After a month of no response from Apple on my MobileMe issues, I finally called them Friday the 8th of August, and insisted on receiving escalated support.
I spent two hours between giving meticulous notes of every step I had taken thus far, and going through various escalation "managers" etc...
They assured me that someone would CALL me back within 24 hours. I said specifically and directly "Don't lie to me here, tell me when they're really going to get back to me. If it's a couple days, I'll live with it; at least it'll be honest".
Again, they assured me it would be within 24 hours.
I then said specifically and directly "If I get nothing but an email from first level support suggesting that I repeat all the steps I've already taken, I'm going to be VERY angry".
Again they assured me I was at the second level of escalation, and that I would get a senior engineer, who would have read and researched my case.
Wednesday the 13th of August, I received the following email:
I was... displeased.
My name is Mike. I am a MobileMe Support Specialist, and it has been brought to my attention by AppleCare that you are experiencing issues with your MobileMe account.
I apologize that it took a little while to respond to you. As a result of the overwhelming interest in MobileMe, the MobileMe Specialist team is receiving higher volumes of email than normal.
If I understand this issue correctly, you are having trouble syncing calendars between Outlook and MobileMe. Please let me know the results of the troubleshooting in this article, including testing in a new Windows user if the earlier steps in the article do not resolve the issue:
MobileMe: Troubleshooting Windows Syncing
This will help isolate the direction of further troubleshooting.
It was also mentioned that you weren't able to reach chat support due the button always being unavailable, you may want to try clearing your browser cache as this sounded very unusual to us. Chat support is open from 8 am to 8pm Central Time every day.
MobileMe Support Specialist
I initially spent over an hour composing a very detailed two part reply, in which I went over all the steps I had taken and all the results I had thus far; as well as describing the customer support experience I had thus far, and how it was unsatisfactory, and against best practices of customer support and customer relationship management.
Only MobileMe ate it.
Oh yes, I forgot to mention, I received this email through the MobilMe account that I was having a problem with, and MobilMe mail went down several times during this time period.
Anyway, I decided to save my sanity and not attempt to re-write the long detailed email, and threw my hopes upon the wind, that someone had actually listened to the troubleshooting notes I had given.
"I just spent over an hour writing a very detailed and extensive reply, going into everything I've done, the results etc...Alas, my hopes were disappointed; though my expectations were satisfied:
I clicked the send icon, and my window blanked, only to come up with an empty reply form; and nothing in either drafts or sent items; even though I AM set to autosave drafts and sent items.
I'm even angrier than I was before... and that's really saying something.
Please, before we continue, read the notes I spent an hour and 45 minutes giving to the support specialist, customer support manager, and escalation manager last Friday please. They should have an extremely detailed account of what I have done, which includes everything in that link, and every other link I could find relating to the topic.
If those notes are not there... Well, I wouldn't be surprised at this point, but I would be even more irritated."
Honestly, I have to say that if I could have reached THROUGH the intertubes and choked the crap out of this person right then and there, I would have.
Please keep in mind that AppleCare Customer Relations is an administrative team whose primary focus is hardware repair administrative issues and is not a technical team and so they are not able to relay detailed technical related information that is as specialised as MobileMe. What was relayed to me was that you had done "all of the troubleshooting online" but the specific tasks and results -- especially of testing in a new Windows user -- was not available to me to review.
With composing a long email, you might not be aware that you can set up Outlook for Windows to send and receive your MobileMe email. You can find the details for this here:
It's amazing how one can be so dense, and yet be condescending and arrogant at the same time... while still being first level tech support....
Where does Apple find these people? I swear they must all be New York Actor/Waiter/Playwrights or something.
At any rate, I replied in more detail:
"As I noted last week, yes the problem occurs on a new windows user account, on several different windows computers, running XP, Vista 32, and Vista 64. I haven't tried it on my mac, because I don't run Entourage; but I need it to sync properly with Outlook.Unfortunately he never did clear out my original account as I asked, but he did create a nifty testing account for me to use, so that we could better isolate the problems.
I should note, iTunes direct sync with Outlook works just fine. I can sync calendars and contacts with no issues direct to iTunes and my iPhone. It is only MobilMe that has the problem.
Ive gone as far as setting up a test box with a brand new clean install of Windows, then installing Outlook and iTunes fresh and importing my contacts and calendar into a clean .pst file. Then I'll do a reset sync, and then a normal sync just to make sure. The sync always appears successful on the computer side, but may or may not populate the calendar or contacts on MobileMe. Sometimes the data populates sometimes it doesn't.
If it DOES populate the calendar and contacts, within an hour or so, for no apparent reason and without syncing again, the calendar and contacts will erase themselves off of MobilMe. If I have syncing enabled, they will also erase themselves off my iPhone and even out of outlook.
After that first sync, no later sync will populate changes, and doing a sync reset will have no effect.
Recently, the contacts stopped erasing themselves, though the calendar still does. Still neither will sync any changes after that first sync.
Just in the last few days, a new symptom has arisen, where suddenly for no apparent reason, I now have 10 calendars in MobileMe, all titled either home or work, all blank; and I cannot delete them or adjust any of their properties.
