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Send Email to Internal Exchange on Wireless Access Point

Posted on 2013-11-08
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Last Modified: 2013-11-18
I have an internal SBS 2011 domain configured with Exchange 2010.  I am setting up a wireless access point that is on the same subnet as my internal network mostly for our iPhone's.  Everything seems to work great and I even have internet access when connected to the access point.  The issue I am having is sending email from my Exchange account on the iPhone.  On my iPhone I have my domain exchange account configured and pointing to my public exchange server address, mail.domain.com, for example.  But when trying to send email on this access point it does not work.  My guess would be that since this access point is internal and the Exchange email account on my phone is pointing to the public address it simply does not know how to route email to my internal exchange server.  

How would I allow any wireless device on this access point to send exchange email to my internal mail server?  I'm not sure if this could be a DNS issue, or if the access point simply doesn't know how to route this properly and needs to somehow be pointed to my internal domain exchange server.  

Any information is appreciated.
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Question by:ColumbiaMarketing
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by:RaithZ
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You should start with the basics, can you ping your mail.domain.com address from a laptop/iPhone on the access point?  Does the name resolve to the external IP address?
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by:ColumbiaMarketing
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Yes, I can ping mail.domain.com from the access point, but it resolves to it's internal private address.
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by:ColumbiaMarketing
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I can also receive mail while connected to the access point, but can not send.
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by:RaithZ
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Is the exchange mail server listening for connections on that internal IP as well as the external IP?  

I believe if you changed the internal DNS to have it point to the external IP address it should work, but I don't know if that would break something else for you.
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by:RaithZ
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Ahh.. then the internal DNS shouldn't need to be changed.  Do you have wired mail clients that can send and receive mail without issue on that same subnet?
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by:lpadmin1
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I have achieved this on my network by creating a DNS record for my email server.  The traffic isn't going to route by going out and then coming back in so you need to pretty much have it so that while the phone is on your network it sends the email directly to your exchange server.  Example, my exchange server's FQDN is exchange20xx.mydomain.com and my external server settings on my phone looks like mail.mydomain.com so what you do is create the dns record for mail to be the IP address of the exchange20xx.mydomain.com
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by:ColumbiaMarketing
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Ok, so my FQDN on my exchange server is exchange20xx.office.mydomain.com and the external address is simply office.mydomain.com, which is the same setting I am using on my phone.  Would I need to create an alias or host record in my internal DNS and would it need to point to my external or internal exchange IP address?
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by:ColumbiaMarketing
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Would this method work if the wireless subnet is separate from my LAN subnet? That is how I currently have it set up and the wireless clients DNS points to my ISP and not my internal DNS server. Would there be a away around this?
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by:RaithZ
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If mail is being received, but not sent that would indicate that traffic is routing just fine... at least to me it does.  Putting it on a separate subnet shouldn't make any difference if that is the case.

Are you using exchange as the account type on the tablet, or is it using pop3/imap and SMTP?

If the later, what do you have as the SMTP server name and does that address resolve to an ip on your internal network?
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by:ColumbiaMarketing
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I apologize for the confusion.  Currently I am not able to send or receive email from my Exchange server while on the wireless.  For a moment I thought I could receive, but I was wrong.

Exchange is the account type on my iPhone.

The Exchange SMTP server on my iPhone points to my public address at office.mydomain.com, which of course points to a public IP.  

It seems that it is having issues looking out to the internet and coming back in for my Exchange email while on the wireless.
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by:RaithZ
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You can verify that by changing the exchange server address to the internal address of your exchange server.  If that works, then that is indeed your problem.  

If that is your problem, you could possibly create an internal DNS entry for your mail server that has the same name as your external one.. if your using internal DNS servers while on the wireless.  Not sure if you are or not.
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by:ColumbiaMarketing
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That definitely seems to be my problem then.  Unfortunately I am not using any internal DNS servers on my wireless router so adding an internal DNS entry won't help in this matter I don't think.  Basically my wireless was set up to have no internal access what so ever as it's strictly for guests.  

The only work around I can think of is to put in another wireless router that does specifically have internal access and can reach my DNS server, then maybe I could then create an internal DNS entry that would point to my local Exchange server IP.
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RaithZ earned 300 total points
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Another option would be to use an external proxy when accessing the internet.  There are a few out there usable or you can setup your own if you have the resources.

The problem is specifically limitations on the router.  It can't do the re-writing necessary to route the packet to the external address located on the internal network.
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