Can't connect Entourage 2004 to Small Business Server SBS 2008

[dradunsky]

Version: 2004
Operating System: Mac OS X 10.4 (Tiger)
Processor: Intel
Email Client: Exchange

I am supporting a mixed network of Macs and Exchange. We just upgaded to SBS 2008.

I am now not able to connect any of my Entourage 2004 clients. I am able to connect Entourage 2008.

I have:

Installed the Server's certificate in both System and Login keychains.

Since the Mac did not recognize the GoDaddy root. I installed that as well.

I have tried:

<https://mail.client.com/owa> (the original working version for Ex 2007)

<https://mail.client.com>

<Https://mail.client.com/exchange/[email protected]>

Only the last appears to connect at all. However, it just repeatedly asks for the password and doesn't connect.

I have spent at least 2 hours searching the web for a solution. The only item extant is using the last format for the Exchange Server address.

Any assistance would be appreciated.

David Radunsky
(e-mail address removed)

 

[dradunsky]

Sorr forgot to mention that:

We are using localdomain.local as the Domain and username as the username.

All users can log on through OWA and RPC over HTTP with Outlook 2k3.

Thanks.

 

[William Smith [MVP]]

I am supporting a mixed network of Macs and Exchange. We just upgaded
to SBS 2008.

I am now not able to connect any of my Entourage 2004 clients. I am
able to connect Entourage 2008.

Are you trying to use regular authentication or Kerberos?

Have you verified your DNS information for the server is correct and
that the Macs and ping it by name and IP address?

Can you connect using the server's IP address?

If you say that Entourage 2008 can connect but not 2004 then that leads
me to believe you're possibly using Entourage for Exchange Web Services.
Correct? Entourage 2004 cannot use EWS but must use WebDAV. Is that
protocol installed on your server?

--

bill

Entourage Help Page <http://entourage.mvps.org/>
Entourage Help Blog <http://blog.entourage.mvps.org/>
YouTalk <http://nine.pairlist.net/mailman/listinfo/youtalk>
Twitter: follow <http://twitter.com/meck>

 

[David]

William,

Sorry, I have been unable to reply by email to your post and it took 24
hours each time to get noticed that the messages didn't make it.

Please see the embedded answers below:

Are you trying to use regular authentication or Kerberos?

Regular Authentication

Have you verified your DNS information for the server is correct and
that the Macs and ping it by name and IP address?

DNS is working properly. These machines are located outside the network and
worked fine with the 2003/Exchange 2007 server that was replaced with the
SBS2008 (downsizing even happens to networks).

OWA works.

Can you connect using the server's IP address?

Same repeated request for authentication.

If you say that Entourage 2008 can connect but not 2004 then that leads
me to believe you're possibly using Entourage for Exchange Web Services.
Correct? Entourage 2004 cannot use EWS but must use WebDAV. Is that
protocol installed on your server?

No we are just using boring old 2008 12.2.1. I have not yet installed EWS.
Both are using WebDAV.

2008 connects using the following config:
Name: anything
email address: (e-mail address removed)
account: user
domain: domain.local
password: duh
Exchange server: https://mail.domain.com/exchange/[email protected]
This DAV service requires a secure connection is checked

Thanks.

 

[Barry Wainwright]

Hi,

Can you access the server using OWA (Outlook Web Access) in a web browser?

If so, copy the address you use in your web browser to connect and paste
it into the server address field in the account settings.

On the SBS setups I have used, the address has always been something like:
https://server.domain.com/exchange/username


--
Barry Wainwright
Microsoft MVP

David wrote:
William,

Sorry, I have been unable to reply by email to your post and it took 24
hours each time to get noticed that the messages didn't make it.

Please see the embedded answers below:

Are you trying to use regular authentication or Kerberos?

Regular Authentication

Have you verified your DNS information for the server is correct and
that the Macs and ping it by name and IP address?

DNS is working properly. These machines are located outside the network and
worked fine with the 2003/Exchange 2007 server that was replaced with the
SBS2008 (downsizing even happens to networks).

OWA works.

Can you connect using the server's IP address?

Same repeated request for authentication.

