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Remote server did not respond to a connection attempt - SMTP Send issues

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  • Remote server did not respond to a connection attempt - SMTP Send issues

    Ok, first things first, I'll apologize as I'm sure most of what I am inquiring about has been asked too many times and probably answered too many times.

    I began setting up my Exchange Server 2003 about 3 weeks ago, and have made significant progress on every level. I am not usually one to ask for solutions. I usually find the answers by reading and working through a solution. The particular issue I'm experiencing is the only thing preventing my from going live with the server. I've been scouring the net, various message boards/forums, Technet, and numerous other sources for info, and cannot seem to find out why this is happening.

    I installed Exchange 2003 partially because I want to host my own email for my domains (one to start with and possibly another down the road...) and just to learn.

    I know this is old technology... Exchange Server 2003 that is, and that everyone has moved on to Exchange 2007/2010 but this will do the job plus, it's free with part of a MS subscription I've purchased along with several other MS subscriptions/products I own as an OEM/Tech Partner, Certification, etc. As well, moving to Exchange 2007, which I also have, would mean installing a new x64 server(s) which I don't have the time to do at the moment though it is in the plans and I figured that getting this up and running (inspired by working with hosted services for several clients) would be a good learning exercise before I move on to Server 2008 and Exchange 20xx.

    I guess first, the ONLY issue I am having at the moment is certain email getting stuck in queues. That's it!!

    Here's a detailed breakdown of my configuration;

    - DC/GC running on a dedicated computer running Server 2003 x32 (AMD x64 w/4GB RAM, Several data HDDs)
    - Exchange Server 2003 running on a dedicated computer running Server 2003 x32 (Intel P4 Dual Core w/4GB RAM, 2 HDDs)
    - Domain Controller running DNS, DHCP, WINS and a few other biz related items. Very little running on it and it has been a DC and File Server for a couple years
    - Both systems have all Window/Microsoft Updates fully updated
    - Exchange Server has all service packs and patches installed thus Exchange is fully up to date.
    - Exchange is configured as a backend as per several articles on Petri, MSExchange.org, and Amset.info

    I have everything working so to speak. OWA works entirely in every way. I've edited the logon.asp as per an article at MSExchange.org pertaining to login with Username only instead Domain\User, along with one thing I figured out on my own whereby the login page request is for Email and Password rather than Domain\User.

    User Accounts, and Exchange portions of user accounts are configured so I can login via email address and password, just a domain username and password or I can still use Domain\User and password either via OWA or Outlook 2003/3007.

    I have RPC/HTTPS functioning exactly as several articles explain and OWA/RPC is running SSL with my own certificate. For anyone having trouble with RPC/HTTPS, getting the certificate right to match up to the rest of your configurations/settings is THE KEY to getting RPC/HTTPS working. It really is simpler that it comes across.

    I have OMA functioning fully as well as Active Sync, and Direct Push functions. I did all tests with emulators first (Windows Mobile 5 and 6), then setup my HTC Wizard and everything is bang on. This was all done, as per again, several articles on Petri, MSExchange.org, Amset.info, and Microshaft.

    I've setup one SMTP Connector as per Amset.info SMTP Connector article.

    This was done so I could test outbound to one of my Hotmail accounts.


    My MX records are setup with my domain registrar as per the Amset.info DNSConfig article.

    As well, I referred to several other articles on MX Records, SPF and PTR...

    I am using the following convention for my SPF;
    v=spf1 mx mx:mxmail.testdomain.com ~all with mxmail.testdomain.com being replaced with my real info of course.


    I am running on a persistent IP ISP... so not Dynamic like DSL but yet not static... therefore I will retain an IP address nearly indefinitely. In fact, since I've been with this provider (nearly 5 years) I have not seen the IP dynamically change. The only real way to get my IP to change is to power off the cable modem, then program a new MAC Address into my router, save the settings, reboot, the power off the router. Then powering on the modem, and powering on the router will get me a new IP. That again will remain for days, weeks, even months unless I do the above. That said, for all intents and purposes it is a dynamic IP.

    I am running DynDNS with an updater and have configured Split DNS as per the article at Amset.info on Split-DNS

    ...and it works flawlessly just like described.


    All tests worked as they should.

    I can Telnet to my own server, test it, and send messages within Telnet as per the Telnet tests at various sites

    I can Telnet to my ISP's mail servers.

    I can Telnet to most other mail servers but there is the odd one I cannot connect to. My assumption at this point is that those servers simply will not accept a Telnet session being that I can connect to others most likely ruling out an issue on my part.

    I've tested with Microsoft's Exchange Troubleshooting Assistant and Best Practices Analyzer.

    Also tested with the online Exchange Connectivity Test

    ...and both inbound and outbound tests were without error.


    I've also tested with the site MXToolBox

    The only error I get with MX Toolbox and the local Microsoft Tools on the Exchange Server is a reverse DNS error with the local MS tools and a reverse DNS not matching the SMTP Banner with MXToolbox. Further analysis leads me to the conclusion that while most test resolve both ways, the Banner error is because while the Exchange mail server name resolves properly to the IP, the reverse lookup on the IP resolves to the ISPs unique "machine name" assigned to my IP/Connection... a "Super Cookie" so to speak as per Gibson Research's Shield's Up

    I've tested OMA, OWA, Outlook, and Mobile both inside and outside my network and have no problems connecting, receiving and sending except as noted.

