Exchange Server 2003 with Apple Mail Setup Issues

Hi everyone,
I've been trying my hardest to setup my designer's Mac on our Exchange 2003 Server with Apple Mail with little success. I was able to setup the Exchange account as the Outlook Web Access server is setup for IMAP. However, I seem to have trouble with the incoming and outgoing mail servers. Running through the Connection Doctor says that the account is connected, however the outgoing mail server is not responding. I am using the mail server info from my MIS guy. For examples:
I setup the Outlook Web Access Sever as: "OWA-XX/exchange"
- This seems to connect the account
I setup the Outgoing Mail Server as: "mail-xxx2", with password enabled. This server address was provided to me by my MIS guy
- The Mac claims is cannot access this server.
Any suggestions here? My buddy is running the latest 10.4 on a old PowerMac G4 QuickSilver.

My buddy upgraded to Office 2004 with Entourage which did the trick!

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Exchange Server 2003/2010 Coexistence Mail-flow Issues

I've installed Exchange 2010 in a 2003 coexistence scenario.
2010 was deployed with CAS,HUB, and Mailbox roles.
The installation went through smoothly, and the default RGC was created.
On the 2010 Server, when I create a new users with mailbox, that user is no able to send or receive mail from anywhere.
2010 user to 2010 user does not work
2003 user to 2010 user does not work
Mail delivery between 2003 users works fine.
The RGC message queue in ESM 2003 shows that the messages are queued and keep retrying.
I have deleted the RGC twice and created new ones, I have un-installed the HUB and CAS roles and re-installed them, and I have also re-run setup /preparead and setup /preparelegacyexchangepermissions
I'm not able to make any sense of the message tracking on the 2010 side. It just shows a bunch of entries:
EventID: NOTIFYMAPI
Source: STOREDRIV
When I use the best practices analyzer to test mailflow to a 2010 user from the outside, the test comes back with a pass even though the message itself isn't delivered to the specified mailbox.
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Any ideas?
Here is the mail flow analyzer result:
Testing inbound SMTP mail flow for domain '[email protected]'.
     Inbound SMTP mail flow was verified successfully.
     Additional Details
Elapsed Time: 3437 ms.
     Test Steps
     Attempting to retrieve DNS MX records for domain 'test.com'.
     One or more MX records were successfully retrieved from DNS.
     Additional Details
MX Records Host mail.test.com, Preference 0
, Host test.com, Preference 10
Elapsed Time: 110 ms.
     Testing Mail Exchanger mail.test.com.
     This Mail Exchanger was tested successfully.
     Additional Details
     Test Steps
     Attempting to resolve the host name mail.test.com in DNS.
     The host name resolved successfully.
     Additional Details
     Testing TCP port 25 on host mail.test.com to ensure it's listening and open.
     The port was opened successfully.
     Additional Details
Banner received: 220 EX2K3w2K3.test.net Microsoft ESMTP MAIL Service, Version: 6.0.3790.3959 ready at Wed, 5 Feb 2014 14:40:44 -0500
Elapsed Time: 368 ms.
     Analyzing SMTP Capabilities for server mail.test.com:25
     SMTP Capabilities were analyzed successfuly.
     Additional Details
     Attempting to send a test email message to [email protected] using MX mail.test.com.
     The test email message was delivered successfully.
     Additional Details
Elapsed Time: 621 ms.
     Testing the MX mail.test.com for open relay by trying to relay to user [email protected].
     The Open Relay test passed. This MX isn't an open relay.
     Additional Details
     Testing Mail Exchanger test.com.
     This Mail Exchanger was tested successfully.
     Additional Details
     Test Steps
     Attempting to resolve the host name test.com in DNS.
     The host name resolved successfully.
     Additional Details
     Testing TCP port 25 on host test.com to ensure it's listening and open.
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     Additional Details
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No duplicate security groups. I did notice Exchange 2010 is not in the Exchange Domain Servers group, but 2k3 is. Not sure if that matters.
In the Application event log I'm seeing this error a lot.
Log Name: Application
Source: MSExchangeMailSubmission
Date: 05/02/2014 3:02:31 PM
Event ID: 1009
Task Category: MSExchangeMailSubmission
Level: Error
Keywords: Classic
User: N/A
Computer: ex2010w2k8.test.net
Description:
The Microsoft Exchange Mail Submission service is currently unable to contact any Hub Transport servers in the local Active Directory site. The servers may be too busy to accept new connections at this time.
Event Xml:
<Event xmlns="http://schemas.microsoft.com/win/2004/08/events/event">
<System>
<Provider Name="MSExchangeMailSubmission" />
<EventID Qualifiers="49156">1009</EventID>
<Level>2</Level>
<Task>1</Task>
<Keywords>0x80000000000000</Keywords>
<TimeCreated SystemTime="2014-02-05T20:02:31.000000000Z" />
<EventRecordID>6530</EventRecordID>
<Channel>Application</Channel>
<Computer>ex2010w2k8.test.net</Computer>
<Security />
</System>
<EventData>
<Data>HubTransport</Data>
</EventData>
</Event>
As long as you cannot send email between ex2010 users this has nothing to do with connectors/smtp config..
I had the same issue one year ago and solved adding both sevrers to old/new exchange sevrers security groups.
Looks like for some missing security entry (not sure why) mailbox is unable to conact HUB  (MSExchangeMailSubmission) I expect you seing items stuck in draft for owa (outbok for outlook)
I saw in some blogs similar cases solved by setting static DNS servers for HUB severs config.
Yes that is similar to what I'm experiencing.
When using the Outlook client with a 2010 mailbox the mail leaves the outbox fine. When using OWA new messages just get saved as drafts when I try to send them.
I will try your suggestions. I see two groups. Exchange Domain Servers, and Exchange Enterprise Servers of which Exchange Domain Servers is a member.

