Internet mail problem.... (Full Version)

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ckoster -> Internet mail problem.... (30.Oct.2001 3:06:00 AM)

Hi All,

I'm having a problem recieving internet mail to my server. I'm a newbie at Exchange so this may be a pretty basic question. First off, here is the setup:

Windows 2000 Server running SBS 2000.
Exchange 2000 installed and not writing any errors to the event logs.
IIS is running and not writing any errors to the event log.
Can send internal emails between client machines and server with no problem.
Can telnet port 25 successfully.
Changed my MX record on the external DNS server to point to the external interface of my machine.

The problem is when I send email from outside of my domain (i.e. hotmail or yahoo mail) I get the following message:

Message from
Unable to deliver message to the following address(es).

<test@>: does not like recipient.
Remote host said: 550 5.7.1 Unable to relay for test@
Giving up on

NOTE: I'm using the IP address instead of the domain name in the email addy as I just changed the MX record to point to my box this weekend and I'm not sure if the changes have fully taken effect yet.

Anyone have any ideas on what the problem is? I've seen a few other similar questions in this forum but haven't come across a definate answer yet.

Some ideas I have:

1) I've read about the IMS (Internet Messaging Service?) in some forum messages. I don't see this service running on my machine. Is this necessary to be able to get internet mail?

2) I'm running ISA server on the same box as my SMTP server. I've configured ISA per instructions but Doc Shinder says that you shouldn't run ISA and an SMTP server on the same machine. Could there be a problem with this?

Thanks much for any help you can provide.


jeffj -> RE: Internet mail problem.... (30.Oct.2001 11:14:00 PM)

1. Internet Mail Service is an Exch 5.5 Service, not an e2k Service. No you don't/can't use it.

2. E2k REQUIRES smtp, therefore IIS. If ISA is on the same box, you need to change port numbers for Default Web Site to 81 or something, because ISA will want 80, and other ports.

ckoster -> RE: Internet mail problem.... (31.Oct.2001 3:00:00 AM)

Thanks for the reply, Jeff.

I'm not trying to use IMS as I did figure out that it's a 5.5 feature.

As for IIS/ISA - I have the ISA Inbound Web access listening on port 81 and left all IIS sites at port 80 so I don't have any conflict there.

I've actually muscled the thing so that I can now send mail from the internet to the server without getting any errors but, unfortunately, the mail I'm sending does not go into any mailboxes. Not sure why this is. When I send an email from Hotmail or Yahoo I can see the activity on the LAN lights so I know the message is getting to the box but when I refresh the mailboxes to see if the message made it there's nothing there.

Do you have any ideas why this might be? Right now I have configured two virtual SMTP servers per a Microsoft article I found. One SMTP server listens to the external NIC and relays (or is supposed to, I should say) the mail to the appropriate internal user's mailbox. The other virtual SMTP server is used for outgoing mail (i.e. internal user to internet).

Do I have to set up anything in the recipients area or set up another connector? Right now I only have one SMTP connector and the local bridgehead is pointing at the SMTP virtual server that is configured for outgoing mail.

Any ideas would be much appreciated.



P.S. - Does my problem have anything to do with the POP3 side of things? From what I understand the POP3 virtual server and POP3 protocol is only to provide the functionality for remote users to download the mail out of their Exchange mailbox.

[ October 31, 2001: Message edited by: Craig Koster ]

jeffj -> RE: Internet mail problem.... (31.Oct.2001 3:43:00 AM)

Well, what happens when you Telnet to the IP address of the external nic on the ISA, to port 25? Do you see an esmta Mail Service, i.e., port 25 of e2k box?

Check Default or Whatever Recipient Policy in ESM. Is it the correct smtp domain for you?

Check the Queues under SMTP Virtual Server.

ckoster -> RE: Internet mail problem.... (31.Oct.2001 2:53:00 PM)

I can telnet correctly to port 25 and see the ESMTP service message.

Under the default recipient policy I have the following:

On the General tab there's a Filter Rule that says (mailnickname='). On the email tab I have two Generation Rules: a STMP rule for address and an X400 rule with address c=us;a=;p=CORRECTNETBIOSNAME;o=Exchange.

I don't see anything in any of the queues under either of my SMTP virtual servers.

Should I be using two virtual SMTP servers (i.e. one for inbound and one for outbound) or is this not a good idea? I've read that Exchange is pretty much ready to go out of the box so I was a bit hesitant to screw around and create a new virtual server but I need to get this working ASAP.

