Snow Leopard with Exchange support not working

Ugg. Well, I give up. I think I meet all the minimum requirements. But it still won't work. No matter what I try - no dice. I even tried putting four letter words in for my settings. Needless to say, it didn't work well.

I just read through this entire thread (whew!), and, as the lead admin for an Exchange 2007 setup, I'd like to clarify some information that I see being a little off-base, and also just some general information about Exchange 2007 and how it is (can be) set up. I realize that this honestly has very little to do with the problem at hand, but I see a lot of confusion that I'd like to clear up. Feel free to completely ignore this post. 🙂

First, ActiveSync is not Exchange Web Services. Nor is it MAPI. Or Outlook Anywhere (the new name for RPC/HTTPS). All of these protocols are different, and have different uses. ActiveSync is for mobile devices to connect to Exchange. The underlying protocol makes it great for mobile devices to use because it helps to save battery life and uses less data than, say, using the full-blown Outlook Anywhere protocol (or even EWS). It does this by implementing a sort of keep-alive (or heartbeat) channel open to the server, with a looooooong TCP connection timeout (15 minutes or greater). This means that a device doesn't have to set up and tear down a connection to Exchange every time it wants to sync (expensive), and it also means that the device itself can leave the connection dormant instead of closing it (use less data, save battery) and the server can send data to the phone using that connection--instead of the phone requesting it--since the connection is already open. The device just has to send a heartbeat packet every so often (I think 5 minutes is the default) to keep the connection open. This is how the so-called Push technology works. Mail.app does not use ActiveSync, nor should it, for those who have suggested such. It's just not the right protocol.

So what should Mail.app use? Either Exchange Web Services or MAPI / Outlook Anywhere. Let's address why it probably isn't using MAPI / OA first. MAPI is a proprietary protocol (yes, it has been reverse-engineered: do a search for the "openchange" project), and as such, I doubt Microsoft really licenses that out. Outlook Anywhere is basically MAPI data being encapsulated within the HTTP(S) protocol, meaning that Outlook can connect to the Exchange server from anywhere in a much more secure manner (MAPI is an RPC protocol: yes, the same protocol for which Microsoft releases a security patch about every week. RPC should NEVER be available from the internet.). What you do get with MAPI / OA is the "full" experience of an Exchange implementation, if you will--things like the server "pushing" data to Outlook instead of the client polling for new data are included with this.

So the choice that is left to Mail.app is Exchange Web Services, and this is a good choice. Anyone can develop against it, and it uses open standards (do a search for SOAP) to make it all happen.

I have seen some confusion about Entourage and its capabilities. Without the EWS update, Entourage 2008 (and the previous version) uses the WebDAV protocol to talk to Exchange. (Yes, I left it out up at the top. No, it wasn't a mistake. Microsoft is trying to get away from WebDAV in all of its products.) Exchange 2003 and 2007 both speak WebDAV (probably 2000, too, but I don't remember), so Entourage would work just fine with that. The EWS update for Entourage 2008 adds the capability to use Exchange Web Services instead, which is a vast improvement over WebDAV.

With the above being said, let me make some statements.

- Just because your iPhone works doesn't mean Mail.app will work. Or Entourage, with or without the EWS update. Heck, it was probably two different teams working independently of each other, coding against two completely different protocol stacks.

- Just because EWS is enabled by your Exchange admins doesn't mean it will automatically be available outside of your company. This is completely dependent on what the Exchange admins (or more accurately, the security team) have opened up to the outside.

- Just because Outlook works doesn't mean Mail.app will work. Outlook uses the MAPI and Outlook Anywhere protocols, not EWS.

- Just because Entourage works doesn't mean that Mail.app will work. Those are two different products, written by two different teams, and it's entirely possible that one app may have bugs in it that the other one does not. In this case, it seems that Mail.app may have a few bugs in it that Entourage was not blessed with.

