Problem sending mail to user with an external mail server.

Posted on 2006-06-29
Last Modified: 2010-03-06

here is the situation...

I have recently created a new user on the domain. this user uses a laptop and is quite often away. So, we have setup a new mail account for him on external mail server.

Then, the boss asked me, if i could include him in the global contact list. so i have setup a mailbox account for the user and now his name appears in the list. all happy. but when someone tries to send a mail to him, who is within the domain, the mail is never received. Now in the email addresses tab of user properties, the smtp address is clearly pointing to the external mail address. but he never receives those emails. prior to setting up a mail box he was able to receive, but now, he can only receive messages that are sent from outside the exchange server, but not those who use the server.

So, just as trail and error, i deleted his mailbox(using exchange tasks, when u right click). now, when ever they(people usung xchange) try to send, an error pops up, saying there was a problem connecting the two servers or the two recipients, please contact your administrator.

Now, im only a novice in xchange. so, im not sure, if i did something wrong. or right.

Now does the above problem sound familiar, if so, i would really appreciate if someone could help me out. thanks a ton for looking into my problem.
Question by:JustCs
  • 3
  • 3

Expert Comment

ID: 17009697
the only way to relay messages like you want is to use a contact. Exchange assumes that any address that you assign to a user is a local mailbox.
So you will want to remove the user account you created.
What you need to do is create a mail enabled contact inside of active directory. Give this contact the External SMTP address. I assume you are using the default Global address lists for exchange so this new contact should also show up in your address list. Now, when you send mail to this person, exchange knows to send it outside of your organization.


Author Comment

ID: 17009777

yes, i created a new mailbox so that he shows up in the list of those who use xchange server for sending mails.

Now, when you say, that i have to create a mail enabled contact...what exactly should my steps be?...i mean how to proceed and where to start.

Sorry, but as i said, im not good at xchange.

Author Comment

ID: 17009823
Also, not sure if this is related to xchange, but the funny thing is...

his mail account is quite weird. i have setup all the details for him to access outllok, but when i test it, it goes till logging in, but fails to send a test email. it says to check the email address, saying its invalid.

Now, the server acts as a dhcp server, and all the systems are connected thru serever. so does this have any effect when trying to connect to outside mail servers.
PRTG Network Monitor: Intuitive Network Monitoring

Network Monitoring is essential to ensure that computer systems and network devices are running. Use PRTG to monitor LANs, servers, websites, applications and devices, bandwidth, virtual environments, remote systems, IoT, and many more. PRTG is easy to set up & use.

LVL 18

Expert Comment

ID: 17009876
Go to ADUC and go to users right click on users and click contact to create contact with external email address of user.

Accepted Solution

athelu earned 200 total points
ID: 17010493
Log on to the exchange server.

Open up active directory users and computers.
Navigate to the folder(OU) where the users are stored.

Make sure and remove the User Account that you had created to try to do this before. The reason is A) it wasn't working, and B) smtp email address is a unique property of Active directory and two objects cannot have the same address listed.

Now Create the New contact record:

Right click the OU and choose "New", then choose contact.
Fill out the general information for the user, click next.
Make sure that the "Create an exchange e-mail address" box is checked (this is what mail enables it).
set the alias to something unique - such as
Click the modify button next to the Email field.
Choose SMTP Address from the list presented.
put in the users external email address (ie
Say OK, click next, then finish.

Author Comment

ID: 17010699
cheers guys, i'll try it out and let u know.

also, out of curiosity, when i was checking other members' details, who share the same profile as the person, im tryin to setup, they all had the same settings(right like this guy. but their's are working alright.

cant understand y, only this one wont work. now to be honest, i didnt check their mailbox folder(to c if they had one). Now lets say i follow ur process and setup a contact, will i be able to c this guys name just like anybody else's in the active users directory. and if i right click on him, would he b sharing the properties as everybody else.

Expert Comment

ID: 17012304
He will be listed in active directory, his Icon will be that of a contact and not a user.

The Default Global address list should also list him, so if the users opened the address book from inside of outlook his contact record would appear. It will not look any differently in the list - but its properties will be slightly different.

Featured Post

Optimizing Cloud Backup for Low Bandwidth

With cloud storage prices going down a growing number of SMBs start to use it for backup storage. Unfortunately, business data volume rarely fits the average Internet speed. This article provides an overview of main Internet speed challenges and reveals backup best practices.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

This article explains in simple steps how to renew expiring Exchange Server Internal Transport Certificate.
This article aims to explain the working of CircularLogArchiver. This tool was designed to solve the buildup of log file in cases where systems do not support circular logging or where circular logging is not enabled
To add imagery to an HTML email signature, you have two options available to you. You can either add a logo/image by embedding it directly into the signature or hosting it externally and linking to it. The vast majority of email clients display l…
This video shows how to quickly and easily add an email signature for all users on Exchange 2016. The resulting signature is applied on a server level by Exchange Online. The email signature template has been downloaded from: www.mail-signatures…

809 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question