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Exchange SMTP--how to setup relaying properly

Hi, I cannot figure out how to authenticate properly to my Exchange SMTP relay server. I need to set up SMTP so that users can send mail from their mobile phones using SMTP. I have verified that port 25 is open and also that I can send email when I turn on Anonymous Login. The issue is that I don't want to have an open relay and I want users to authenticate to SMTP from any computer or mobile phone and be able to send. I am using the mailbox of the administrator user.

Assuming my user name is "administrator" and my domain is "domain" and password is "password", when I set up Outlook I cannot send once authentication is required. I've tried:


username: administrator
username: domain\administrator
username: domain/administrator

and i cannot authenticate at all. I know my password is correct as I can correctly authenticate and receive IMAP emails on both iPhone and using Outlook. What can I do next to resolve?
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goldylamont
Asked:
goldylamont
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1 Solution
 
goldylamontAuthor Commented:
Amiruk,

OWA is already configured and functioning properly.

OMA? How will setting up OMA make sending through my SMTP server work? I need to be able for users to access email via IMAP and send via SMTP using clients such as Thunderbird, Outlook as well as on mobile devices. OMA looks like it talks over web ports..something totally different than SMTP.
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Cris HannaCommented:
What kind of mobile phone OS are we talking about?
Iphone
Android
Windows 6.5
Windows Phone 7

No SMTP relay required...Exchange ActiveSync is available for all the above..

If you're talking Blackberry you can use OWA or Blackberry Enterprise Server Express

This question is in the Small Business Server, are you using SBS?? if so, which version?
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goldylamontAuthor Commented:
I am using Windows Server 2003 with Exchange 2003

I want to send email from:

  1)  Blackberry devices -- without using Blackberry Enterprise Server--we cannot install this on our server for various reasons. You mention using OWA on Blackberry devices? Using the Web Browser?

  2) Internal Scanner/Printer -- we have an HP printer on internal LAN that we'd like to scan and send documents via SMTP

  3) Thunderbird, Mac Mail (or Outlook WITHOUT EXCHANGE connection) via SMTP

Everyone is mentioning all these ways to avoid using SMTP but I need SMTP working. Does anyone actually know how to setup SMTP for Exchange?
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Cris HannaCommented:
regarding black berry   http://btsc.webapps.blackberry.com/btsc/search.do?cmd=displayKC&docType=kc&externalId=KB03133

Any reason you can use the free Blackberry Server Express?

As far as the scanner/printer...have you configured it to point to the IP of the Exchange server and on port 25...With Exchange 2003 these typically just work when you configure the scanner/printer to point to the IP

Are these other mail clients (Thunderbird, MacMail, etc) receiving mail from the Exchange server?
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goldylamontAuthor Commented:
Hi, so first I want to thank you for looking at my question. But please understand, i have zero issues receiving mail from the server in any way. I can receive mail via IMAP and Exchange fine. My problem is with SENDING emails. I can send via Exchange fine, but I need to enable sending via SMTP for all the other connections to work.

No, I cannot connect and send via SMTP on default port 25. The problem lies in permissions--no matter what password/user combination I use I can't authenticate correctly. I am using the domain admin user for testing using Outlook Express on the Exchange server to bypass any firewall and it still won't authenticate. The only time I've gotten it to work is when I turn off authentication completely--but I can't do this because then I have an open relay. How do I fix this??????

Thanks for the Blackberry link this may be a good workaround for these users. I still need to figure out SMTP authentication though.
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Cris HannaCommented:
I'm aware that you're not having issues with normal send receive..just trying to understand your environment.

I'm going to start by suggesting that allowing your users to dictate the methods by which they collect their mail is not always the ideal situation.   Exchange was never really intended to act as a POP3 Server but they have attempted to accommodate.

Exchange is configured the way it is to prevent open relay (your server being used by spammers)

But this article should get you where you want to be http://support.microsoft.com/kb/823019
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goldylamontAuthor Commented:
I've requested that this question be deleted for the following reason:

no one can seem to answer my question on how to get SMTP authentication working with Exchange 2003. I'd like to close this question out. I almost closed before but reopened to see if there would be more insight however I haven't gotten a suitable answer. Thanks for the help though. Please close this question.
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Cris HannaCommented:
I have supplied methods for Blackberries to work and I have submitted methods for pop3 customers to send through Exchange...after my post on 6/13 the author never reported that this did not work for him or any error messages resulting from attempting to implement it
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Cris HannaCommented:
I intended to hit the object button instead of submit with my previous comments
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goldylamontAuthor Commented:
CrisHanna while I appreciate you replying, I stated above that I CANNOT install Blackberry Enterprise on this server. It's too risky because the server is too old and client does not want to risk it and we have decided to put any consulting work towards a new system we are migrating to. So, BES is NOT and option. Sorry if this wasn't clear, but I thought I made it clear that I would not and could not use BES.

Also, I mentioned several times that I have zero issues receiving email. Also that the issue seems to be specific to authentication with SMTP. The easiest test I use to test for email on Exchange is to use Outlook Express on the exchange server itself to connect. Doing this I can receive via POP or IMAP, however I cannot AUTHENTICATE to SEND email using the domain admins email account (which works fine for receiving). The only way I can Authenticate and send using above method was to temporarily open my server up as a relay and obviously this isn't the solution. I've isolated issue to be authentication and was just hoping for help with this.

Also wanted to point out that I didn't use all Caps above to be mean! :-D I just want to point out the things that went unnoticed in my previous posts.
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goldylamontAuthor Commented:
whoa, I have been a good and courteous EE user for years. please be easy with the language there. i previously tried to close the question and then was nice enough to reopen it for more dialogue. the responder didn't even read through my responses. I've responded again so (s)he can review what was overlooked. I'll give the commentor a while to respond before requesting closing this.
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Cris HannaCommented:
I've read your responses carefully
I provided a link for using Outlook Web App on your blackberry http://btsc.webapps.blackberry.com/btsc/search.do?cmd=displayKC&docType=kc&externalId=KB03133  after you made it clear that you can't use BES or BES Express

I think you misunderstand the purpose of the second link which is titled How to help secure SMTP client message delivery in Exchange 2003

It walks you through step by step on how to allow Exchange to securly receive mail from pop3 and IMAP clients, but requires setup on both Exchange and the client side.
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goldylamontAuthor Commented:
i just need to close this out and I don't have time to troubleshoot this issue any more. thanks crishanna for your efforts
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