Question

Exchange server smtp error 500 5.3.3 Unrecognized command

Asked by: d3m00n

Hi,

I have a problem with commonication between two Exchange servers 2003.

exAsrv-FWsiteA----VPN------FWsiteB----exBsrv

Where:
exAsrv - Exchange 2003
exBsrv - Exchange 2003
FWsiteA - Cisco ASA5505 ver 7.2(2)
FWsiteB - Cisco ASA5505 ver 7.2(2)

Problem is when I try to comunicate with both servers on port 25.

1.
a)From exAsrv.mydomain.local I can telnet to port 25 to exBsrv.mydomain.local, but I see:
220 ****************************************************************************
*****************************************
helo
500 5.3.3 Unrecognized command

b)From exBsrv.mydomain.local I can telnet to port 25 to exAsrv.mydomain.local, but I see:
220 ****************************************************************************
*****************************************
helo
500 5.3.3 Unrecognized command

From RFC I have only information which I don't understand, why command line to long???
      4.2.1.  REPLY CODES BY FUNCTION GROUPS

         500 Syntax error, command unrecognized
            [This may include errors such as command line too long]

2. Another test. I enabled possibilyty on both exchange servers to comunicate on port 252:
a) From exAsrv I can telnet to port 252 to exBsrv, but I see:
220 exBsrv.mydomain.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.3959
ready at  Fri, 8 Feb 2008 14:43:58 +0100
helo
250 exBsrv.mydomain.local Hello [192.168.1.200]

b)From exBsrv I can telnet to port 252 to exAsrv, but I see:
220 exAsrv.mydomain.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830
ready at  Fri, 8 Feb 2008 14:45:07 +0100
helo
250 exAsrv.mydomain.local Hello [192.168.0.17]

On the site B exchange server is available from outside as a main server, however I want to
set up replication of both server. But now it is not a problem.

I checked configuration on both cisco routers:
1. NAT rules are setup correctly.
2. I disabled ESMTP inspecion on both sides.

Trraffic seems like is going correctly.

3.
a) Test telnet from host1B.mydomain.local(winXP) to exAsrv.mydomain.local to port 25.
220 ****************************************************************************
*****************************************
helo
250 exAsrv.mydomain.local Hello [192.168.0.23]

b) Test telnet from host2B.mydomain.local(GNU/Linux) to exAsrv.mydomain.local to port 25.

Connected to 192.168.1.200 (192.168.1.200).
Escape character is '^]'.
220 *********************************************************************************************************************
helo
250 exAsrv.mydomain.local Hello [192.168.0.5]

c) Test telnet from host2B.mydomain.local(GNU/Linux) to exAsrv.mydomain.local to port 252

Connected to 192.168.1.200 (192.168.1.200).
Escape character is '^]'.
220 exAsrv.mydomain.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830 ready at  Fri, 8 Feb 2008 15:17:04 +0100
helo
250 exAsrv.mydomain.local Hello [192.168.0.5]

d) Test telnet from host3B.mydomain.local(WinXP x64) to exAsrv.mydomain.local to port 25.
220 ****************************************************************************
*****************************************
helo
500 5.3.3 Unrecognized command
e) Test telnet from host3B.mydomain.local(WinXP x64) to exAsrv.mydomain.local to port 252.
220 exAsrv.mydomain.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.1830
ready at  Fri, 8 Feb 2008 14:45:07 +0100
helo
250 exAsrv.mydomain.local Hello [192.168.0.32]


Does one of you see any regularity as I don't.

Where can be a problem?

I think that somwhere in Windows, but don't see any regularity.
Please note I tested it when software FW are disabled on both sites.

Thank's for any suggestion.


