iPhone setup with POP configured on Exchange 2003 running on SBS 2003

I have a Windows SBS 2003 running Exchange that is configured for POP/SMTP.  A remote user just purchased an iPhone (3G) and we cannot get it setup to use POP to download emails from the Exchange server.  We've been on the phone with Apple and AT&T, so far nothing.  This user only uses OWA to access email, she does not use the contacts or calendar in Exchange, so all she wants to get on her phone is email.  Sending email is OK because we used AT&T's SMTP server.

The SBS is not fully up to date but it is running SP2 and Exchange 2003 SP2.  When setting up other POP email clients (i.e. Outlook), I've can use any one of the following syntax for the settings:
POP server: mail.external_domain.com
Username: username@external_domain.com OR username@internal_domain.local OR internal_domain\username

When setting up Windows mobile phones with a POP account and this server, it would only accept this syntax for the username: username@internal_domain.local

I've tried all 3 ways with the iPhone but it either gives an error message that the username and password is incorrect or it actually says it connects to the server but it never downloads any emails.  I know there are emails on the server because she only uses OWA to check email.

I've read through a lot of the questions about iPhone and Exchange setup, but I haven't found an answer that has helped me.  Please help.
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Jian An LimSolutions ArchitectCommented:
I have done once using SBS 2003.

Since all the emails are kept in exchange, you can try to setup using the exchange way.

first, verify http://servername/oma to see whether it works without problem.

IF yes, you can setup the iphone using exchange way (much easier)

please keep me posted if you need more help

hausen4uAuthor Commented:
Are you saying put in http://servername/oma for the POP server on the phone?  Or in a web browser?

I just entered it into my web browser and was asked credentials.  I logged in and received a message saying that the device type is not supported.  I clicked OK and received a text listing of all the folders for that user's mailbox.

I will try it on the phone as the POP server and report the results.
hausen4uAuthor Commented:
So we just tried a couple different combinations (servername/oma, http://servername/oma, https://servername/oma) for the POP server, none of which worked.  Each time it would try to check email the phone would give the message "Failed to connect to server"
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Jian An LimSolutions ArchitectCommented:

I means Try to setup your Iphone through exchange method instead of the traditional POP accoutn

goto settings/Mail/Add account/ Microsoft Exchange

your server name is your <servername> which can access from outside and inside
username: as it
password: as it

This method you don need to worry so much about the POP settings...

of course, try to test it internally before you try to test it externally
hausen4uAuthor Commented:
I do not want to set it up that way because it will be a pain for this user.  This user does not use Exchange to manage her contacts or calendar.  So if we setup the phone to use Exchange, she will have to go through and enter everything into Exchange, which is not an option.

All I want to do is setup the iPhone to work with a POP3 server that is running on Exchange.

Also, she is 100% a remote user, so she is never internal on the network.  Hence the reason that all I want to setup on the iPhone is email using POP.
Jian An LimSolutions ArchitectCommented:
1. have you turn on the services ?
2. have you open the ports and forward it to your server?
recheck the settings on iphone. delete the current one. Then
goto settings/Mail/Add account/others
put in your external exchange server name
put in the email address and password as it speak

please update me
hausen4uAuthor Commented:
As stated in my original post, I have setup both Outlook and other "smart" phones to work with this server using POP/SMTP, all without a problem.  So all the services are running and all the ports are forwarded.

I believe we have already tried deleting and recreating the account on the phone, but I'm not 100% certain, so I will try that and report back.
hausen4uAuthor Commented:
Ok, we deleted and recreated the account.  For POP settings:

Hostname: mail.external_domain.com
Username: username@internal_domain.local

With those settings, the phone first cannot verify the settings, so it asks if it should try without SSL and we select yes (because the email server is not using SSL for POP), and the phone eventually verifies the account.  When going into the Inbox, the status shows Connecting then Updated, but no messages are downloaded.  I also tested sending a new message (thinking maybe it's not downloading old messages), but that didn't work.

So we deleted and recreated the account again, this time using the following for the username:


But that gave the same results.
Jian An LimSolutions ArchitectCommented:
have you tried on something like gmail to see whether it works ?
hausen4uAuthor Commented:
Yes, the user has a Yahoo email account and that works.
Jian An LimSolutions ArchitectCommented:
trust me .. i am running out of idea now ..

the last thing i would do is ..


this is a tools that able to customise your configuration (with right username and password) and able to apply to your ipod ...

hausen4uAuthor Commented:
I will try that config utility tomorrow.

It's got to be something, because the phone can "see" the mail server, it actually connects to it but it never downloads anything.

Any other experts out there have things to try?
hausen4uAuthor Commented:
Using the iPhone Configuration Utility did not work.  It gave the same results as entering the information manually.  I made sure to delete the account we created manually before importing the profile.

Anyone else?

I can't believe I'm the only one that has ever tried to setup the iPhone using POP from an Exchange server.
hausen4uAuthor Commented:
Well, since I didn't get a response from anyone else, I tried setting up IMAP.  I already had IMAP setup on the Exchange and for the particular user.  So I forwarded ports 143 and 993 to my Exchange server.  I went into the Properties for the IMAP virtual server and checked "Require SSL/TLS encryption" and restarted the IMAP service.

I then setup my Outlook client at home to connect using IMAP and SSL.  When I tried to download my messages it gave me a prompt about the certificate (because the certificate we use is self-signed) and I clicked Yes to allow anyway.  Then it started downloading all of my emails.

So I deleted all previous email accounts we setup on the iPhone related to this email address and setup a new account using IMAP and SSL.  When checking the mail, it said it could not connect with SSL, so we tried without.  It connected to the server and started downloading items from all the folders EXCEPT the Inbox.  It downloaded all of her Exchange Contacts, Drafts, Sent Items, and Deleted Items.  But when she goes into the Inbox, she gets the message "Connection to server failed, cannot get mail".

Help, please!!!
hausen4uAuthor Commented:
hausen4uAuthor Commented:
Well Apple Enterprise support and Microsoft support won't even touch this type of setup.  They both say to use Exchange ActiveSync, which doesn't work for this user.

I guess it's a lost cause.....

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