is a blog about design, technology and culture written by Khoi Vinh, and has been more or less continuously published since December 2000 in New York City. Khoi is currently Principal Designer at Adobe. Previously, Khoi was co-founder and CEO of Mixel (acquired in 2013), Design Director of The New York Times Online, and co-founder of the design studio Behavior, LLC. He is the author of “How They Got There: Interviews with Digital Designers About Their Careers”and “Ordering Disorder: Grid Principles for Web Design,” and was named one of Fast Company’s “fifty most influential designers in America.” Khoi lives in Crown Heights, Brooklyn with his wife and three children.
For no good reason, I continually get my hopes raised up over the idea of clean, seamless synchronization across multiple databases and devices via my Macintosh. For example, I just want to be able to maintain a single store of contacts, at least, and have it reflected across all the various applications I use: Entourage and Apple Mail, iChat and Adium X, my mobile phone and my PDA if I ever use one again.
This just isn’t the reality, though, not even in the latest and greatest iteration of Mac OS X. In fact, if anything, synchronization has gotten markedly worse; not necessarily less reliable, but less sensical and more de-centralized. I realize there are several third party utilities designed to ameliorate the situation, but I’m frankly disappointed in the infrastructure that Apple provides in the operating system. We seem to be in a kind of transition with Mac OS X, an unfinished state wherein synching functionality, though perhaps more prevalent that ever before, remains regrettably paltry and conspicuously lacking for a clear interaction model.
Confusion Central
Below: this feature doesn’t live here anymore. Kludgism comes to iSync.
Before Tiger, Apple had placed a lot of emphasis on the synchronization benefits of its .Mac service, which allows users to manage contacts, bookmarks and calendars across multiple Macs through a software tool called, logically enough, iSync. Now, in Tiger, when you open iSync and click on the .Mac icon, you get a message that says: “You no longer synchronize information across computers using iSync,” before instructing you to open your System Preferences.
Moving that functionality to a preference pane might make sense, but it seems to be part of a change that’s confused and ill-planned at its core. .Mac allows synching across multiple Macintoshes, but to get that same information (or most of it, anyway) onto your Bluetooth phone, as I do frequently, you still use iSync. (And that says nothing about the apparently sluggish pace with which the company has been updating its synchronization profiles for newer Bluetooth phones.) You also use iSync to get that information onto your iPod, oddly. But if you have an iPod photo, as I do, you use iTunes to synchronize your photo library to that device — huh? Also, don’t get me started on the lack of a coherent method for managing text notes for my iPod, or for synchronizing music libraries or FairPlay licenses.
Once and Future Synching Strategies
This resoundingly clumsy change in the interaction model is indicative of Apple’s master plan for data synchronization, which is to say that they may have one, but it’s in serious disarray. With Tiger, the company has laudably opened its .Mac synching technology to third party developers, but it has done so without immediate attention paid to maintaining a consistent user experience.
None of the roles of its three principal synching applications — .Mac, iSync and iTunes — can be neatly summed up or conceptually understood without a low-level familiarity with the preference controls of each. What’s more, the fact that critical functionality is hidden away in preference areas is often a sign of poor experience modeling, and that clearly holds true in this case. The next major revision of Mac OS X may yet bring a revamped iSync that unites all synchronization within a cohesive strategy, but until then it remains, for a platform blessed by Steve Jobs, uncharacteristically inelegant.
Khoi, not sure if you noticed the latest iTunes update, but version 4.8 now syncs your contacts/calendar for you instead of using iSync. This solves *one* of the many problems you mentioned…
(Also, it plays videos… one can only guess that it’ll soon sync them to your video iPod 😉 )
I hadn’t seen that. Is iTunes 4.8 out yet? I’m running 4.7.1 and I just ran Software Update, but it doesn’t register an iTunes update yet. Anyway, it only makes sense to sync contacts via iTunes if you start thinking of it explicitly as management software for your iPod, I would think. In which case they should come up with a new name for it. This is the trouble with convergence, I guess: when features collide, software names often don’t make as much sense.