    To summarize, I can send email to any of my Hotmail addresses (the SMTP connector relaying thru my ISP's SMTP handles this), I can send email to my ISP email addresses. These move through the Default SMTP Virtual Server. It seems like anything else I send to any other email whether it's one of my GMail addresses, or other people at other ISPs or organizations either hosting their own Exchange or on hosted Exchange, it goes into the queues and doesn't move. I get the typical "Delayed Delivery" notifications but eventually, I will get a faiure message.

    The more I read, the more it is seems to be pointing to the fact that I am on a residential/dynamic connection that may be the reason I cannot send. I cannot get a business connection in my area (I've inquired) and I refuse to pay more money to the ISP for a fixed IP which will likely be on a residential segment anyway... even though the connection is super fast and rock solid, the bottom line is the ISP is a douche bag monopoly and I WILL NOT give them any more money than I have to. Calling them to have them set a PTR is likely not doable.

    Is my solution to run entirely through the SMTP Connector or am I doing something here that is the cause and I'm just missing it?

    If anyone needs more info/detail, I'll be happy to provide it.


    P.S. While I'm here, I have 2 client computers running Outlook 2003 w/BCM.

    To my understanding, the latest updates to BCM/Outlook 2003 will allow BCM to run on an Exchange Outlook profile. I have these Outlook clients running, and connecting to my Exchange while running BCM and there are no issues. The question I cannot find the definitive answer to is, will BCM actually connect to/through the Exchange Server and sync the BCM and allow access from OWA or when Microsoft and other sites say it will run, are they simply referring to not having to run two different profiles as when BCM v1. first came out?

    Also, with Exchange Server 2003 OWA, is it possible to have 15 minute/quarter hour intervals in the calendar as in Outlook or am I stuck with half our/30 minute blocks in the OWA Calendar?

    Thanks to anyone/everyone who read this long winded post.
    Last edited by FireClef; 17th June 2010, 17:40.

  • #2
    Re: Remote server did not respond to a connection attempt - SMTP Send issues

    First - I would drop the SPF records.
    If you are testing then those can do more harm than good. Furthermore they do nothing to stop the amount of spam that you receive.

    Next - the fact that you are not on a static IP address and cannot get a reverse DNS record configured means that you are on a dynamic IP address as far as the rest of the Internet is concerned. IP addresses come in two flavours only - dynamic and static. Yours is dynamic. That means you must send your email through another host to ensure that email is delivered reliably. Some sites will accept your email, some will not. Some will accept it now, then change later. You have no way of knowing.

    The sites that are refusing the telnet test are almost certainly doing a lookup and rejecting connections from your IP address zone.

    Therefore change the SMTP connector to route email through your ISPs SMTP server and you should find email flows correctly.

    If SMTP email delivery was not your question, then you need to state it, because I got bored half way through your question text.

    Simon.
    --
    Simon Butler
    Exchange MVP

    Blog: http://blog.sembee.co.uk/
    More Exchange Content: http://exchange.sembee.info/
    Exchange Resources List: http://exbpa.com/
    In the UK? Hire me: http://www.sembee.co.uk/

    Sembee is a registered trademark, used here with permission.

    Comment


    • #3
      Re: Remote server did not respond to a connection attempt - SMTP Send issues

      Hi Simon,

      Thanks very much for the reply!

      You pretty much confirmed what I was thinking after ALL the testing, configuration, reading... reading... reading..., etc.

      I know for sure that if I open up the SMTP connector everything flows... already tested it! I was hoping to not use this method but it will work quite adequately for now until I decide to pay for a basic mail hosting/static IP or MX routing solution.

      I thought that just maybe something was not just right somewhere but everything else pointed me back to the dynamic IP issue. Even everything about the DNS/rDNS works/worked except for the one PTR issue back to the ISP which I have no control over... and I had a strong feeling that was the problem.

      Btw... I cannot THANK YOU enough for your website Amset... I used it extensively throughout the process of getting everything running. Very helpful, informative, and interesting.

      Much appreciated. Now I can and will move forward and go live with my Exchange.

      Cheers!


      Originally posted by Sembee View Post
      First - I would drop the SPF records.
      If you are testing then those can do more harm than good. Furthermore they do nothing to stop the amount of spam that you receive.

      Next - the fact that you are not on a static IP address and cannot get a reverse DNS record configured means that you are on a dynamic IP address as far as the rest of the Internet is concerned. IP addresses come in two flavours only - dynamic and static. Yours is dynamic. That means you must send your email through another host to ensure that email is delivered reliably. Some sites will accept your email, some will not. Some will accept it now, then change later. You have no way of knowing.

      The sites that are refusing the telnet test are almost certainly doing a lookup and rejecting connections from your IP address zone.

      Therefore change the SMTP connector to route email through your ISPs SMTP server and you should find email flows correctly.

      If SMTP email delivery was not your question, then you need to state it, because I got bored half way through your question text.

      Simon.

      Comment

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