Morning has broken

A technological lament in eight Tweets.

1 – Since Leopard time-stamps differently, syncing iPhone between Leopard + Tiger Macs means constant “replacement” of same files.

2 – 365 “old” calendar events get deleted; 365 “new” ones replace them. Same with 1GB video files. “Old” one is deleted; “new” one gets written.

3 – “Calendars” and “subscriptions” are also different between Leopard and Tiger, causing data loss when you sync.

4 – Choices: Update all Macs to Leopard (even though CS3 is wonky in it). Or sync iPhone only to one Mac (home OR office, not both). Or buy PC?

This would seem to end things. But then JZ pipes up:

(5) – : @zeldman – Seems to me that you need .Mac. Sync your phone to just one computer and then sync both computers to .Mac.

So one wearily continues:

6 – .Mac sync fails between Leopard + Tiger due to changes Apple made between OSes. .Mac freezes instead of syncing. .Mac useless now.

7 – Obviously Apple requires you to “upgrade” all your Macs to the same OS version, otherwise everything (including iPhone) is half-broken.

8 – It’s the kind of stuff that’s supposed to happen to the John Hodgman (PC) character, not the Justin Long (Mac) guy.


[tags]getamac, justinlong, johnhodgman, mac, pc, sync, dotmac, .Mac, iphone, leopard, tiger, iphone, compatibility[/tags]

37 thoughts on “Morning has broken

  1. Weird. I was actually shocked at how *well* Leopard and Tiger synced together for the month long period when I did that. Didn’t have any problems at all. Now that all of my computers are on Leopard, however, I *do* have the replace-all-calendar-entries-every-time problem when syncing via .Mac. Oh well, at least it’s non-destructive. Just an extra confirmation box to check.

  2. Jeffery, it’s time for you to buy a PC equipped with Windows XP. Or consider a career in which a retractable ballpoint is the most technical gadget you are forced to deal with.

    For what it’s worth I have never had a major issue with any Mac I’ve owned, and my Leopard and Tiger Macs sync pretty easily, but for the holy love of god I’ve never read someone with as many issues in the land of Apple as you. Maybe that or it’s time to also blog about the positive experiences? Or at least drop some of the hyperbole.

    My floats create extra margins in IE 6. The web is useless now.


  3. My floats create extra margins in IE 6. The web is useless now.

    Hyperbole hit noted and taken. But it bothers me when something so beautiful and so well-considered in nearly every detail gets part of the experience wildly south of the mark.

    It’s like looking at a beautifully designed web page that is wonderful in almost every way, except that, inexplicably, the designer chose to stick a big honking “under construction” animated GIF in the middle.

    Or like looking at a beautifully designed web page that is wonderful in almost every way, except that, inexplicably, the designer chose to set the initial headline in MS Comic Sans and wrap it in MARQEE tags.

    Mediocrity brings scant criticism, because no one cares.

    Genius that fails inexplicably earns harsh censure which sometimes bleeds over into hyperbole.

    If the user experience overall weren’t so freakin’ wonderful, the stupidity and frustration wouldn’t bother me. I’d just expect it. Most computing systems (no names please) are badly designed. Most users expect a bad experience. They muddle through as best they can.

    People who choose Macs do it because design (broadly and more modernly defined to very much include USER EXPERIENCE) matters to them, elegance of user experience matters to them. Most of the time, Apple delivers — in spades.

    When they fail, it feels wrong.

    I also acknowledge that it happens to me more often that it happens to other people I know. And it’s not just Macs.

    My home cable modem can’t send mail unless you configure your outgoing mail setting a certain way; the company doesn’t tell you about this. But my friend who uses the same service just sends mail without configuring the outgoing mail to match the company’s requirement. Why does it work for him and not me? I don’t know.

  4. It is well-documented that the technology gods pick certain unfortunate souls upon which to lay curse after curse. Printers, for example, turn off, break, or have paper jams whenever a friend of mine so much as touches them.

  5. Some people have the anti-technology curse. Apparently you’re one of them, and that’s sad. It’s amazing what you’ve done in light of that though! ;-)

  6. I was having some of the same problems that you’ve been experiencing, and they were driving me nuts. Then I went and looked at my keychains and preferences, since Leopard now syncs preferences and has done keychains forever. Wow did I have a ton of crap in keychains – cleaned that stuff out and it’s faster to sync now by far.

    And then preferences. I work in Final Cut Pro daily and when that program has a failure, it’s been a truism since the 1.0 days to delete the preferences file because it’s become corrupt and move on with you life. And while that’s just one instance, I realized that I might have cruft in some system preference which, when I think about it, I haven’t deleted or modified by hand since 10.3.something. And the differences between 10.3 and 10.5 are extreme enough that if something came over, during the migration from one system to the next an old preference file got copied to the new system, well, it might just break something.

    So I trashed them, removed from .mac sync, and started anew. Amazingly, no new syncing problems have come up, and I’m no longer plagued by random requests to delete and restore data.

    Of course, I still can’t get Transmit favorites to sync to my MBP, but Panic knows of this and is working on it.