First of all, nice to see the remarks form back to its original … uhm, form.
It would be a lot easier if iSync supported brain synapses. All this data, all these devices, and only ONE source that knows what goes where — my head.
Seriously, I think you’re right on about being in transition. We’re definitely in the no-man’s zone of syncing. With that in mind, I’ve just concluded to trudge lightly and ALWAYS backup my contacts.
I couldn’t agree more Khoi; ever since Tiger came out, I haven’t really catched up to the syncing between my mini, Powerbook, iPod and phone. First of all I’m confused as to what purpose iSync has now, but also I seem to missync quite often. That never happened in Panther.
Syncing is a mess in the current Mac OS X. It all works just fine, but it’s spread all over the place the user experience is very poor. I believe iSync is being phased out. However, there are some very popular software apps (The Missing Sync comes to mind) that rely on it for integration with Apple’s apps.
WebDAV seems so perfect for data syncing. I wish Apple would provide a .Mac line tool for standard WebDAV servers — but that will never happen b/c it won’t net them any $$$. Oh well.
You skipped over my one big gripe about all this confusion. The menu bar iSync icon has ceased to work with anything other than .Mac. How does that make any sense? Obviously, if you have iSync open and sync with the menu bar icon, it works correctly. WTF?
They started to piss me off with the latest updates to Panther’s version of iSync because you used to be able to sync with just the menu bar icon, then iSync started to open up for no reason after a sync. Now in Tiger, it doesn’t even work anymore unless you have iSync open. How does that make any sense at all?
At least they made it sync faster, which was my other major complaint before. I always thought it was on account of bluetooth being slow and the computer having to figure out what was new and what was old.
I know this is probably aimed at allowing iSync to work with more phones than before…but…I feel I must add a rant…
In panther I could sync my 7650 easily and accuratly, in fact when I first got a mac I was incredably impressed at the simplicity of this, over the tedious and confusing method of syncing on a PC. You just pressed sync and it worked…
When I installed Tiger, it required me to add a small application to the phone to allow iSync to work. I then found out this ‘small’ application is over 400k, small in hard-disk terms but now takes up a sixth of the whole space on my phone(!) more than double the space of any other app…
This smells like very lazy programming from apple’s isync team…and is indicative of the other problems which are being encountered.
Ed’s right. It’s less about a period of transition and more about half-ass programming on Apple’s part. Palm has been the portable platform of choice for many, but to this day Palm devices synced through iSync do not translate iCal calendars to Palm’s Calendar categories and Address Book’s contact groups to Palm’s Contact categories. For some people, this makes iSync completely useless.
I’ve experienced similar shortcomings on other devices–I once had a phone which could, like many phones, associate multiple numbers under a single contact. For example, John Doe could have a home phone, a mobile phone, a fax, etc. iSync would create a new contact on the phone for each one of those.
I get reasonable functionality from Missing Sync, but it too relies on iSync for its Palm synchronization, and I can’t say MarkSpace’s customer support has been particularly impressive.
Mike Harper
Synching seems really piecemeal at this point in Tiger. I was planning on synching my phone and .mac with my laptop initially, so I started up iSync. After seeing that .mac is now synchronized through the System Preferences, I tried removing that .mac icon from iSync, but there’s no way to do so that I could see. Now there’s a useless icon sitting in iSync.
I went ahead and decided to sync with my phone, but iSync insisted on installing some sort of agent program on my phone (Nokia 6600). I’m fine with there being such a program, even if it stays running all the time (!) while wearing down my phone battery, but this wasn’t necessary under Panther — how come it is now?
Last week i heard that MS will release an Isync plugin for Entourage later this summer. Let’s hope this will solve some problems with third party tools. (e2sync does a good though)
I couldnt agree more. I just purchased a new iMac G5 to go along with my iBook G4 and I need some advice on how to keep stuff synced. I dont want to have to purchase .Mac if I dont have to. Are there some programs or techniques that anyone can recommend to keep Mail, iLife and all my files synced up?
