Entourage not connecting with Exchange Server

J

Janice Pickwell

Hi I hope someone can point me in the right direction:

My Entourage 2004 tells me that I don't have the correct Root Certificate to
connect to the Exchange Server...

I have neither a Signing Certificate nor an Encryption Certificate. Do I
need one and if so where does one obtain said cert.

At least that is what it was saying a few days ago.

I have since tried to return to POP IMAP and have not been able to get
either of those working... Now I get different authentication and
connectivity error messages.....

Everyone else in the office are happily working away on their PC's and I
have been unable to get my Mac to connect to this *&^%Exchange Server.

Do I need to find out if the service provider has the Dav whatever
installed?

I've mangled my Contact Import into Outlook on my PC at home too, but that's
a different issue... One thing at a time.

Thanks, in advance.

Janice
 
N

Nathan Herring [MSFT]

Hi I hope someone can point me in the right direction:

My Entourage 2004 tells me that I don't have the correct Root Certificate to
connect to the Exchange Server...

I have neither a Signing Certificate nor an Encryption Certificate. Do I
need one and if so where does one obtain said cert.

At least that is what it was saying a few days ago.

I have since tried to return to POP IMAP and have not been able to get
either of those working... Now I get different authentication and
connectivity error messages.....

Everyone else in the office are happily working away on their PC's and I
have been unable to get my Mac to connect to this *&^%Exchange Server.

Do I need to find out if the service provider has the Dav whatever
installed?

I've mangled my Contact Import into Outlook on my PC at home too, but that's
a different issue... One thing at a time.

Thanks, in advance.

Janice

Is your account set up to use SSL? ("This DAV service requires a secure
connection (SSL)") If so, then the certificate the Exchange server is using
to secure communication between server and client is the Root Certificate
that Entourage is talking about. Does your Exchange server use a self-signed
certificate or an uncommon certificate authority (CA)? In either case you
will need to acquire the root certificate and import it into you X509Anchors
keychain.

Once you get the certificate, if you're running Tiger, you can just double
click on it (a .cer file in the Finder) and the Keychain app will ask you to
import it onto a keychain, and you can select the X509Anchors keychain.
Alternatively, no matter what OS you are running, you can run the Microsoft
Cert Manager (in the Office "bin" directory), and it will let you import it.

Acquiring the certificate in the first place is another matter. If you try
to browse to your OWA URL via https, does your browser complain that the
certificate is invalid? If so, and it lets you view the certificate chain,
you might be able to extract the certificate. Tiger's certificate viewing
code (which some apps use) let you drag around certificates using their
biggish icons. (So does Jaguar, but it doesn't get the whole cert, but
merely creates a not-so-useful text clipping.)

Hope this helps!

-nh
 
B

Bill Bryson

Nathan,

We are experiencing this problem as well. The error message is that "the
CORRECT Root Certificate" is not installed. Can you explain a bit more
about how Entourage and SSL work to access delegated accounts? This error
message only appears if the user has a delegate account connection
established (e.g. the user has one or more shared calendars). I've
confirmed that these delegated accounts unlike the user's own data are being
accessed by Entourage through the backend server (where the mailboxes
reside) and not through our frontend server (as I assume it should?).

My specific questions are:

1) Since Entourage seems to be bypassing the frontend server and going
directly to the server with the mailbox, in order for SSL to be used I
assume that the backend server must at minimum be configured to respond to
SSL (port 443). Does it also have to have a certificate in order for
communication over SSL to proceed? If there were no certificate, then there
would be no response at all, correct?

2) If SSL AND a certificate must be present on the server, what is this talk
about "the correct root certificate"? Does that mean the server has a
certificate but not the correct one? If so, what might be some reasons it
is "not correct"?

3) I have used a web browser to go to the backend server using SSL (https:)
and we have a Equifax certificate for it. After being prompted for my
UserID and password, I can see the OWA public folder. If the browser has no
problem with the certificate on the server, why would/does Entourage?

4) If our server has a certificate from a known public authority such as
Equifax then there should be no need to install a copy of that certificate
on the client machine?

I'm afraid the implementation of trying to get Entourage to work with
Exchange has been most frustrating.

