Wow. I’ve seen some pretty dismal web launches but I must say Apple and their MobileMe launch has become the colossus of debacles. After spending several hours (and I mean, literally, eight+ hours of off and on efforts) of trying to get my Outlook 2007 data to properly sync to MobileMe and to my iPhone, I am close to giving up.
Updated at 2008-07-17 @ 4:05 pm: It appears that it is working now! Wahoo! Resetting the sync history from the MobileMe control panel never worked, but I tried to reset my sync history from iTunes (Edit->Preferences->Syncing->Reset Sync History.) I then let the next automatically scheduled sync occur and it prompted me to choose what and how to sync. I told it to take my contacts on my PC and overwrite MobileMe and told the calendar to merge. When that finished, I logged into me.com and all my contacts were there! Next, I reset sync history again from iTunes and the next sync, I selected merge for my contacts and to overwrite MobileMe’s calendar with the one on my PC. That finished, and my calendar was updated, too. Keeping my fingers crossed!
At first, things seemed to go almost right. I followed the instructions to the letter … I synced my iPhone to my Outlook (on my laptop) using the normal, tethered way, then opened the MobileMe (MM) control panel, set up the sync (I’m just doing contacts and calendar) then clicked sync. After the sync finished, I logged into http://www.me.com and made sure my stuff was there. My contacts seemed to be all there, but my calendar had some issues. When I selected the calendar in me.com, it popped up the following error:
MobileMe Calendar could not start because it was unable to load any calendars from the server. Try reloading Calendar. If this problem persists, contact MobileMe Support.
[Go to MobileMe Support] [Try Again]
Clicking Try Again just repeated the cycle. Clicking Go to MobileMe Support simply loaded the calendar … with my data apparently intact. Go figure.
Thinking this might just be a non-issue, I next set up my me.com account on my iPhone, then told it to use the push contacts and calendar from that account. So far, so good. My contacts all dribbled away (panic!) then started to trickle back in as they synced from me.com. I checked my calendar on the iPhone and most of my events and appointments seemed to be there, too.
Aside from the calendar glitch I saw every time I logged into the me.com website, things seemed to be working pretty well. The problem is I took it one more step. I tried adding my desktop Outlook 2007 to the mix, hoping to get the Holy Grail … a single, merged set of contacts and calendar, synced across all my devices. The problem was that I couldn’t get a sync to finish without erroring on my desktop. They errored out with the following informative message: “The sync failed because of an error. Please try again or contact MobileMe Support.” Thanks for that. After about half a dozen attempts, I decided to remove my desktop from me.com and cut my losses.
The problem was my contacts were a complete mess now in me.com and on my iPhone, with dupes all over the place. I blew away my contacts in me.com and went back to ground zero: I wiped out all my contacts in the me.com account and on my iPhone; then on my laptop (using the MM control panel) I reset my contacts to have Outlook overwrite MobileMe. That sync finished without an error, so I logged back into the MM website hoping to see my contacts again … but instead, it said simply “You have no contacts.” Whah???
The next step I tried was to completely start over. I removed my laptop from syncing with me.com, turned off push contacts and calendar in my iPhone and logged into the me.com website and deleted everything I could. I tried starting at the beginning, adding my laptop first as I did before, except this time the sync didn’t finish. It errored out with “The sync failed because of an error.” Gah.
Being completely insane and expecting different results from the exact same procedure, I did it again. The sync errored out again, but while it was running something new happened. I tried to open the sync preferences from the MM control panel, and applesyncpref.exe crashed. Several times, in fact. Over and over, I tried to get back into the sync preferences and it would simply go away each time.
After about two and a half hours, the background sync process finally seemed to finish. I was able to open the sync control panel and it said it had successfully synced. I then went back to the me.com website and logged in. Guess what? “You have no contacts.” And the same error when accessing my calendar. When I add a contact from the me.com website, it shows up temporarily, but then if I switch to the me.com mail then back to contacts, it says “You have no contacts.” So now, I can’t even add a contact to me.com from me.com. Indeed.
I have also spent hours trying to look for answers in the Apple discussion boards, but they are having as much trouble keeping those up and running as me.com, apparently. Numerous times when trying to click on a topic, I would get an error message asking me to contact the system administrator. Ironic that part of the error message said to try searching the forums, but when you clicked on the link you got a message that search had been disabled by the system administrator.
What a pedestrian, amateurish launch, Apple.