Setup

• It’s brain-dead. It uses Autodiscover, so e-mail and password is all you need. You get prompted if you’d like it to also configure iCal and your address book.

• I haven’t tried from home yet, but the external server path is not filled out. Internal picks up EWS/Exchange.asmx URL just fine, but external is blank. I double-checked our Exchange server and this parameter isn’t filled out so that makes sense. The difference here is Outlook assumes the external is the same as internal if this value is blank, but it appears Apple Mail will not. Be sure to set your –ExternalURL parameters on the virtual directories appropriately.

Mail

• Responses to meetings come across as an .ics attachment, no special functionality here. This is especially bad if someone proposes a new time.

• The Exchange RSS Feeds folder does not integrate with the RSS feeds section in Mail. This would have been nice.

• Name suggestions are offered from the GAL and your contacts.

• Rules do not sync.

• UM voice mails have a built in media control. My codec is set to G.711 and I see embedded QuickTime controls in the message for playback.

• The actually listing of your notes is displayed in the Marker Felt font. It’s horrendous and tough to read.

• No out of office assistant.

• You can add multiple Exchange accounts.

iCal

• You can schedule meetings and invite attendees.

• You can view free/busy details for attendees.

• iCal does not differentiate between people and resources as attendees.

• You can view responses for meetings. Accepted, tentative, declined or unknown.

• Tasks sync to iCal “To-Dos”. The default view shows all completed items. Hit the iCal preferences to change this view.

• You can view Delegate calendars and grant access to your calendars and tasks.

• Name suggestions are offered from the GAL and your contacts.

Address Book

• My contacts came across just fine.

• I can’t see the GAL for some reason. The URL in the account settings looks correct, but the GAL is empty. Really strange considering I get GAL-suggestions when typing names in other applications.

I’m sure there are more to come, but despite some of the caveats this is still a huge improvement over Entourage. I’m looking forward to the Outlook for Mac client coming next year, but until then I’ll be using the native applications.

There’s no direct statement other than “Messenger for Mac 7.0.2 improves overall quality and conversations with Microsoft Office Communicator 2007 R2”, but I’m assuming this is a required update for a Mac client to connect to an R2 Front-End. Even if it’s not required it sounds like a good idea to have your clients on it.

Download link: http://www.microsoft.com/downloads/details.aspx?familyid=86ae6ab4-f766-4246-831e-dc5dbdbe4757&displaylang=en&tm

Hallelujah. Some decent support for Exchange on the Mac side. Significant changes include:

• Enhanced Autodiscover service to keep user account settings up to date after the account setup.
• Synchronization between Exchange Server and Entourage 2008 Notes, Tasks, and Categories.
• Addition of an Enable Logging (troubleshooting) preference, to log all events that can be used as diagnostic information.
• Use of attachments in Entourage for Exchange calendar events.

At a minimum you need Entourage 2008, but what version of update rollups your Exchange server needs to be at is a little confusing. The blogs say Update Rollup 4, but when you fill out the survey to get in the beta it says Update Rollup 5. I guess I’d go better safe than sorry and assume Update Rollup 5 at this point.

You can sign up for the beta here: http://www.microsoft.com/mac/itpros/entourage-ews.mspx

One of my pieces of OCS testing involved putting it through the paces of various IM clients other than Office Communicator and seeing what works and what doesn’t work so well. Even though I’ve read several pieces stating that Mac Messenger 6.0.3 was supposed to work with OCS, I cannot find a way to do so. This was all strictly for internal testing, but I imagine at this point the external results would have been the same. The first step was importing the root CA certificate into my X509 anchors keychain. After importing the certificate I could see it listed so I knew Messenger should be able to connect at this point.

Scenario #1 – Enhanced Presence: My first attempt was with a user that already had signed into an OC 2007 client, so enhanced presence has been enabled for this user. Messenger throws back and error to me "Sign in to Microsoft Messenger failed because the service is not available or you may not be connected to the Internet". I know both parts are untrue – I’m on the LAN with no issues and the service is certainly available because other users are signed in at the same time with Office Communicator clients.

Scenario #2 – Fresh User: I had a hunch that enhanced presence might be causing the problems so I created a fresh user account and enabled it for OCS. I purposely did not sign-in to an Office Communicator 2007 client so enhanced presence would not be turned on. After trying to sign-in with the new user I received a different error: "Sign in failed because the password is incorrect or the sign-in name does not exist." Again, I know both of these are untrue (Can someone give the MacBU some lessons on writing error messages please?). The password is correct and the sign-in name does exist.

I figured I’d take a look at what was happening on the server side of things so I started up the OCS diagnostic logger, checked the SIPStack option and started logging. For scenario #1, I saw what I expected: a normal NTLM handshake attempt, but instead of succeeding the final message is "421 Extension required" error:

Start-Line: SIP/2.0 421 Extension required
ms-diagnostics: 2013;reason="msrtc-event-categories extension required";source="tap-ocs-2k7.ptown.com"
ms-diagnostics-public: 2013;reason="msrtc-event-categories extension required"

Ok, fair enough. The Mac Messenger client probably can’t handle enhanced presence just like the Office Communicator 2005 client can’t. The extension the server is asking for is probably enhanced presence related. So on to scenario #2 with a new user account. This is where is gets confusing – I receive a "404 Not Found" SIP error this time:

Start-Line: SIP/2.0 404 Not Found
ms-diagnostics: 4005;reason="Destination URI either not enabled for SIP or does not exist";source="tap-ocs-2k7.ptown.com"

Well, at least this error message is somewhat consistent with the error the user receives from Messenger. I know the URI exists and is enabled, so this error is bizarre. Just for kicks I opened an Office Communicator 2005 client and tried to sign in. Guess what? It worked fine. Maybe I needed to sign in to OC one time to make this work? Nope. I still can’t sign in to the Mac client.

So my conclusion from all of this is that having enhanced presence enabled probably prevents a user from ever signing into a Mac Messenger client, or at least until Microsoft’s MacBU releases the next version of Messenger. A user without enhanced presence should probably be able to sign in successfully, but I’m not sure why it doesn’t work. Has anyone out there gotten the Mac Messenger client to work with OCS 2007 yet?

Update:

I got it working! To be able to use Mac Messenger 6.0.3 you must first create the user on the OCS pool and then enable their account for Enhanced Presence. At that point they should be able to sign-in successfully. You can read my post about the different stages of Enhanced Presence for some more information.

One of the changes with OS X 10.5 Leopard is the lack of the X509Anchors keychain being installed by default. The problem this creates is that a lot of Microsoft applications for the Mac depend on this keychain for their certificate authentication. They check the X509 keychain for a certificate and when it doesn’t exist, they fail to authenticate. The annoying part here is that the application doesn’t even have appropriate error messages included. Instead of something logical like the "the certificate is not valid or trusted" the user gets an error that their sign-in name or password is incorrect. Fortunately there’s a workaround and you can add this keychain back to make it functional again.

1. Open Keychain Access (Using Spotlight to search for it is probably easiest)
2. Click File > Add Keychain
3. Browse to Machintosh HD | System | Library | Keychains and select the X509Anchors keychain. Press Open.
4. Now select the X509 keychain in the Keychain Access window and drag all of the certificates you need onto this window. You should be prompted for your admin credentials.
5. Now you’ll see a window asking which keychain you want to install the certificates to. Choose X509Anchors and press OK.
6. Once your certificates are installed, try signing in again. This time it should succeed!