Here seem to be some basic steps that I believe that MUST be in place to
make the process work:

1) The DNS must provide the exchange server's domain in the list of search
domains. I discovered this from one university's web pages where they were
illustrating the need to do this on the client machines because evidently
like our university the exchange server's domain is NOT being reported from
the DNS. In simple lingo, this means the user must open System Preferences,
click on Network, get to the TCP/IP settings pane, and type in the exchange
server's domain in the "Search domains" text box and save those changes.

Without this, the Entourage setup wizard will never work in its
interrogation to determine the Exchange server settings. This is due to the
strange practice of Entourage using partially qualified IP names when it
interacts with the network. Thus it inquires who is "bill" rather than who
is "bill.domain"?

2) It should be documented clearly (so end users could have a chance to
manually configured Entourage) that the Directory server uses port 3268 for
communication with an Exchange server (click on the advanced pop-down
button). This is NOT the default port associated with most LDAP queries. I
spun my wheels for quite a bit because part 1 was failing and I did not see
any documentation on Microsoft's Exchange/Entourage web pages that brought
out this simple and critical point. This seems to be the default setting
with Exchange.

3) The delegation need for SSL and a certificate on possibly a DIFFERENT
server from the frontend server needs to be highlighted. We wasted a lot of
time and resources trying to track that down and we still have this
certificate warning problem remaining.

I recommend that Microsoft develop at minimum a simple troubleshooting web
page that at least provides a little direction to help speed up the process
of implementing Entourage. There would be less head banging and one step
forward, two steps back. They might start with the above points and include
others such as to be certain that the email field in the Entourage settings
is in the form of "userid@domain" and not "emailalias@domain"


Bill
 
N

Nathan Herring [MSFT]

Nathan,

We are experiencing this problem as well. The error message is that "the
CORRECT Root Certificate" is not installed. Can you explain a bit more
about how Entourage and SSL work to access delegated accounts? This error
message only appears if the user has a delegate account connection
established (e.g. the user has one or more shared calendars). I've
confirmed that these delegated accounts unlike the user's own data are being
accessed by Entourage through the backend server (where the mailboxes
reside) and not through our frontend server (as I assume it should?).

My specific questions are:

1) Since Entourage seems to be bypassing the frontend server and going
directly to the server with the mailbox, in order for SSL to be used I
assume that the backend server must at minimum be configured to respond to
SSL (port 443). Does it also have to have a certificate in order for
communication over SSL to proceed? If there were no certificate, then there
would be no response at all, correct?

Hmm... the delegation scenario is a bit beyond my ken; I will have to ask
around. Any server supporting SSL will have to have an SSL port (default is
port 443) and a certificate. If the backend server does not use the same CA
as the front end server, you may end up having to install the other CA's
root certificate.
2) If SSL AND a certificate must be present on the server, what is this talk
about "the correct root certificate"? Does that mean the server has a
certificate but not the correct one? If so, what might be some reasons it
is "not correct"?

After some inspection, this seems to be an overly generic error string
representing of one of the following problems:
* SSL Handshake failed (though we should have reported why rather than this
generic error)
* Server doesn't support a compatible version of SSL
* Received an incorrectly formatted SSL record
* Received an SSL record with a bad MAC
* Some decrypted data does not appear reasonable
* Server refused renegotiation
* a close_notify alert has been received
* the SSL server requires a client certificate and we were unable to provide
one
* The server's certificate could not be verified.

Obviously, the error message is not relevant to many of these cases, nor is
it sufficiently specific in the last case, where it might be relevant. I
will bring this up with our User Assistance folks to see if we can get it
addressed in a later release.

Unless the server requires client side certificates, I am guessing that the
most likely scenario is an unverifiable server certificate, whether that be
due to it being self-signed and not in the X509Anchors keychain, or whether
it's using a different CA which isn't in the X509Anchors keychain, or
whether we cannot download the intermediate certificates to validate them
against a trusted root certificate. (I'm not sure whether SSL presents just
the server certificate or the whole certificate chain, or whether that's
configurable.)
3) I have used a web browser to go to the backend server using SSL (https:)
and we have a Equifax certificate for it. After being prompted for my
UserID and password, I can see the OWA public folder. If the browser has no
problem with the certificate on the server, why would/does Entourage?