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

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. VPN tunnel into Cisco ASA via static NAT from router???
    I have a client with a Layered Cisco network solution. Their Cisco router is public facing and provides a private IP address to the Cisco ASA behind it. I need to be able to create a VPN tunnel into the ASA. There are public IP addresses available to be statically NAT'ed t...
  2. Cisco PIX  VPN and NAT
    Hi, I need to have a VPN from a PIX506e and a remote private network We will use NAT to map certains through the VPN 192.168.100.0/24----PIX506----internet----------------------remote FW------Private lan 172.16.1.0 we want to NAT 192.168.100.10 to be seen as 10.10.10.10 fro...
  3. Cisco 2600 Router VPN and NAT Config
    I have a VPN tunnel confined with a remote site. The Main site has a Cisco 2611 Route and two windows server. I have NAT rules opening ports 3389, 80, 143, 110 and 25 to the outside world to the servers. The problem I'm having is the remote site is not able to access the port...
  4. FW Setup with PPPoE
    Hi Experts. I am setting up a NetGear fw to work with a DSL router. I have setup the PPPoE settings on the fw but still cannot get the internet to work once I make the changes in the wiring closet. I noticed on the DSL router that there are several options regarding the PP...
  5. NAT-VPN problems
    Hello, I have some problems with NAT - VPN and I hope that someone have a solution. The scenario is: There is single Cisco 1800 Series router that is used. Users need RDP access both via VPN and without VPN. This means first option is connect to VPN than access the Termina...
  6. Cisco router 87x - Combining NAT & VPNs
    Hi, We have Cisco 87x routers and 2 sites lets call them siteA and siteB. There is a Cisco VPN tunnel between siteA and siteB setup using the SDM Wizard. The problem we have is if we create any incoming NAT rules like the following - At SiteA incoming NAT rule for SMTP to ...

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

 

Expert Comment

by: FC01Posted on 2008-02-08 at 06:30:14ID: 20850343

Comments are available to members only. Sign up or Log in to view these comments.

 

Expert Comment

by: d3m00nPosted on 2008-02-08 at 06:39:02ID: 20850454

Comments are available to members only. Sign up or Log in to view these comments.

 

Expert Comment

by: d3m00nPosted on 2008-02-08 at 06:43:31ID: 20850525

Comments are available to members only. Sign up or Log in to view these comments.

 

Expert Comment

by: FC01Posted on 2008-02-08 at 06:51:17ID: 20850630

Comments are available to members only. Sign up or Log in to view these comments.

 

Expert Comment

by: d3m00nPosted on 2008-02-08 at 06:56:36ID: 20850692

Comments are available to members only. Sign up or Log in to view these comments.

 

Expert Comment

by: d3m00nPosted on 2008-02-08 at 06:59:27ID: 20850738

Comments are available to members only. Sign up or Log in to view these comments.

 

Expert Comment

by: FC01Posted on 2008-02-08 at 07:06:09ID: 20850817

Comments are available to members only. Sign up or Log in to view these comments.

 

Expert Comment

by: d3m00nPosted on 2008-02-08 at 07:13:17ID: 20850888

Comments are available to members only. Sign up or Log in to view these comments.

 

Expert Comment

by: FC01Posted on 2008-02-08 at 07:25:28ID: 20851035

Comments are available to members only. Sign up or Log in to view these comments.

 

Expert Comment

by: d3m00nPosted on 2008-02-08 at 07:26:13ID: 20851050

Comments are available to members only. Sign up or Log in to view these comments.

 

Expert Comment

by: d3m00nPosted on 2008-02-08 at 07:40:43ID: 20851205

Comments are available to members only. Sign up or Log in to view these comments.

 

Expert Comment

by: d3m00nPosted on 2008-02-08 at 07:50:10ID: 20851284

Comments are available to members only. Sign up or Log in to view these comments.

 

Expert Comment

by: FC01Posted on 2008-02-08 at 08:35:45ID: 20851696

Comments are available to members only. Sign up or Log in to view these comments.

 

Expert Comment

by: d3m00nPosted on 2008-02-08 at 09:00:32ID: 20851957

Comments are available to members only. Sign up or Log in to view these comments.

 

Assisted Solution

by: FC01Posted on 2008-02-08 at 09:08:09ID: 20852021

Comments are available to members only. Sign up or Log in to view these comments.

 

Expert Comment

by: d3m00nPosted on 2008-02-08 at 09:08:42ID: 20852032

Comments are available to members only. Sign up or Log in to view these comments.

 

Accepted Solution

by: d3m00nPosted on 2008-02-12 at 08:18:24ID: 20876150

Comments are available to members only. Sign up or Log in to view these comments.

20120131-EE-VQP-001

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...