...for those of you still reading, yes, I finally got around to something relevant to the thread at hand! I'm typing this post on a MacBook Pro that absolutely REFUSES to connect to my Exchange mailbox--Mail, Address Book, and iCal all crash horribly when it goes to autodiscover our site's settings. Yes, Exchange is up-to-date. Yes, EWS is enabled--I use it almost every day for other things. Yes, Entourage 2008 with the EWS update works. Yes, I know EWS is available off-campus. (OH, which brings up another point: want to know if your Exchange 2007 environment is set up properly for off-site access to the various protocols, using both Autodiscover and manual settings? Try this site: https://www.testexchangeconnectivity.com/.) Whats interesting is that I have heard reports of other 10.6 users on campus not being able to connect, while some can. For us, it seems the difference is that those who upgraded to 10.6 are able to connect to Exchange using Mail.app, but those who installed fresh cannot. Weird? Yup.

Okay, that's all, I'm done. If you made it this far, I applaud you. I probably would have stopped reading long before now. 🙂

---
seth wright
windows / lead exchange engineer
james madison university

olivierzol wrote:
Active Sync is NOT only for MOBILE DEVICES.

Actually, yes, ActiveSync was intended only for mobile devices. I'm also not sure how your comments below state otherwise.

In addition to the ActiveSync desktop sync software bundled with Windows, Microsoft also uses the ActiveSync name to refer to the push messaging component of Exchange Server, which relays messages to mobile devices (we don't need the push part for Mail).

Yes. You're talking about two different products branded with the same name.

Microsoft ActiveSync is the desktop application (called Mobile Device Sync or something similar in Vista+) used to sync PDAs and the like to your desktop. You can use this to sync with Outlook, no matter what your underlying email account is. Normally this is used to sync devices that either cannot sync over-the-air (OTA), or if you are not syncing against an Exchange server but still want to sync Contacts, Calendar, etc. with Outlook.

Exchange ActiveSync is the protocol that enables mobile devices to synchronize with Exchange OTA.

This being clarified, why can't I simply use my OWA address to configure Mail ?

What did you clarify? And why do you think this {would,could,should} work? The FQDN for your OWA server may not be the same as the FQDN for EWS. It's not in my environment. This is what Autodiscover is for--it should tell the client exactly where each service is located, without the user having to know the information. This is what Mail.app tries to do (I guess...haven't actually gotten it to work yet).

---
seth wright
windows / lead exchange engineer
james madison university

"Mobile Device" is ambiguous. My laptop could be considered a mobile device, so could my Playstation. They are just computers. My iPhone is a computer, my desktop is a computer- they probably have pretty similar kernels. Just because something is "designed for a mobile device" doesn't mean much - go setup exchange on an iPhone simulator and it will work on a desktop, which is not a mobile device.

The point is, ActiveSync works great, and millions of people have figured out how to access their email and calendar using it. It could have worked on the Mac, too. I understand that it is not the best solution, and that it isn't designed for it, and it isn't as fully featured, secure, etc. etc. etc. But it works, and as such the iPhone is compatible with a much larger set of exchange configurations than Snow Leopard. A MUCH larger set. And that's all people want - to see their email and their calendars.

The reason Apple didn't use ActiveSync on the Mac was more than likely because Microsoft wouldn't license it to Apple to be used in such a way. After all, it's not what it was designed for. It was designed for a mobile "device". Not a computer.

homerZ wrote:
"Mobile Device" is ambiguous.

In this context it really isn't.

The point is, ActiveSync works great, and millions of people have figured out how to access their email and calendar using it. It could have worked on the Mac, too. I understand that it is not the best solution, and that it isn't designed for it, and it isn't as fully featured, secure, etc. etc. etc. But it works, and as such the iPhone is compatible with a much larger set of exchange configurations than Snow Leopard. A MUCH larger set. And that's all people want - to see their email and their calendars.

I cringe at that paragraph. I manage ActiveSync clients differently than full-featured clients like Outlook, etc. I could have one CAS cluster set up just for OWA, one set up specifically for EWS / Autodiscover / OA, and a third for ActiveSync users with differing ACLs around each. Now you're telling me that I should expect fat clients on my ActiveSync node? You'd have one unhappy Exchange admin.