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Mail only works on MS Exchange 2007 or later. Please refer to
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My place of employment recently hired a 3rd party company to handle setting up and managing our servers. This includes our email, which is now run on Microsoft Exchange Server 2008.
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Message was edited by: JTelcontar (typo!)

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I have a similar problem here i have work accounts which do not need the SSL ticked but when I uncheck the box and in a few seconds the tick is back up again sometimes I have to click about 10 times or so for it to stay off. I tried to do your sollution it did not work on your suggested port but seemed to work on the 25 port . Also I found i only have the problem when I am at work were we are on a PC network and firewall. It seemed to work fine on a normal home line. Also it only happens on Mountain Lion I have a older macbook with snowleopard and there i have not problems sending messages
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I'm having some issues properly setting up 10.7.3 to host internal DNS and external Web, Wiki and Mail. I'm having issues with the web and wiki hosting. Since those are the most important right now, I haven't really had a chance to fully test the other features. I was able to do some testing of the mail and iCal but it was limited.
Long read below but I thought the specifics would be helpful...
My goals and configuration are:
***GOALS***
Primary:
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2) Host a public wiki: main.example.org and www.main.example.org
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4) Host a public, group calendar
4a) Read only to majority - Read/Write to a group
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Physical:
1) Business class Internet (no blocked ports)
2) A single, public and static IP address
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4) Wildcard Cert: *.example.org from GoDaddy
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DNS Config
10) I used the admin tool to open DNS and change:
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12) In the "Nameservers:" block, I changed the zone name there but left the nameserver name alone (zone: example.org /// Nameserver Hostname: main.example.org).
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OD Config
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SSL
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In order: File Sharing, Mail, AB, iCal, Web, Wiki, Profile Manager, Network Groups, Network Users
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Website:
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Access to the website works on the server but external access doesn't (Network Error/timed out tcp_error). Checked the AirPort settings using the AirPort utility (version 5.5.3) and the Port Mapping (under the "Advanced" icon) show serveral services all pointing to 10.0.1.5. Thinking it could be DNS I tried main.example.org externally and it failed the same way.
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I removed the example.org Machine Record from the zone and it now looks like:
PZ=example.org / ZONE=example.org / NS=main.example.org
Machine Record=main.example.org / IP=10.0.1.5
RM=10.0.1.5 / Resolves=main.example.org
PLEASE HELP!

The amount of users (if relevant):
On site - 1 (Me)
Off site - 16 (Windows clients - some have iOS devices too)
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Incoming email - Routing rules on exchange server 2003

I am configuring SAP system to receive emails as per note 455140. We currently have only one client and have updated necessary profile parameters including setting SMTP port to 25 for incoming mails. We have specified our enterprise exchange server 2003 as the mail server in SCOT transaction and are able to send out emails from SAP without issues, but cannot receive emails in SAP.
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Hello Markus,
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"SAPconnect like most mail platforms route mails via the email address.
SAP recommends the following:-
UserATClient.SID.company.com
I know that a DNS entry will have to be written for this to be routed
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The only other recommendation is to use the local part of the mail
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entry but every new user will have to be updated in Exchange.
User.client.sidATcompany.com
There are no other way of correctly routing mails other than these
methods. Thank you."
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Any suggestions.
Thanks,
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Compatibility Exchange Server 2003 SP2 and Domain controllers Windows Server 2008 R2

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regards
Microsoft Certified IT Professional Server Administrator

Exchange Server 2003 SP2 supports DCs running Windows Server 2008 R2. These DCs should be RWDCs and not RODCs:
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My Website Link
My Linkedin Profile
My MVP Profile

Portal integration with Exchange server 2003 issues.

Hello,
We are using NW04s EP 7.0 SP16 and Exchange server 2003. We are trying to perform OWA and Groupware integration. Both the servers are in the same domain.
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I hope this saves some people the hours of time that it cost me!!

I have managed to get incoming mail to work. It is the outgoing settings that are still not working on my system. I have tried every configuration. I have gone back and forth between Verizon and Apple Care too many times to count.
Do you have to turn down the security level on the FIOS router/firewall before making these changes? If you do, it probably makes the system more vulnerable to malware, etc.
I have standard Yahoo Verizon mail. I believe you can enable it for POP mail. It certainly always worked for me before. Like you I have tried everything. I was also told that my internet connection is PPPoE versus DHCP which may also cause problems. Like you, I have spent days trying to sort this out.

Anybody using MBA OSX able to use "Notes" to Sync with the notes located on a exchange server 2003 pls?

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Hello,
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Hi,
To deploy local Exchange server integrated with Office 365, we can depend on Exchange Server Deployment Assistant:
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Having trouble connecting apple mail to Microsoft exchange server 2003 on this Mac. Currently Entourage is in use (Office 2004) and working. Apple Support and our IT man have tried to solve it together, filling in all relevant fields of the account information. The only questionable field was "Outlook Web Access Server" which we first left blank then filled in later. This should work but does not. Resulting in mail sitting in the outbox while trying to send. Connection Doctor confirms that "Mail was unable to connect to the internet" while both the "Incoming Exchange" and "Mail Server" are trying to connect to the server. Anyone got any clues.
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I feel your pain. I also am a lone Mac user in an entire building full of PC robots, and the IT people haven't got a clue.
I've been trying to get Mac mail working with the Exchange server here, but it's just not happening. I've managed to get Entourage working though, which is far from ideal but significantly better than the web-based version of Outlook that I'd been having to use up till now.
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Best of luck,
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UK

Exchange Server 2003 with Apple Mail Setup Issues

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