I’ve also found iSync very disappointing – but maybe my expectations were a little off. When I first switched and got a PowerBook I saw a iSync in the Applications folder and thought, “Great, I’ll be able to move stuff between machines via my keydrive, much like the briefcase in Windows”.
Nope. It seems that sync’ing in this case was limited to specific data via a specific channel: a .mac account.
For all of Windows shortcomings I think the briefcase is a great little application. Easy to use synchronisation between any two folders, be they keydrives, network drives, or just two folders on the same box.
For all of the great software you get with OS X, why can’t there be a similar, all-purpose synchronisation tool?
A slightly happy ending to this story is that I managed to find a good third-party tool for this job called “Synk”. However, I still believe this sort of functionality should be standard in a modern operating system.
Martin Buis
Here’s the best syncing that I managed to get with my Treo: I run OSX2X to control my Windows box and sync to Outlook instead.
I tried sync in 10.3 and was so disappointed that I haven’t even bothered with 10.4. At one point isync was duplicating all my contacts, appointments etc, so I ended up with multiple thousands of these. I had to turn syncing off it got so bad.
Oh, I’m getting all annoyed just thinking about it again. The most un-Mac experience I’ve had from Apple.
Can I ask why you use both Entourage and Mail? I’ve used both in the past but switched to only Mail.app recently because I thought Tiger would offer better syncing possibilities than it now actually does.
Damien: Sure. I send all of my messages from Entourage and receive them in Mail, that way everything’s nice and tidy. Just kidding; actually I get all of my Subtraction email with Entourage and all of my Behavior email with Mail. In general, I prefer Entourage despite its less robust integration with the Mac OS X infrastructure; I’ve been getting Subtraction email with it for years. But I really like having two separate databases for my mail (though not my contacts, unfortunately), so when we started Behavior, I decided to use that program to deal with work-related messages.
Wow, no I hadn’t. I wasn’t even aware that it existed. It takes contacts from Entourage and makes them available to .Mac-friendly applications, is that right? I suppose it does the same thing as Paul Berkowitz’s Sync Entourage-Address Book AppleScript, though maybe with a bit more elegance.
yes exactly, its the most stable app out there (tiger coming up). there is a solution from pocketmac called gobetween but thats rather buggy.
as i said, microsoft will release an own isync plugin in a few months – but meanwhile e2sync does that all
what is going to happen is that they are going to kill isync, and bring you management of syncing through your itunes. think phones will be soon all ituned anyway once apple starts to OEM fairplay, thats where it is going….
Oh yes, Khoi, I had to write about iSync as well, right after I had upgraded to iTunes 4.8 and noticed that 2 out of my 3 “devices” told me they were now sync’d in some other application.
It seems the model for .Mac sync’ing has changed and now iSync is considered to be a .Mac API-enabled bridge for third-party devices, whereas the iPod is being centralized into iTunes. Not such a bad idea maybe, but that central point where everything is fired at the same time is lost, because when I sync my phone, I can see the menu icon for .Mac Sync spin, but when I select the menu icon any other time, it doesn’t branch out and start looking for my phone — it only syncs .Mac. So there may be a model, and it may make sense for Apple and API developers, but it *doesn’t make sense for users.*
And just a note about the iSync Agent: it has removed all the problems with P900 synching, (for me anyway) which was consistently horrible and only worked on the 4th try sometimes. So something good came out of this, I suppose.
Noah, that exactly what I was talking about. Although if you use the icon while iSync is open it will sync your phone. It makes not sense at all. This is one of the worst usability cases I’ve ever seen in my entire life.