If the web browser is using the OS X certificate store, then Entourage
should have no such problem (and I am not saying that it won't; just that it
should not). IE 5.2.3 has its own legacy certificate store, but Safari uses
the Keychain-based one. I don't know about other browsers.
4) If our server has a certificate from a known public authority such as
Equifax then there should be no need to install a copy of that certificate
on the client machine?

If the particular Equifax root cert is in the X509Anchors keychain in a
default install of the OS, then no. Apple does change what certs to include,
so this might be different depending on what version of the OS.
I'm afraid the implementation of trying to get Entourage to work with
Exchange has been most frustrating.

Here seem to be some basic steps that I believe that MUST be in place to
make the process work:

1) The DNS must provide the exchange server's domain in the list of search
domains. I discovered this from one university's web pages where they were
illustrating the need to do this on the client machines because evidently
like our university the exchange server's domain is NOT being reported from
the DNS. In simple lingo, this means the user must open System Preferences,
click on Network, get to the TCP/IP settings pane, and type in the exchange
server's domain in the "Search domains" text box and save those changes.

Without this, the Entourage setup wizard will never work in its
interrogation to determine the Exchange server settings. This is due to the
strange practice of Entourage using partially qualified IP names when it
interacts with the network. Thus it inquires who is "bill" rather than who
is "bill.domain"?

I haven't tested this out. Do PQDNs not work at all in Office applications?
(e.g., hyperlinks) Or is it this specific case?
2) It should be documented clearly (so end users could have a chance to
manually configured Entourage) that the Directory server uses port 3268 for
communication with an Exchange server (click on the advanced pop-down
button). This is NOT the default port associated with most LDAP queries. I
spun my wheels for quite a bit because part 1 was failing and I did not see
any documentation on Microsoft's Exchange/Entourage web pages that brought
out this simple and critical point. This seems to be the default setting
with Exchange.

The default LDAP port is 389 (636 for SSL). The global catalog (GC) port is
3268 (3269 for SSL). This is an Active Directory thing more than an Exchange
thing. The former contains domain-specific details. The latter contains
replicated data from across the forest.
3) The delegation need for SSL and a certificate on possibly a DIFFERENT
server from the frontend server needs to be highlighted. We wasted a lot of
time and resources trying to track that down and we still have this
certificate warning problem remaining.

I recommend that Microsoft develop at minimum a simple troubleshooting web
page that at least provides a little direction to help speed up the process
of implementing Entourage. There would be less head banging and one step
forward, two steps back. They might start with the above points and include
others such as to be certain that the email field in the Entourage settings
is in the form of "userid@domain" and not "emailalias@domain"

You have a domain where the user id is not the same as the email alias? We
should never be asking for the e-mail alias when we want the user id; either
we need to ask for the user id or we need to programmatically determine it.

Thanks for the feedback.
 
N

Nathan Herring [MSFT]

I haven't tested this out. Do PQDNs not work at all in Office applications?
(e.g., hyperlinks) Or is it this specific case?

Ok, so hyperlinks only take FQDNs, so that's not a good comparison. (Just
looked at RFC 1738).

I guess it would help me if you gave an example of the settings in the
wizard that do not work. I don't quite understand why it would look for
"bill.domain", if bill is a person and not a host...

-nh
 
B

Bill Bryson

Nathan,

Thanks for the detailed response. In answer to your question about the
reasons why the wizard fails if the exchange server domain is not in the DNS
is as follows:

First of all, sorry about using the example with my name (bill.domain) this
has nothing to do with user/persons. I was trying to be generic but a
better generic example would have been "servername.domain".

Check out my instructions for Entourage setup here to see what I mean about
how the setup wizard fails without the DNS (or Mac OS X client) supplying
the exchange server domain in the list of search domains:

http://www.tr.txstate.edu/css/email/entourage-exchange-setup.htm

Note how the setup wizards returns partially qualified names.

Bill
 
N

Nathan Herring [MSFT]

Ok, now I see what's going on.

First, I do not think we ever return a PQDN that isn't a simple host name,
and I mean we don't ever return "foo.bar" expecting it to be treated as
"foo.bar.baz.com" if "baz.com" is in your search domains.

It does look like this could stand some improvement. I don't think you
should have to add matrix.txstate.edu to your search domains to have the
account autoconfigure give you correct values. Part of that looks like
giving back FQDNs rather than simple host names.

-nh
 
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