After the first sync working and subsequent failing, I have tried uninstalling all Apple software, going as far as going into the registry manually to pull it out; rebooting, uninstalling outlook, rebooting, then reinstalling everything cleanly on a different user account, and trying to sync, and again nothing. Then I try a reset sync, and a regular sync, and again nothing.
At this point my calendar and contacts database entries in my MobilMe account appear to be in an inconsistent state, and I believe they need to be cleared out from the server side, as I can no longer add or delete contacts or calendar entries, even manually."
I went through the suggested steps again only using the new testing account... nothing. I went through my own procedure again, nothing. I ran it on four different PCs, two XP, one Vista 32, one Vista 64, nothing. On each computer sync appeared to succeed, but at no point did MobileMe populate calendars or contacts.
In the meanwhile, I had tested calendar sync with Google Calendar Sync, various SyncML services, and a few others; and I found them all unsatisfactory, until I found Calgoo, which works a treat and lets you sync from multiple data sources, two multiple endpoints if you like; plus it's free.
So, all of the windows solutions worked to some degree or another, and Calgoo worked perfectly; ...so I thought about what was different between MobileMe, and the working windows sync apps.
The first obvious thing, is that the people who coded MobileMe, and especially AppleSyncAssist (the actual executable that does the sync for MobileMe) were very lazy, and not particularly competent (a well designed but poorly coded app is worse than the reverse)....
Ok, so what is MobileMe missing that is critical, necessary, important etc...
The obvious one is that there is no proxy support whatsoever; even though there is no reason not to have it. However in this circumstance, I wasn't testing from behind a proxy.
The other thing that I noted, was that you could choose to "sync with outlook", but it didn't allow you to choose what Outlook profile, mailbox, or folders to sync with...
Ooooohhhh, I think I'm on to something here...
You see, Outlook allows users to have multiple profiles, each of which has it's own sets of "folders"; and each profile can have multiple sets of personal information folders, that are stored together in a bundle file called a .pst. Although you can only have one profile open at a time, each profile can have several of these folder sets open at a given time (though your email accounts will always be set to deliver new email to just one of them).
Now, the default location in older versions of Outlook USED to be "personal folders", and if you upgrade from an older version, or if you create a "new personal folder file" the first time you start outlook, then that will remain the default location.
However, like most corporate users, I don't USE the personal folders as my default location. In fact, I don't even have a personal folders file, I use the Mailbox folder, which syncs with my corporate exchange server, and leaves the data up on the server. This allows me, and to a limited extent my co-workers (they can see my free/busy times on my calendar) to access my data from multiple computers, from web interfaces, and if I had a blackberry, through it as well. An offline copy is downloaded to your local installation every time you sync up, and is also stored in a local file, which sync programs should be able to access.
I had a thought... could Apples engineers be that stupid, lazy, and Apple centric.... yes they could.
My thought was simple. Apple programmed the MobileMe sync app to only check the "personal folders" file, and only the default profile for the user account (it's a registry setting that's invisible if you don't have multiple profiles); and if that set of folders didn't exist, the behavior was erratic.
Seemingly, MobileMe fell back on the default delivery location, but for some reason didn't treat the data appropriately if it wasn't from the "Personal Folders" file. Most of the time it wouldn't sync at all; but inexplicably, sometimes it would sync once, and then never again.
So, I did some experiments. I created a new personal folder but didn't name it "Personal Folders", and copied all my data into it then tried to sync.
Ok, then I changed the new folder to my default location and tried... still nothing.
So I then renamed my PST folder internally (not the file name; that can be anything you want) to "Personal Folders"; but didn't make it my default delivery location. Again nothing.
Finally, I changed my default delivery location to "Personal Folders". and suddenly, everything syncs just fine.
So I tried it on my other three boxes, and had the exact same results. None of them would sync properly without those settings, but they all synced perfectly with them.
So, MobilMe MAY be able to sync with your system in a way other than I describe, but its behavior will be erratic, and you may lose data. If you want to get it done right, you need to use "Personal Folders" in your default profile, named properly, and then set them to be your default delivery location.
Anything else, and MobileMe might decide to stop syncing with you, or just pitch your data with no warning.
Unfortunately, that was all in my test account. I still had the problem of the inconsistent database; so I went back to my clean box (virtual machines are so nice for that) installed Outlook and mobile me, and did a reset sync with empty calendars and address books, and all of a sudden no more 10 frozen calendars.
So, I now have Outlook on two computers syncing both with MobilMe, and with Goggle calendars using calgoo, so that I can share my synced calendars with Mel over Gcal. MobileMe DOES support calendar sharing, but only for iCal users. Great.
Honestly, this whole thing is a major feature incompleteness issue. The reason the windows sync programs allow you to pick specific calendars (and address books for that matter), is because Outlook lets you have multiple calendars. If you can't do the same, then really you don't support Outlook.
I was able to work around this and fix it, but many if not most corporate users don't have that opportunity... you DID want to get those users right Apple? After all it WAS part of your major push and all.
Finally, after more than a month, I can now sync wirelessly with my iPhone, and across multiple computers; with secondary sync to Google for shared calendars.
Now Apple, the whole world needs you to fix your Outlook support; and I specifically need calendar sharing for those of us who don't use iCal... Oh and basically every corporate user needs proxy support.
... Oh and a teensy bit of reliability please? Thanks.