Just because something works doesn't mean that it should be used everywhere. Right tool for the right job and all that. Besides, I don't know what subset of operations are allowed / implemented over the ActiveSync protocol, but I can almost guarantee that it is nothing compared to what you can do with EWS. Go browse through http://msdn.microsoft.com/en-us/library/bb408417.aspx and you'll see just how powerful and flexible EWS is.

Again, just because something "works" in one context doesn't mean it should be used in other contexts. You don't build your next killer feature by abusing one protocol when another one exists *exactly for your purpose*.

The reason Apple didn't use ActiveSync on the Mac was more than likely because Microsoft wouldn't license it to Apple to be used in such a way. After all, it's not what it was designed for. It was designed for a mobile "device". Not a computer.

You kind of made my point for me here.

Honestly--the question is not "which protocol should Apple have used?", it's "why are people experiencing issues if the build was properly QA'ed and vetted?" You can say all you want about how they could have made it work, but until you've set up and administered the environment and understand how everything works together, please refrain from making these kinds of comments.

I don't know what subset of operations are allowed / implemented over the ActiveSync protocol, but I can almost guarantee that it is nothing compared to what you can do with EWS. Go browse through http://msdn.microsoft.com/en-us/library/bb408417.aspx and you'll see just how powerful and flexible EWS is.

EWS may be powerful and flexible, but until everyone upgrades their servers with this powerful, flexible new software, it does nothing for me, because I can't even check my email- the most basic of tasks. The end users usually have little control over the upgrade plans of the exchange admins in their place of work. I am sure Microsoft would love everyone to realize how much potential EWS has and have them upgrade. But I am looking for the functionality (that Apple has promised in Snow Leopard) now, not in 2 or 3 years. I am also looking at this from the POV of a consumer, not an exchange admin, and I have a valid point. I would be thrilled if I could do on my Mac only the limited functions I can perform on my iPhone.

Again, just because something "works" in one context doesn't mean it should be used in other contexts. You don't build your next killer feature by abusing one protocol when another one exists *exactly for your purpose*.

It may exist for this purpose, but too few companies have adopted / configured for it - there are a lot of great protocols that exist but if no one adopts them, then they aren't very useful to the majority.

After all, it's not what it was designed for. It was designed for a mobile "device". Not a computer.

You kind of made my point for me here.

Actually, I was being sarcastic there. There is no difference between a mobile device and a computer from a software perspective. Maybe less time should be spent by exchange admins trying to decide complex new ways to treat them differently!

...until you've set up and administered the environment and understand how everything works together, please refrain from making these kinds of comments.

You're right. I haven't administered an exchange environment, so I shouldn't talk. Neither should the thousands of other users like me who purchased Snow Leopard thinking they could connect to their email and calendars but cannot. We should all shut up and be grateful that Apple and Microsoft agreed on such a powerful and flexible technology, and look forward to the fact that we may possibly be able to take advantage of it in the next few years. Just for clarity- I am being sarcastic again.

OK - now I've gotten defensive, and I've side tracked from my original point. I don't want to argue over technical details anymore. I don't want to pretend like I know more about exchange than an exchange admin. I don't want to argue that ActiveSync is the appropriate protocol- I agree that it isn't. But, I cannot access my email or calendars until the exchange admins at my work upgrade our perfectly good, working exchange 2003 setup. With todays budget constraints, that could be in 2 years, or it could be never. I have NO control as an end user, and I imagine there are thousands and thousands of people in my position.

This isn't like downloading a new browser, installing a new OS, or even buying a new computer. The end user has NO control here- if I want exchange on my mac I have to just wait - or use my iPhone simulator. I would argue that more people are in my position (exchange 2003 slaves) than there are people who are satisfied with Snow Leopards implementation (exchange 2007 w EWS).

On a side note, I in no way doubt your knowledge of exchange. You sound like you know what you are talking about from the POV of an exchange admin. I am just giving you the POV from the client side - and there are a lot of us that feel this way.

Wow what a thread! I am not about to jump off into all the technical details. I understand most folks don't care about that, they just want to enter their email address and have it work. None the less I also understand that with some many variable into play that it just doesn't always work that way.

