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Exchange 2010 will not send email to outlook, email doesnt show up in OWA

Posted on 2010-04-01
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Hi everyone.  I'm fairly new to Exchange and had only messed with it pre-2003 so I'm sure it's probably something I'm missing/doing wrong here.



I swapped my MX records to point to my static IP at the office where the exchange server is sitting so I could test functionality.  My local exchange domain is domain.local and my actual email domain is domain.com.  I've made domain.com the authoritative domain, and set a new default email address rule for domain.com instead of the normal domain.local that would automatically be there.



Now....I have what I think are good send/receive connectors as well.  I have two users set up (I and another user that I knew was a heavy emailer) to test with.  Each user, while the MX records were changed, could send email out without a problem (except to a few domains that didn't have the DNS update yet I'm assuming, for example, the mailbox could send to gmail and have it arrive immediately, but I still haven't received any email in a hotmail account I was using in this test, and my wife's exchange at her office could send/receive to our domain fine).



The mailbox properties for both mailboxes show that, for example, the heavy user has/had (I say had only because we changed the MX back for the time being, however it still technically says they have these items in the mailbox) 9 items in the mailbox at 16KB total.  I'm sure that includes sent email as well, however I only sent 4, so there should have been 5 new email in the mailbox if I'm reading that correctly.



When I connect to OWA or outlook with that user's account, I see nothing in the mailbox however.  So the properties show that there are items there, but the only items I see are the sent items, there's no new outside email showing up (send/receive says it worked fine in outlook with no errors of course).  



I feel like I'm missing something small, but I just don't know what it is exactly, and I'm sure with something like this it's going to vary by instance, so instead of searching the internet over fruitlessly today like I did yesterday, I'm going to hope someone can help point me in the right direction.

I'm not using edge transport by the way, only hub transport.
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Question by:Varalith
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by:Hilal1924
ID: 29339901
The items count in your mailbox is not just email, it could be task, calendar items, Sync Errors, Custom Contacts etc as well. Just to be on the safer side, can you do the following test with SMTPDIAG.

smtpdiag uremailaddress@domain.com urhotmail@hotmail.com /v
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by:Hilal1924
ID: 29339961
Also Forgot to add, Please check the queues, Message Tracking Log also. See where the message went before it was lost or delivered.
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by:Varalith
ID: 29341226
I'm assuming the SMTPDIAG is a command to be ran on the exchange server?  And will it matter if the MX records have been changed back for the time being, or will it still trace properly?

Also, I'm not positive on how to check the queues or the log.  I went into the toolbox yesterday to try, and it kept forwarding me to some KB article on ex2007 where the steps didn't apply to 2010.
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by:Hilal1924
ID: 29341699
It should work as long as your email address is allowed to send mail through your server.

for Tracking logs take a look at this:

http://exchangepedia.com/blog/2009/06/user-self-service-message-tracking-from.html

and This:
http://briandesmond.com/blog/exposing-organization-level-message-tracking-in-exchange-2010-owa/

You need to add yourself to the security group called "Message Tracking". Via Role Based Access Control wizard either through EMC or via PowerShell.

Cheers,
Hilal
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by:Varalith
ID: 29342152
Alright thanks, I'll play with that in a few.  And at the moment email is not set to flow through our server anymore....it's being re-routed through our service provider's servers as of this morning again (had it done so we wouldn't be completely down while I tried to figure this out).

According to the message queue, I don't have messages in there for what it's worth.
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by:Varalith
ID: 29367132
Ok, new information since I last posted....a user that didn't have a mailbox on the new server received an email while our old server was down and the new server was up.

This email of course was kicked back, but the error message that was with it said this:

The message could not be delivered because the recipient's destination email system is unkown or invalid.  Please check the address and try again, or contact your system administrator to verify connectivity to the email system of the recipient.

Now...knowing this, I started thinking about something.  The MX record was changed to our public IP by the hosting company (yes, they shouldn't be changing it for me, but we have something strange going on here that was setup long before I got here).   They changed it to the following:

xxx.xxx.xxx.xxx.domain.com

If we didn't have an A record to go along with the mail server yet (to correlate mail.domain.com to xxx.xxx.xxx.xxx (where x is the ip address)), and really regardless of whether or not the A record existed...should they not have just put the IP address?  There's really no reason to put our domain.com in line and directly after the IP....then it goes from being an IP to a FQDN if I'm not mistaken, which would mean the DNS wouldn't know how to route it.  Which would then explain why I could send mail but not receive it (if the server was actually receiving the email, it would have been visible in OWA even if outlook couldn't pull it down).

After all.....the IP is where the server resides, and the IP is x....it's not x.domain.com.
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by:Hilal1924
ID: 29367623
You are right, The MX record should point to your Spam Filter which recieves mail from external world. I believe your firewall is already set up to deliver port 25 traffic to your Spm Gateway. From Spam Gateway it will be delivered to your mail Server.
btw to set up an MX record on your hosting company, They will need a Public IP, Domain/Server Name. First they have to create an A record and then they will create the MX record. A record is a pre-requisite for creating MX Record.
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by:Varalith
ID: 29367626
Also, for what it's worth.....all the email I thought I received yesterday was just hanging around apparently....this morning it all went to the right place even though some of it was delayed by several hours from the time the MX record was changed at 7 CST to now (I got something a few minutes ago, around 1:15pmCST, that was sent out at 11:57amCST yesterday).

That makes me think, if what you said is correct about the items and the size of the items, being calendar items, etc.  I did sign into outlook on both exchange accounts while I was testing, and the computers I signed into outlook on had .pst files opened in outlook.  I wonder if the calendar items and such from those logins merged into the exchange mailbox.  

Even more strange was the fact that my wife sent me an email to my address which I didn't add as a mailbox on the exchange server until an hour later  (initially I just wanted to see if it would bounce, which I don't think it ever did because her DNS was routing it to the old server at the time), and I got the email this morning at my address on the old mail server, but when I made my exchange mailbox for my address, I never checked how many items I had.  Then after signing in on outlook and seeing no items, I went and checked the mailbox and it said I had 1 (I don't get a lot of email so I figured it was probably the one my wife sent).  I wonder if that's the case now, or if I merged an object into that mailbox by signing in on outlook with a profile that had a .pst with a calendar object on it already.
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Author Comment

by:Varalith
ID: 29367702
Ok so the A record should read mail.domain.com......and the MX should be my IP, correct?

If that's all that's wrong I'll just have them fix it first thing next week an we'll try it again.
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by:Varalith
ID: 29367809
Also, I don't have a spam filter yet since I"m just testing.......the host had a baracuda at their site, and I'll be purchasing one once I know this server is going to work.  At the moment port 25 and 110 are forwarding directly to the server's IP from the public static IP (which should be the MX record).
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Hilal1924 earned 2000 total points
ID: 29368066
Great, Give it a try and let's keep our fingers crossed :)
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Author Comment

by:Varalith
ID: 29914275
Ok, so changing those MX records to something that could resolve properly worked.  The problem I have now is, I realized the other day that I had screwed up my SSL certificate (as far as the domains, both locally and externally, etc.) and needed to make some changes.  

I had one re-issued, but since I updated the certificate this morning, I can't send from exchange anymore.  

Any ideas there?
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