If you say that Entourage 2008 can connect but not 2004 then that leads
me to believe you're possibly using Entourage for Exchange Web Services.
Correct? Entourage 2004 cannot use EWS but must use WebDAV. Is that
protocol installed on your server?

No we are just using boring old 2008 12.2.1. I have not yet installed EWS.
Both are using WebDAV.

2008 connects using the following config:
Name: anything
email address: (e-mail address removed)
account: user
domain: domain.local
password: duh
Exchange server: https://mail.domain.com/exchange/[email protected]
This DAV service requires a secure connection is checked

Thanks.

 

[David]

Barry,

Thank you for taking the time to respond.

I believe that I have already answered your question in the original posts
and the followup to the last post.

Status:
OWA, Outlook RPC over HTTP and Entourage 2008 via WebDAV are all WORKING.

the Entourage 2008 Exchange Server string is:
Https://mail.domain.com/exchange/[email protected]

Only thing that does work is Entourage 2004. It does not work using the
above string nor:
http://mail.domain.com/owa (which worked fine with Entourage 2004
connecting to Exchange 2007 on Server 2003.

Thanks.

Hi,

Can you access the server using OWA (Outlook Web Access) in a web browser?

If so, copy the address you use in your web browser to connect and paste
it into the server address field in the account settings.

On the SBS setups I have used, the address has always been something like:
https://server.domain.com/exchange/username


--
Barry Wainwright
Microsoft MVP

David wrote:
William,

Sorry, I have been unable to reply by email to your post and it took 24
hours each time to get noticed that the messages didn't make it.

Please see the embedded answers below:

(e-mail address removed) wrote:

I am supporting a mixed network of Macs and Exchange. We just upgaded
to SBS 2008.

I am now not able to connect any of my Entourage 2004 clients. I am
able to connect Entourage 2008.
Are you trying to use regular authentication or Kerberos?

Regular Authentication

Have you verified your DNS information for the server is correct and
that the Macs and ping it by name and IP address?

DNS is working properly. These machines are located outside the network and
worked fine with the 2003/Exchange 2007 server that was replaced with the
SBS2008 (downsizing even happens to networks).

OWA works.

Can you connect using the server's IP address?

Same repeated request for authentication.

If you say that Entourage 2008 can connect but not 2004 then that leads
me to believe you're possibly using Entourage for Exchange Web Services.
Correct? Entourage 2004 cannot use EWS but must use WebDAV. Is that
protocol installed on your server?

No we are just using boring old 2008 12.2.1. I have not yet installed EWS.
Both are using WebDAV.

2008 connects using the following config:
Name: anything
email address: (e-mail address removed)
account: user
domain: domain.local
password: duh
Exchange server: https://mail.domain.com/exchange/[email protected]
This DAV service requires a secure connection is checked

Thanks.

 

[William Smith [MVP]]

Only thing that does work is Entourage 2004. It does not work using the
above string nor:
http://mail.domain.com/owa (which worked fine with Entourage 2004
connecting to Exchange 2007 on Server 2003.

Very strange. The same settings for Entourage 2004 should work for 2008
without any alteration (except for the Exchange Server string, which is
correct). Have you tried using just the Exchange Server address by itself?

--

bill

Entourage Help Page <http://entourage.mvps.org/>
Entourage Help Blog <http://blog.entourage.mvps.org/>
YouTalk <http://nine.pairlist.net/mailman/listinfo/youtalk>
Twitter: follow <http://twitter.com/meck>

 

[David]

Thanks, Bill.

Yes we have tried:
https://mail.docmain.com
https://mail.domain.com/owa
https://mail.domain.com/exchange
https://mail.domain.com/exchange/[email protected]

Only the last produces results. Those results are a repeated request to
authorize.

I removed the old self signed certificate for mail.domian.com from Keychain
Access. The new certificate is a GoDaddy certificate, which the Mac didn't
seem to want to trust so I installed the GoDaddy root cert as well. Both
certs are installed in the login and system keychains.

OWA works with no warning about certificates

Thanks again for the help.

 

[Barry Wainwright]

Try:

mail.docmain.com

on its own.

 

[David]

Barry,

Hmm. Not sure that I tried that, but what the heck. I'll have to get a
remote to one of the 2k4 machines and try it.

I'll report back.

David