Question

Enabling IMAP on exchange server 2003

Asked by: pir8matt

Hey there. I currently run exchange server 2003, and a couple of my bosses have gotten themselves iPhones. The iPhones ostensibly can use exchange if IMAP is enabled. I've enabled it, and the iPhones can download the messages and folder structure, but they can't send email using it.

This is where it gets hazy for me. Is IMAP actually a sending protocol? Or do I also need to enable POP3? I tested my server with Outlook Express, and OE cant send messages with my server configuration either.

I've already made sure I have the appropriate ports open on my firewall, and I can telnet into the server remotely and make an SMTP connection, which I assume is what is being used to send messages. I just dont understand why its not working. Whenever I try to send a message in OE, I get a 550 error that the recepient was rejected. On the iPhone I get a message that the server doesnt support authentication.

What am I missing here?

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Asked On
2007-07-05 at 04:35:11ID22676538
Tags

exchange

,

imap

,

server

,

2003

,

enabling

Topics

Simple Mail Transfer Protocol (SMTP)

,

Exchange Email Server

,

Email Servers

Participating Experts
2
Points
125
Comments
9

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Answers

 

by: redseatechnologiesPosted on 2007-07-05 at 04:46:48ID: 19423208

IMAP still needs you to send with SMTP, which means you will need to authenticate on the SMTP server (it should be an option on the iPhone, and definitely is in OE) - you do not need to enable POP3.

-red

 

by: pir8mattPosted on 2007-07-05 at 04:51:42ID: 19423225

Ok, so we've established that it will send using SMTP. However, it still doesnt work. I can't send messages. I've enabled explicitly that my account should be able to authenticate remotely in the exchange system manager, but it still won't let me send remotely (using outlook express).

Its not a basic settings problem. I've selected 'my server requires authentication' and Im using the same credentials that Im using to download messages, which is working. Im sure its a configuration issue on the exchange server, but I dont know what Im missing.

 

by: redseatechnologiesPosted on 2007-07-05 at 04:55:55ID: 19423243

Here is Sembee's guide on how to configure (or rather, secure) an SMTP Relay server;

http://www.amset.info/exchange/smtp-relaysecure.asp

That should give you the steps you need to do this properly.

-red

 

by: pir8mattPosted on 2007-07-05 at 04:58:39ID: 19423254

I'll take a look at that. Its worth mentioning at this point that if I send to local addresses, it works fine. It only fails if I try to send to an external host (yahoo, gmail) - so it appears the main problem is that its treating any mail I try to send as local.

I'll read the link and report back.

 

by: pir8mattPosted on 2007-07-05 at 05:01:20ID: 19423267

Yeah, I looked at the link. I've already done this. My account explicitly has submit and relay permissions. If it doesnt work for a single user, its not going to work for a security group either.

I just think its odd that it can send to local accounts, but not remote accounts.

 

by: redseatechnologiesPosted on 2007-07-05 at 05:11:11ID: 19423307

Sending locally is a sign that authenticated relaying is the problem.

It thinks you are relaying - by default, anyone can send to local accounts, so there is nothing strange there.

I would create a brand new account called test123, with the email address of test123

Then try and authenticate (using outlook express or something).

The only other thing I am thinking of off the top of my head is the authentication settings on the SMTP server - open Exchange System Manager, Drill down to your server, protocols, smtp, right click on the default smtp server, properties, and now look for the authentication settings (i am tired, and can;t remember off the top of my head).

In there, you want to have Anonymous and Basic ticked.

-red

 

by: pir8mattPosted on 2007-07-05 at 05:29:06ID: 19423407

"In there, you want to have Anonymous and Basic ticked"

Yeah, they are both selected. I just dont understand why its not going ahead and relaying the message. My account is set up explicitly to allow relay, and even the security group that Im a member of is as well.

 

by: SembeePosted on 2007-07-05 at 12:53:36ID: 19426791

I haven't seen an iPhone, but does it have somewhere specific to set the account for outbound email? If so, what format are you using for username in the account settings?

Simon.

 

by: pir8mattPosted on 2007-07-10 at 10:01:49ID: 19455631

It has your basic SMTP fields for mailserver, username and password.

I'm thinking that the real problem is that my exchange server simply won't relay for anything. I tried smarthosting a webserver through that same exchange server and it won't allow relay either, and it should, because its explicitly allowed to relay for that IP address.

So I think this is actually an exchange issue regarding relay. I'll split these points among everyone who was good enough to answer, and ask a new question about relay not working.

Thanks,

Matt

20120131-EE-VQP-002

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