Configuring Exchange Mail

I am a small business owner with limited IT knowledge.  I have installed SBS 2008 on my server and wanted to use the Exchange functionality that in budnled with it.  I presently can receive mail and send to most locations.  I do however have three issues: 1) there are some site that I can't send mail to, Exchange sends me a Deliver Delay message and never is able to send the message, 2) utilizing Outlook on the server, it is constantly asking me for a login password that it can never resolve, 3) I am unable to get Active Sync to work with my HTC phone.  Below are the specifics: (i am using representative names and IP's)

GoDaddy  
Domain name      GDdomainname.com
A Record - @ 99.99.999.99
                   remote 66.666.666.666  (I got this IP from my linksys router under the admin tab)
MX    10   @    remote.GDdomainname.com
Service    _autodiscover   _TCP   @   443    remote.GDdomainname.com

Server
Computer name - MainServer.AAA.local
domain   AAA.local

Additionally, I can get into web access using the http://remote.GDdomainname.com.  It seems to behave in the same manner however.  I also purchased and installed a SSL from GoDaddy  issued to remote.GDdomainname and a gd-iis-intermidates which i also installed (hopefully both were done correctly but I can't be sure.

I know this is a long winded message but I truly am pulling my hair out and thus far none of the typical resoures have been of much help.  Any guidance will be greatly appreciated.
haallcAsked:
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Rob WilliamsCommented:
A couple of reasons your e-mail may not be being delivered is:
-if sending from a public IP
-if you have not set up a reverse DNS record with your ISP
-both of the above should be avoided if you set up SBS with the default of using a smart host (routing e-mail through your ISP)

As for continually prompting for a password;
There is a recent ‘known issue” where Outlook 2007 will constantly prompt for a user name and password after some recent server updates have been applied, if running Exchange 2007 (SBS 2008). These are updates that are approved automatically if you have WSUS enabled on SBS, or you may have manually installed. It is believed this is due some recent changes to authentication methods made by Microsoft.
Microsoft’s solution is to apply any of the following updates, which require manual WSUS approval to resolve the problem:
Exchange rollup 9 (or 8)
http://www.microsoft.com/downloads/details.aspx?FamilyID=55320be2-c65c-48bb-bab8-6335aa7d008c&displaylang=en
Exchange SP2
There are issues installing SP2 on SBS 2008. To eliminate, or minimize these first run the “Microsoft Exchange Server 2007 SP2 Installation Tool for Windows SBS 2008” from:
http://www.microsoft.com/downloads/details.aspx?displaylang=en&FamilyID=ffd2fe61-9278-489e-9b96-3816394c9cb6
Then install SP2:
http://www.microsoft.com/downloads/details.aspx?FamilyID=4C4BD2A3-5E50-42B0-8BBB-2CC9AFE3216A&displaylang=en
Additional reading:
http://blogs.technet.com/sbs/archive/2010/01/14/exchange-server-2007-service-pack-2-installation-tool-for-sbs-2008-released.aspx
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haallcAuthor Commented:
Thanks for the guidance - the answer on the password was excellent.  I could use some clarification on whethter I have GoDaddy configured correctly and how I would check to see if the certifactes are installed and in the correct store.  Sorry I was more concise in my orginial email.
Regarding your response on the sending issue;  public IP - the two IP are GoDaddy and the IP of my cable modem,  reverse DNS lookup with the ISP, going to need help with that one, and how would I check the smart hosting - i dont believe im using it but could be wrong on that one.  Again thanks for the quick and helpful response.
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Rob WilliamsCommented:
To check your GoDaddy cert install, from off-site try connecting to RWW or OWA:  https://remote.yourdomain.abc  or https://remote.yourdomain.abc/owa  If you don't get a certificate error you probably have it properly installed.
For detailed information see:
http://blogs.technet.com/sbs/archive/2009/12/14/how-to-manually-install-certificates-in-sbs-2008.aspx

Reverse DNS is a record that points your IP to your domain name, effectively the reverse of your remote.GDdomainname.com name. You cannot control this like you can MX and DNS records it has to be done by your ISP.
You can verify your DNS and MX records and more with a couple of test sites:
http://www.mxtoolbox.com
https://www.testexchangeconnectivity.com/Default.aspx

You can see if you chose to use a smarthost by going to: Windows SBS console | network Connectivity | bottom of the list, it will show if configured. You don't have to use a smart host but in most cases it eliminates the "best practices" rule of needing a static IP and Reverse DNS record.