I recently signed up for a Go Daddy Hosted Exchange Server Email account (using my domain) It is so weird because I had to go through like 4 or 5 steps from setting up my DNS/XM Records, to even setting up my email account in the Exchange Management Console. None the less I got through it and low and behold, I've now used it to setup a Mac Mini and MacBook Pro using Snow Leopard. The auto discovery worked just fine and everything was setup within mere moment (like I said we just want to type our email address and have it work). Email, Calendar and Contacts all synced up just perfectly and my iPhone connects and it works as well.

It is possible there is a bug that Apple is going to have to track down on some of this. It is also possible that many of are trying to use Exchange servers that simply aren't setup properly. Clearly Go Daddy did theirs correctly. +1 for Go Daddy!

William Lloyd wrote:
The iPhone and Snow Leopard use TOTALLY DIFFERENT methods to connect to Exchange. So no, it's not reasonable to expect Snow will work, just because the iPhone does.

I disagree completely. That's the sort of implementation detail customers shouldn't have to care about. The iPhone OS upgrade I didn't have to pay for handles Exchange better then the OS upgrade I did have to pay for and whose Exchange support was the one new feature. To make it work differently than the iPhone is just stupid and frustrating for your customers, even if the implementation is better in some developer's estimation. This just doesn't jive with the whole "it just works experience".

So quit posting. No one's finding your condescension helpful and you refuse to acknowledge a valid point. Put away your IT hat and think from a customer's perspective - you know do the very thing that AAPL does better than MSFT. Maybe it helps to watch some of the Mac/PC commercials to understand the expectations AAPL has set. The point is customers don't give a flying hoot what the technical reasons are. The fact remains one AAPL product receives email from Exchange and one does not. PERIOD. It doesn't matter what the reasons are. It's bad business not to *at least* support that method as a fallback for your new and improved with better protocols and 100% passing unit tests very latest version of Exchange only method. As if corporate IT depts across the world rush out to upgrade their Microsoft products. Seen the installed base of IE in the wild lately? No matter how much you insist the problem is all the end users don't understand - the fact remains people have a good experience with iPhone OS - Exchange and not so good with SL - Exchange.

I'm following this thread more out of amazement than real need. I am truly dumbfounded at the inability of so many people to accept the cold hard facts.

First of all, no matter how anyone tries to say that all computers are equal, they are not. There ARE differences between a 'mobile' device and other types that are quite clear. A laptop may be 'portable' but wherever it is, it makes a connection and basically stays there. If it moves, the connection is broken and has to be remade from the different location. A 'mobile' device needs to be able to keep its connection up even while moving and even when that involves switching routes/pathways and this requires different techniques that are not required on any sort of fixed (even laptops) devices.

But, at the end of the day, it is not my interpretation of these differences that is important. We are talking here about connecting to Microsoft Exchange Server - the clue is in the title. This was written by Microsoft and everything about it is controlled by Microsoft. They are making the rules and they have defined 'mobile' devices as using a different connection mechanism and I've no doubt Apple are obliged to work within that framework. So if you are unhappy about the fact that Mail.app can't use ActiveSync, complain to Microsoft (and see how far that gets you).

In any case, this is not news. Even before the release of Snow Leopard it was well documented that it would use EWS and required Exchange Server 2007 and would NOT work on 2003 (apart from IMAP). Not only that, but Exchange 2007 needs the correct updates (Microsoft's responsibility again) and to be configured correctly for it all to work and this is 100% down to the Exchange admins. It is not the fault of Apple, nor any of the other posters here that some of these admins are unwilling or unable to do this and if you are in that situation, tough. That's hard I know, but it's no use complaining about it here. Ask questions about how to possibly help them to make it work, yes sure, but arguing the toss about how Microsoft have decided to categorise computing devices and implement that in their products is not productive and disrespectful of the knowledgeable advice and help being offered here.

Having said all that, there appears to be 2 problems involved here.