    So I thought I’d let you know that bit of wonderment.

  7. I also acknowledge that it happens to me more often that it happens to other people I know. And it’s not just Macs.

    My significant other has these sorts of problems. The general consensus of our group of friends is that he has some sort of weird electrical field that makes computers, etc. go berserk.

    If I had a nickel for every time I’ve ended up saying “it doesn’t do that when I use X”, we would be able to retire and have other people use our computers for us. :)

  8. I’ve always believed it is the ghosts of Luddites, trying to cause enough frustration that you’ll to pick up a hammer and start smashing machinery.

    As for the stuff about “get Windows”. Backward compatibility is one of the reasons Windows has had so many problems. Each new version of Windows inherits some bad code from old versions.

    Windows is fat and ugly with zits on its butt. OS X is skinny and beautiful… with zits on its butt. Whatever OS you choose, you’re going to have to deal with the butt zits when you two get intimately acquainted.

    Me, I never buy a car in the first model year (almost guaranteed to have electrical or mechanical bugs that weren’t fully worked out) and never upgrade to a brand new OS before the first “service pack” or X.2 or X.3 version is released (same reason).

  9. Or sync iPhone only to one Mac (home OR office, not both).

    Syncing the iPhone to multiple machines is not supported in any standard configuration. What kind of workaround are you using to allow this? I’d start the debugging process there.

  10. I noticed posts along the way here to the effect that there is something wrong with you (the user) and/or your karma. I’d like to point out that one of the reasons IT industry people tend to avoid the platform is precisely this: When things go wrong (and they do more often, naturally, since the inception of OS X with its greater power and flexibility), when all else fails you blame the user. This attitude also permeates the people who answer the phone and respond to emails at Apple.

    While it is sometimes the case that we users screw things up, the answer and the attitude are not useful to anyone. It’s just smug (even when intended in fun). This is why “Cult of Mac” is common currency.

    Jeffrey, your reference to the commercial and the roles PC and Mac play there is very apt. As Windows gets more Mac-like (at least in terms of appearance and user expectations) the Mac world is getting more Windows-like. Perish the thought. Demand better of Apple.

  11. I’ve owned Macs and PCs, but either way you’ll end up doing some troubleshooting regardless. They both have their problems — it’s just that they have different problems than each other. But take heart: fixing issues on either Mac OS X or Windows tends to be a lot less painful than troubleshooting Linux.

  12. One source of freezing and crashing on the Tiger Mac is a mysterious update message that arises when syncing the machine to .Mac (or to the iPhone).

    Removing .Mac preferences and rebooting the Tiger laptop enables the machine to reset once and sync once. But the seemingly successful sync is followed by the recurring pop-up of a message concerning “,” software that apparently controls RSS in Safari (for anyone who reads RSS in Safari) and should, under normal circumstances, operate invisibly from the user.

    While the popup is active, the machine has no memory to run any other program. It’s five or ten minutes of spinning beach balls. You can’t even cough up a force quit.

    Removing .Mac sync preferences doesn’t cause the popup to appear; removing .Mac sync preferences merely allows the machine to sync to .Mac once without freezing. The “” popup occurs whether sync is successful or not.

    The popup appears and asks if one wants to “allow” to “access the same keychain items (such as passwords) as the previous version.”

    If you click “Don’t change,” the dialog goes away (although it returns later at random intervals, sucking all the system’s memory away).

    If you click “Change All,” the dialog box stays on your screen pretty much indefinitely, while all the memory of your computer is sucked into a black hole. Eventually you force quit (although even invoking force quit can take many minutes), restart, and work for a short while before the idiot dialog reappears.

    Somehow updating to 10.4.9 made this useless, memory-sucking, machine-freezing application error pop up whenever the machine syncs to .Mac or the iPhone.

    The experience is, no offense to Windows users, like a bad experience in Windows.

  13. There’s no question that Leopard is an incredibly buggy release from Apple. Like Mr. Z, I’m finding myself (a relatively recent switcher from PC land, around 10.3) pretty dismayed at Apple’s seemingly cavalier approach to breaking their systems. What kind of QA was done before releasing this OS?

    Apple is a victim of their own success. Tiger was so good, and the experience using it so seamless, that Leopard’s flaws stand out all that more obviously.

  14. Every time I have trouble with .Mac sync it makes me feel totally helpless. It seems to be the one thing which makes someone like me, an avid and know-it-all about Mac user into a helpless simpleton. I had some of the same problems with syncing two 10.4 machines with my main Leopard machine not too long ago.

    The solution for me was to unregister all the machines from the Leopard .Mac Preference Pane. When you do this, you will actually get a dialog asking you if you would like to delete all the info from the .Mac servers. Confirm and then walk away or reboot.

    Take your Leopard machine and then turn on sync again. Have it sync all your information. Wait a bit and then see if it syncs. If all is well so far, walk away or at the very least do not attempt to sync anything with your Tiger machines. This little tip is what I think saved me and was suggested by .Mac support. Every other time I tried these steps, everything always failed. Register the tiger machine and sync. In my case I asked the Tiger machines to replace everything on the computer with info from .Mac. Hopefully all goes well.

