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Problem sending email from Windows XP email client to Exchange server Outlook client

Posted on 2008-06-20
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Last Modified: 2010-03-06
1. I have networked 2 computers: Windows XP and SBS 2003 running exchange server

2. The computers can send email back and forth through outlook, i have done the following

a Setup Exchange server
b. Create administrator account with admin-email account in AD;
c. Setup outlook on xp machine;
d. Create profile that attaches to Exchange;
e. Login to Exchange server with this admin account;
f. Send email to XP machine from server to workstation and vice versa.

3. However i need to send a message from a generic email client from the XP machine to the exchange
Note: i can send an email from the exchange to the generic email client on the xp machine but it cannot reply

Question: are there any restriction on the exchange that is not allowing incoming emails from the XP client?

Any advise would be extremely appreciated!

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Question by:kgballa
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by:dextermain
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How is your exchange setup.

Is it setup to allow users on the server to send, but does not act as a relay host of the from email address is not know on the server. Eg you can allow IP range to send mail via the server.

What is the error message you get when you reply.

Please post the error message.This will help to solve the problem.
If possible see if you get errors on the exchange server's logs.

Good Luck
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by:kgballa
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All i've done is create an email account in AD, The outlook clients from the XP and SBS communicate, and when i try to reply from the XP machine's generic email client i get the "Delivery to the following recipients failed" and in the C:\WINDOWS\system32\drivers\etc\  directory i have configured the "hosts" file to look for my XP machine with the appropriate IP
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by:dextermain
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Hi kgballa

Please provide the full error.
Do you use MS Outlook or Office Outlook?
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by:kgballa
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Error from the generic email client on Windows XP is:

"This is an automatically generated Delivery Status Notification.

Delivery to the following recipients failed.

       Administrator@contoso.com"

Im using Microsoft Office Outlook 2003 on both machines. They can both send and receive emails from each other. And the Outlook on the exchange can send an email to the generic email client on the xp machine, however the email client on the xp machine cannot reply. Thanks
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by:dextermain
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Hi,

Do you use the Ip address of the exchange server as SMTP server?
Please make sure that the message you reply to have the correct email address.
Deactivate your antivirus scan outgoing email.

Try that and let me know what you get.
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Author Comment

by:kgballa
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no i use a domain name contoso.com. No antivirus or firewall installed or enabled. when the generic client recieves the message from outlook it attaches a .6 at the end of it for example Administrator@contoso.com.6 and when i receive that email i reply and thats when i receive  that delivery failure error
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by:dextermain
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Hi,

Try using the ip address of the exchange server as outgoing mailserver just for a test and see what happens!
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by:kgballa
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This is a stupid question and im sorry but where do i implement that?
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by:dextermain
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Hi,

In outlook se tools - email account - edit - and set you SMTP server to the IP.

Please let me know the outcome.

;)
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by:kgballa
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I tried the suggestion with no success. The outlook clients communicate with each other just fine sending and receiving back and forth(both outlook clients are setup for exchange). Do think this can be an issue with the poilcy on the exchange server? or the email/user settings?
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by:dextermain
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Hi,

Have you tried it on another PC.

If the email clients settings is correct.Then it is a setting on the server.
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Author Comment

by:kgballa
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I just want to say that i appreciate you help, i feel like ive gone through everything i know on the exchange do you have anysuggestions?
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Accepted Solution

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dextermain earned 500 total points
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Hi

Sorry no more suggestions on my side. It must be some kind of setting.

Take a look at this link. It might help.
http://www.webagesolutions.com/training/microsoft/2011/outline.html

Try a reboot of the PC and server. ( It's Windows )

Good Luck. Let me know if you have any more information.

;)
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