If in doubt about your SBS run the best practices wizard which will catch all sorts of configuration issues, if any, and suggest repair options:
http://www.microsoft.com/downloads/details.aspx?familyid=86a1aa32-9814-484e-bd43-3e42aec7f731&displaylang=en
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haallcAuthor Commented:
I'll run the test and post the results.  I am hopeful this will help me get this going.  I'm also thinking that Smart Host may be the way to go.  Would I have to make any changes at GoDaddy to use this function?  One other thing, if I may, the configuration I have set at GoDaddy, does it look correct?  I have had various opinions over the last few days and no longer sure if it is correct or if optimum.
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Rob WilliamsCommented:
>>"Would I have to make any changes at GoDaddy to use this function? "
No

>>"configuration I have set at GoDaddy, does it look correct?"
I am not certain exactly what you have there. I found it a little confusing.
The 2 important items you need are:
1) a host (A) record that points  remote.yourdomain.abc  to your public IP (the WAN/Internet IP of the router)
2) An MX record that points mail fro your domain to your host record  remote.yourdomain.abc and set with the highest priority 5 or 10 depending on the service/company
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haallcAuthor Commented:
Thank you Rob your sharing your expertise.  I will try the tests that you suggested and post the results to insure I am interrupting them correctly.  You have been a big help, more so than any of the other aveneues I have tried to date
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Rob WilliamsCommented:
Thanks haallc. I hope it helps to get the final "tweaks" resolved. Let us know how you make out.
--Rob
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haallcAuthor Commented:
As an update - I installed smart host and unfortunately my ISP- Comcast- doesnt support a static IP with my present service, also they use port 587.  I have ordered an upgrade to a business class service and that should open up the ports that I need to make this work.  I still am unable to send from mydomainname.com.  
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Rob WilliamsCommented:
There are ways to use a dynamic IP and different ports with paid subscriptions to dyndns.com or no-ip.com, or are you OK waiting for the ISP account upgrade?
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haallcAuthor Commented:
I already have an free account with dyndns.com.  Honestly, I am getting close to wits end.  Every thing I try seems to lead to another issue.  I ordered the upgrade and it will be installed late next week.  The problem now is that after installing the smart host and using the IP assigned to my cable modem, I still cant send email through the exchange server.
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Rob WilliamsCommented:
Can you send internally?
There is very little to configure with exchange when sending mail. If you can't send using the smart host, it is likely the ISP blocking the traffic. They often do that on non-commercial accounts. You can remove the smarthost but some domains will not accept mail from a dynamic IP or without a reverse DNS set up.
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haallcAuthor Commented:
I believe it to be the ISP - when I talked with them they felt this upgrade would solve my problems.  Let's hope so.  I really appreciate your help Rob and sticking with it.  I can send as long as I use the ISP account so I'm OK for the short term.
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Rob WilliamsCommented:
OK. I'll "hang in" and let us know how you make out.
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haallcAuthor Commented:
I am waiting for my ISP to install new equipment aand new service that should open up the ports necessary to make this work.  I would like to leave this open until I can get that installation accomplished and see what other, if any, issues I may run into.
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Rob WilliamsCommented:
No problem. Let us know when they have completed the changes.
You may need to re-run the networking wizards once they have done so.
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haallcAuthor Commented:
I apologize for not updating you on my progress.  Unfortunately, several things have happened and I have been unable to focus on this issue.  I will update this forum when I can get back to task.  Thanks again for all your help along the way.
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Rob WilliamsCommented:
I believe the initial question was properly answered but the smart host issue at the end was an ISP issue and needs to be worked out by client with their service provider.
--Rob
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haallcAuthor Commented:
Due to a hectic travel schedule, I was unable to complete the ISP portion of the solution, but that doesnt have anything to do with the advice (which was excellent) that Rob provided.  Thank you
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Rob WilliamsCommented:
Thanks haallc.
Cheers!
--Rob
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