One is that many users are unable to get their Exchange Server configured as it needs, either due to their lack of knowledge or because they have no direct control of the server, both of which have the 'potential' to be solved by diligent perseverance. Although if the admin/owner of the Exchange server refuses to help, then I guess you're stuffed. Complain to them AND Microsoft.

The other issue is that in some instances, even though the Exchange config. is apparently correct, Snow Leopard refuses to work as it should and it appears that in many cases the apps will crash while trying to autodiscover. There's NOTHING that a user should be able to do that causes such a catastrophic result, whatever the configuration of the server, so this latter issue just has to be a bug and needs to be reported to Apple, by everyone who is experiencing it. How many have complained about this problem here yet not reported it to Apple? Remember, Discussions and Feedback are not synonymous. Apple do NOT actively read these forums. If you want to complain, report a bug etc, use Feedback.

Luckily my free Exchange Server account works OK, but I do sympathise with those who have problems. However, complaints need to be directed at the appropriate target.

You're looking a little foolish here. Someone with greater technical knowledge than yourself tries to help and against a barrage of complaints explains in simple terms how it is and you refuse to accept the facts and even insult them for trying to help. Shame on you.

But actually, in some ways you are correct. The technology IS unimportant. EWS, ActiveSync etc is of no concern to the end user. What IS relevant is that Microsoft (whose product this is all about) have specified how each device type should connect and it's not how YOU want it. Which is bad luck for you, but no amount of blustering here will change that.

Your problem is NOT with Apple, go complain to Microsoft.

What is amazing to me is how far off topic we all have gotten in this thread (myself included). I am sitting here reading the back and forth dialogue, which in actuality, is all pretty intelligent in my estimation. And everybody for the most part is making very valid points.

But perhaps these arguments are better suited for a different forum. That being said, I have given up on getting my Mac to integrate with our Exchange. For now, it will just sit there, envying my PC for its Exchange integration. Yuck. That sounds just plain sick to me! 🙂

Nicely summarised.

Has anyone, ever, found anything from Apple that details the setup that they recommend in order to connect to Exchange with SL? At least then we could refer to that as a starting point...

Man - I have tried so many different scenarios, I can't even recall what was official from Apple, and what was totally unofficial. Eek!

homerZ wrote:
...the thousands of other users like me who purchased Snow Leopard thinking they could connect to their email and calendars but cannot.

...But, I cannot access my email or calendars until the exchange admins at my work upgrade our perfectly good, working exchange 2003 setup.

From Apple's own page ( http://www.apple.com/macosx/exchange/) about Exchange connectivity in Snow Leopard:

Apple:
Now with Snow Leopard, the Mac has out-of-the-box support for Microsoft Exchange Server 2007, something even Windows PCs don't have.

Apple promised support for Exchange Server 2007, not any other version. They did not promise support for Exchange 2003 other than IMAP. They stated it on their marketing page.

homerZ wrote:
...This isn't like downloading a new browser, installing a new OS, or even buying a new computer. The end user has NO control here- if I want exchange on my mac I have to just wait - or use my iPhone simulator. I would argue that more people are in my position (exchange 2003 slaves) than there are people who are satisfied with Snow Leopards implementation (exchange 2007 w EWS).

I agree with you completely here. End-users have no control over what their IT department uses, allows, disallows, etc.--well, outside of voicing their opinions to said department. 🙂 And unfortunately, if your company is not running Exchange 2007, Snow Leopard won't net you anything. I'd feel more sympathetic, though, if "Exchange 2007" wasn't stated directly on Apple's page about Exchange support.

On a side note, I in no way doubt your knowledge of exchange. You sound like you know what you are talking about from the POV of an exchange admin. I am just giving you the POV from the client side - and there are a lot of us that feel this way.

I never thought you were--healthy debate and all, I guess. And I have been removed from the end-user side for a while; sometimes it's good to get whacked with the end-user-perspective stick once in a while. 😉

And with this, I believe I am done here. Still can't get my 10.6 install to connect, although others here can, with the only difference here being that they upgraded and I did a fresh install. I may try upgrading and see if it works then. If I have any other data points to offer, I may pop back in.

Good luck.