I think I'll turn on logging to see what I can find there.

Not sure what else to do about this. Do you have any suggestions for articles or books that will show explicitly what a typical Exchange server setup will look like? I'm looking for examples of how to configure SMTP and POP3 for basic use (nothing fancy in my setup). Any recommendations are much appreciated.

Thanks again for your help.


ckoster -> RE: Internet mail problem.... (31.Oct.2001 3:47:00 PM)

A new note: I just got a bunch of the following messages in my Yahoo mailbox (the mail client I'm testing from):

This is an automatically generated Delivery Status Notification.



Delivery to the following recipients has been delayed.




Attachment: Message/delivery-status

Reporting-MTA: dns;
Received-From-MTA: dns;
Arrival-Date: Tue, 30 Oct 2001 19:44:55 -0600

Final-Recipient: rfc822;administrator@
Action: delayed
Status: 4.4.7
Will-Retry-Until: Thu, 1 Nov 2001 19:44:55 -0600

Does this mean that my messages are making it to the server but Exchange can't resolve the address to an internal mailbox? I looked up the error code (4.4.7) at MS and it seems to say that the message sat in a queue until it expired (I have it set to send delay notification at 12 hours). I don't see any messages in any queues, though. Very weird.


ckoster -> RE: Internet mail problem.... (31.Oct.2001 4:04:00 PM)

OK...yet another update (sheesh this is getting long).

I finally can see messages I send in the queue SmallBusiness SMTP Connector (SMTP Connector - Remote Delivery) that is under the my Default SMTP Virtual Server.

Now, the problem is how do I get those messages from the queue to deliver to the correct mailbox? If I am reading things correctly, Exchange should do some sort of lookup to find the correct mailbox and then route the message. Is this correct?

Thanks. Think I'll run out to B&N to see if I can find any good Exchange books!

LaTshitshia -> RE: Internet mail problem.... (31.Oct.2001 5:29:00 PM)

Hey Craig, what is your DNS setup like. This sound to me like a DNS issue.

ckoster -> RE: Internet mail problem.... (31.Oct.2001 7:29:00 PM)

Originally posted by LaTshitshia:
Hey Craig, what is your DNS setup like. This sound to me like a DNS issue.

I am using an external DNS ('s) for my domain. I have my domain name set up to point to my external NIC IP address (A record). I also have an MX record set up to point to my external NIC with the domain suffix ( Not sure if this would be a problem so I will probably change the MX record to be just to be safe.

Not sure if there's anything I need to do for my internal network DNS in order to help Exchange resolve incoming Internet mail to specific mailboxes.

Any ideas are much appreciated.



LaTshitshia -> RE: Internet mail problem.... (31.Oct.2001 7:41:00 PM)

I had a simillar problem and what I did was point my exchange to our internal DNS and point our internal DNS to forward external DNS request to our ISP DNS servers.
If you wish, you can call me at 845-222-3981.

LaTshitshia -> RE: Internet mail problem.... (2.Nov.2001 10:17:00 PM)

Microsoft article Q229840 might help you.

jafpq -> RE: Internet mail problem.... (3.Nov.2001 7:00:00 AM)


Did you figure out the problem? I am having the exact same issue.

ckoster -> RE: Internet mail problem.... (4.Nov.2001 12:47:00 AM)

Thanks for all the help, folks.

I did get things running correctly, finally.

Unfortunately, I had to rebuild my whole server as I started having major troubles that I couldn't figure out (port conflicts, ISA Server trouble, along with Exchange problems). Once I rebuilt the box, I configured Exchange per a book I got - Mastering Exchange 2000 Server by Barry Gerber. It's a pretty good book for Exchange beginners/novices as it steps you through setup and configuration very nicely.

Once I got everything configured, with the help of the book I figured out that I did not have a correct A record sitting along with my MX record on my external DNS servers. I logged in to and added the correct A record for my server and once the change kicked in I started getting emails like I should.

Hope that helps a little, jafpq. Again, I'd highly recommend that book if you're just starting with Exchange or have limited experience. Cost $50 U.S. but it was well worth it.


P.S. - In my previous posts I mentioned a setup where I had two SMTP Virtual Servers (one incoming and one outgoing). Just a note that this configuration seems unnecessary and I'm not quite sure why the article I got that idea from suggested it.

jafpq -> RE: Internet mail problem.... (5.Nov.2001 4:29:00 AM)

thanks for the info! I was able to get mine to receive finally.....however i'm having trouble receiving from a different domain now.

Thanks again.

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