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trying to get mail to flow outside of domain

Posted on 2012-08-13
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Last Modified: 2012-08-13
Hey all me again....yeah, lol. I have my lab built running Exchange 2010, but I want to test mail flow to the internet, mail flows well internally. I have a gmail account that I want to test to, but I am not hitting it. I know I do not have a public MX record since my domain if fictitious. I remember when I was in training for Exchange Migration, I was able to email my gmail with my fictitious domain, it just went to spam. I am assuming that my ISP maybe the reason why I am unable to pass emails thru. So here is my question, what workaround can I implement to test my emails? My ISP is Verizon and I am running FIOS. Is there some kind of public smarthost I can use?
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Question by:xzay1967
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Expert Comment

by:Alan Hardisty
ID: 38287709
Can you telnet to another server outside of your domain on port 25 from your test Exchange 2010 server?

Have you checked that your firewall isn't blocking port 25 outbound from your Exchange Server's internal IP Address?

Are you connected via a fixed IP Address or a Dynamic IP Address as the latter will almost guarantee your mail won't arrive.

Are you sending mail via your ISP's smarthost or direct via DNS?
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Author Comment

by:xzay1967
ID: 38287771
Well this is a VM environment, but of course since it's at my house, my public IP is dynamic. I do have a dynamic updater running via dyn.com if that helps. I did not check the firewall because I was under the understanding that when installing exchange 2010, it automatically configures the firewall rules to open port 25 to allow mail to flow. I will double check to make sure. I will try connecting via telnet to see if I can. Back to the IP issue, my having a dynamic IP should not really matter when it comes to sending mail should it? I am not concerned with receiving emails, just sending, as I don't expect them to come in successfully since my domain is not real.
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Expert Comment

by:Alan Hardisty
ID: 38287945
Try pinging me a test email to alan @ it-eye.co.uk to at least see if your email leaves the building and tries to send to my server.

Then at least you will know if you have a problem via your ISP or just because you are on a Dynamic IP.

Let me know if/when you have sent a test.

Alan
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Author Comment

by:xzay1967
ID: 38288029
Thanks Alan, I sent the test. It should come from ahodo@domain.com. I configured my hub transport to use external DNS servers. I used Googles public servers, 8.8.8.8, 8.8.4.4.
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Author Comment

by:xzay1967
ID: 38288127
Oh, it is not a real user, and the domain is fictitious, it exists only in VM environment. However, I understand what and why you did that, thanks.
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Expert Comment

by:Alan Hardisty
ID: 38288299
Well - if you sent one - it doesn't seem to have found it's way to my server yet!  So it looks like it isn't making it out of your network.

Please try to telnet to my server from a command prompt (once you have installed telnet):

telnet 188.220.xxx.xxx 25

(We always try to protect the innocent - even though it sounds like you don't need it protecting ;) )

Alan
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Author Comment

by:xzay1967
ID: 38288606
I turned off the firewall just to make sure, yet I am still unable to reach you, not even via telnet. I get the could not open connection to the host on port 25 error.
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Expert Comment

by:Alan Hardisty
ID: 38288627
Well - as you are on a Dynamic IP Address, your ISP may be blocking the port (most do) as a security measure, so you should call them and ask them to unblock it as you need it open, or they may say no in which case you could use a different port outbound which they are not blocking e.g., port 26 or 587, but then you would have to use your ISP's mail server as a smarthost.
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Author Comment

by:xzay1967
ID: 38288683
I will try that and see what they say. I was wondering if I could use a service like dyndns as a smarthost service. I think they charge less than 10 bucks a yr for that. If you have any other workarounds please let me know. Was really hoping there was a open smarthost or relay out there somewhere like they have open dns.
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Expert Comment

by:Alan Hardisty
ID: 38288708
It is possible - but only if the port is open - or the port they use isn't blocked by your ISP!

No smarthost will work unless the port they accept mail on is open and that is controlled by your ISP.

Port 587 shouldn't be blocked.

Try telnet to my server again on port 587

telnet 188.220.xxx.xxx 587

You should be able to connect.
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Author Comment

by:xzay1967
ID: 38288926
Well I tried on that port and it failed as well. Knowing Verizon, they maybe using that as well, I know some ISPs use it here as an alternative for SSL on email accounts for their clients. I have seen Yahoo use it, so it would not surprise me if Verizon uses it as well.
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Author Comment

by:xzay1967
ID: 38289189
I was able to telnet to my ISP's mail server. I will configure my exchange to use it as a smarthost and see how that works, will follow up with results.
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Accepted Solution

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Alan Hardisty earned 2000 total points
ID: 38289436
Looks like they are encouraging (read forcing) you to use their SMTP server (smarthost), so if that works, you have to change Exchange to use a Smarthost instead of DNS as you have suggested, which doesn't come as a big surprise.

Did you call them and ask for the port to be unblocked or are you only playing and will move the server to a different IP later on?
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Author Comment

by:xzay1967
ID: 38289497
I got it to work. I added my ISP's mail server to the properties of the send connector. Mail is flowing to my gmail just fine. Thanks again for helping me out.
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Expert Comment

by:Alan Hardisty
ID: 38289505
Excellent - got there eventually - no thanks to your ISP!
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