    A couple of other points. Your login keychain has any entry with Type > .Mac Password. If this entry becomes corrupt you will get stuck in loop hell every time you try and open the .Mac Preference Pane. The only solution is to Force Quit the .Mac Preference Pane. Delete this keychain entry and then reenter it into the .Mac Preference Pane. I suggest if you get to this point to enter the password, make sure .Mac logs in and then close the preference pane to make sure it writes the password into your Keychain. .Mac sync is really the only thing that has consistently given me trouble since its inception. Although I always am able to fix it, it just shouldn’t be that way. Good luck.

  15. Well, at least Apple shows why proprietary (and closed) means inconvenient and bad. And although Windows would be able to sync better, I don’t think that’s the way to go.

    But finally, customers of Apple are finding that something does not work as it was supposed to do? Well, pay another $200 bucks to Apple and you can sync alright, is that so? No backward compatibility? Isn’t that called blackmailing?

  16. So a man who’s going to do some work in our new home calls to schedule the job. I’m at home, standing beside my laptop, but I can’t consult my iCal calendar because the laptop is frozen in yet another abortive .Mac sync attempt. The man has been hard to get hold of, and his services are much in demand. I agree to the dates and times he suggests, not knowing if I can actually do them or not. I jot the information down on the back of a Christmas card.

    Later, when I’ve unfrozen my laptop and restarted to stop the endless loops from sucking its memory into a black hole, I have the opportunity to enter the man’s contact information into Address Book and his dates into iCal. But I don’t do so.

    The reason I don’t do so is, if I enter this home-repair-related information into my home computer, I will lose the data because .Mac sync is broken. I’ll have to carry the Christmas card to my office and transcribe its information into my office computer, then sync my iPhone to my office computer, and either train myself not to use the iCal in my home computer or engage in further tragicomic attempts to get .Mac sync to work.

    Hardly a life-or-death dilemma, but definitely not the seamless home/office/anywhere digital lifestyle experience I paid for when I bought an iMac, a laptop, an iPhone and .Mac. That’s the point.

  17. Just the tip of the iceberg IMHO. I “downgraded” from Leopard to Tiger last night, only to find out that File Vault uses a different sparse image format that can’t be read by Tiger (shame on me for not turning FV off first). My suggestion for anyone who asks is to avoid Leopard. This must be how Windows Vista users feel.

  18. Funny that you said that. I’m reading this post because I needed something else to do than be frustrated with my work PC which is currently preventing me from finishing up a new site. Good luck with your phone!

  19. (Forgot to add the quote to my last post, my apologies for double posting)

    “The experience is, no offense to Windows users, like a bad experience in Windows.”

    Funny that you said that. I’m reading this post because I needed something else to do than be frustrated with my work PC which is currently preventing me from finishing up a new site. Good luck with your phone!

  20. You, sir, have bad Mac-fu. Burn some sage, or maybe light some incense in front of a shot of Steve Jobs?

    Hoping things get better for you. :P

  21. Is it just me or is the Mac starting to feel like the PC days of post-Windows95?

    I’m increasingly frustrated by Mac things feeling a lot less “Mac.” It’s not necessarily a Leopard thing, but since switching to Intel I’ve noticed a lot more flaky behavior of apps. BBEdit crashed last nite and it’s NEVER crashed in the 5+ years I’ve been using it. All CS3 apps crash; interface elements are broken (input boxes in the top toolbar for example); more and more dialogue boxes are appearing.

    This is the whole reason I switched in the first place!! It was a simpler life; now it’s back to being complicated and frustrating. What can we switch to now?

  22. @ this comment and this one too

    I’m confused; I thought you guys were catechized to say stuff like “it just works”.

    Wish I could feel sorry for you, but the fanboys have turned me into such a hater. Long live the PC!

  23. I’m surprised by how many people here have been having issues with Leopard.

    I’m incredibly impressed by how flawless my Leopard experience has been. My family is a six-Mac household, mixed PowerPC and Intel and Leopard has been the smoothest update I’ve ever had to deal with (I experienced some keyboard issues that have since been resolved with a software update).

    FWIW, Leopard handles all the web apps I’ve been able to throw at it (including CS3); I’ve been pretty happy with it. I doubt upgrading would help you much with your home PC though. Sounds like it could use a Clean Install with as little of your Home directory brought back across.

  24. Tomorrow I’m off to see an Apple genius with exactly these problems. I can’t get sync to upload my contacts/calendar from my Tiger iMac G5 let alone download them to the new Intel MacBook Pro. iTunes copies stuff to the very new iPod Touch (wonderful piece of kit!) but I have paid good money for .MAC and would like it to do something useful. If the genius fixes things I’ll report back.

  25. The truly sad part of this lament is that, 7 months later, IT REMAINS COMPLETELY VALID!


    Tiger-based iMac, Leopard-based MacBook, v2.0 iTouch… push from the .mac wiped my touch clean b/c I’ve not successfully logged into .mac/ from the iMac (home-base for the Touch).

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