, invoking the debugger, using breakpoints to troubleshoot, stepping through code, setting the next statement to execute, ...
  2. Top 10 Best New Features in Visio 2010
    Scott Helmers gives live demonstrations of the top 10 new features in Visio 2010. This webinar will teach you how to create compelling diagrams by adding shapes to the page with a single click, linking the shapes in a diagram to data in Excel (or SQL Server, or SharePoint), ...
  3. IT Consultant Business Secrets Revealed
    Michael Munger, Experts Exchange tech pro and IT consultant, pulls back the curtain on his very successful businesses and answers question on every IT consultant and business owner should know about. He shares secrets on what he did to solve the 5 most common problems in IT, ...
  4. Disaster Recovery and Business Continuity
    Quest CTO, Mike Billon, gives an overview of the steps involved in building a dunamic disaster recovery plan. Through case studies and an examination of software/hardware tooles for monitoring and testing, you'll gain a better understandin of where you are, where you want ...
  5. Organize Your Visio Diagrams with Containers and Lists
    Scott Helmers uses cross functional flowcharts, wireframe diagrams, data graphic legends and seating charts to teach you: how to ustilize all three new structured diagram components in Visio 2010, the best practices for organizeing shapes in previous version of Visio, how to organize ...
  6. How to Us Objects, Properties, Events and Methods in Microsoft Access
    Alison Dalter gives an in-depbth look at objects, properties, events and methods in Microsoft Access. In this webinar you will learn about using the object browser, referring to objects, working with properties and methods, working with object variables, understanding the ...

Join the Community

Give a Little. Get a Lot.

Join the community of experts here and help other tech pros by answering question in your area of expertise. You can earn FREE access to all Experts Exchange's premium features and resources.

Join the Community

Answers

 

by: tercex11Posted on 2009-06-15 at 11:52:35ID: 24631768

Do you have a reverse DNS lookup zone for your email server?
Also you may wnat to create an SPF record if you do not have one.

 

by: bmachtolffPosted on 2009-06-15 at 12:01:52ID: 24631869

Technically, you DO NOT have an open relay, despite those tests failing.  That is because if you look at the addresses that are failing, they are:

"relaytest@mailradar.com"@liptonlawcenter.com
"relaytest%mailradar.com"@liptonlawcenter.com

Basically, your server is appending your own domain name to the malformed username their test submits, which is NOT an open relay.  An open relay would cause your server to accept and deliver mail to another domain and that is NOT happening in this case.

Are the messages in your queue only bounces or actual emails?  Bounces are often seen in queues because each email that ends up at your server addressed to a non-existent user will generate a bounce.  But if the MAIL FROM command gave a fake address, your bounce will sit in the queue for a while before it times out.

- Peter

 

by: bmachtolffPosted on 2009-06-15 at 12:12:48ID: 24631985

This describes your problem exactly and is basically what I said above:
http://support.microsoft.com/kb/304897

And this describes how to fix it, by forcing Exchange to do a directory lookup before accepting mail after a RCPT TO command is given during the SMTP session instead of accepting and appending your local domain name:
http://support.microsoft.com/kb/823866/

- Peter

 

by: kieran_bPosted on 2009-08-02 at 18:01:59ID: 25001359

As for the problem, first problem is that your server is misnamed -> http://www.block.net.au/help/SMTP-Greeting/ - that is probably causing you issues with certain recipients.

Second, applying a recipient filter without tarpitting is setting you up for directory harvest attack, a complete guid on that is here -> http://www.amset.info/exchange/filter-unknown.asp <- Equally as dangerous is enabling Authenticated Relaying if you don't have a need for it.

Finally, your queues full of rubbish, that could be numerous issues, the most likely is NDR spam - follow this to ensure you are not relaying spam and to clean up the server (I doubt that you are an open relay) -> http://www.amset.info/exchange/spam-cleanup.asp

 

by: limjiananPosted on 2009-08-06 at 02:22:01ID: 25031372

i reckon is a NDR spam.

you can always check your domain is under blacklist via www.mxtoolbox.com

this website will assist you on troubleshooting

 

by: dbarmanPosted on 2009-10-19 at 05:20:50ID: 25604463

bmachtolff::

Setting up a connection filter:  What do I use for the DNS Suffix of Provider value?

20120131-EE-VQP-002

3 Ways to Join

30-Day Free Trial

The Experts

98% positive feedback on 31,087 answers since March 2000. angeliii is a Microsoft Most Valuable Professional for his work with MS SQL Server & Develoment.

He has also proven his knowledge of Visual Basic Programming, PHP Scripting and Oracle Databases.

The Experts

97% positive feedback on 10,752 answers since July 2000. lrmoore has more than 18 years experience in the networking industry.

The six-time Mircosoft MVPs specialties include firewalls, virtual private networking, and network management.

Testimonials

"...and excellent source for support... Kind of like having your very own IT dept." Electriciansnet

Testimonials

"I was apprehensive at signing up at first. However... it has already made my life as an IT administrator much easier." JaCrews

Testimonials

"WOW! You guys have great, active, and knowledgeable people on here." moore50

Business Clients

Business Clients

In the Press

"If you’ve got a question... Experts Exchange can supply an answer.”

In the Press

"...an invaluable aid for both IT professionals and those who require tech support."

In the Press

"where IT professionals provide quick answers on just about any topic"

Business Account Plans

Loading Advertisement...