Also, I sent them a feature request asking them to fix this back the way it was and for them to let me remove that stupid .Mac icon because the percentage of mac users actually “subscribing” to .Mac has got to be less than 50%.
mitsukai
So I have read lots of forums like this one trying to find a solution, and I seem to come to the conclusion that there is no way to do the same as with windows briefcase, without buying third-party software? There is nothing in OS X (any breed) that does it? Mac has been great, but I LOVE the sheer simplicity of windows briefcase (not to mention it being included in the OS) for making sure a copy of my work always sits on the network and my local drive and my USB-stick. I have a shortcut to my briefcase on the desktop and I simply right-click it, select “update all” and it hums away, checking versions of files etc, then brings up a little list of the changes available, at which point I can select files I want to skip being updated (if any) then click update and away it goes. Finished. There MUST be something for the Mac that does this?? Without .Mac??? I need waaay more space than a .Mac account provides, and I know I’m not the only one, not even including those who want a sync tool for their whole Home folder!!
For no good reason, I continually get my hopes raised up over the idea of clean, seamless synchronization across multiple databases and devices via my Macintosh. For example, I just want to be able to maintain a single store of contacts, at least, and have it reflected across all the various applications I use: Entourage and Apple Mail, iChat and Adium X, my mobile phone and my PDA if I ever use one again.
Khoi, not sure if you noticed the latest iTunes update, but version 4.8 now syncs your contacts/calendar for you instead of using iSync. This solves *one* of the many problems you mentioned…
(Also, it plays videos… one can only guess that it’ll soon sync them to your video iPod 😉 )
I hadn’t seen that. Is iTunes 4.8 out yet? I’m running 4.7.1 and I just ran Software Update, but it doesn’t register an iTunes update yet. Anyway, it only makes sense to sync contacts via iTunes if you start thinking of it explicitly as management software for your iPod, I would think. In which case they should come up with a new name for it. This is the trouble with convergence, I guess: when features collide, software names often don’t make as much sense.
First of all, nice to see the remarks form back to its original … uhm, form.
It would be a lot easier if iSync supported brain synapses. All this data, all these devices, and only ONE source that knows what goes where — my head.
Seriously, I think you’re right on about being in transition. We’re definitely in the no-man’s zone of syncing. With that in mind, I’ve just concluded to trudge lightly and ALWAYS backup my contacts.
I couldn’t agree more Khoi; ever since Tiger came out, I haven’t really catched up to the syncing between my mini, Powerbook, iPod and phone. First of all I’m confused as to what purpose iSync has now, but also I seem to missync quite often. That never happened in Panther.
I’m pretty new to this synching thing. So, what do you use to sync your contacts in Mail, iChat and bluetooth phone?
Syncing is a mess in the current Mac OS X. It all works just fine, but it’s spread all over the place the user experience is very poor. I believe iSync is being phased out. However, there are some very popular software apps (The Missing Sync comes to mind) that rely on it for integration with Apple’s apps.
WebDAV seems so perfect for data syncing. I wish Apple would provide a .Mac line tool for standard WebDAV servers — but that will never happen b/c it won’t net them any $$$. Oh well.
You skipped over my one big gripe about all this confusion. The menu bar iSync icon has ceased to work with anything other than .Mac. How does that make any sense? Obviously, if you have iSync open and sync with the menu bar icon, it works correctly. WTF?
They started to piss me off with the latest updates to Panther’s version of iSync because you used to be able to sync with just the menu bar icon, then iSync started to open up for no reason after a sync. Now in Tiger, it doesn’t even work anymore unless you have iSync open. How does that make any sense at all?
At least they made it sync faster, which was my other major complaint before. I always thought it was on account of bluetooth being slow and the computer having to figure out what was new and what was old.
I know this is probably aimed at allowing iSync to work with more phones than before…but…I feel I must add a rant…
In panther I could sync my 7650 easily and accuratly, in fact when I first got a mac I was incredably impressed at the simplicity of this, over the tedious and confusing method of syncing on a PC. You just pressed sync and it worked…
When I installed Tiger, it required me to add a small application to the phone to allow iSync to work. I then found out this ‘small’ application is over 400k, small in hard-disk terms but now takes up a sixth of the whole space on my phone(!) more than double the space of any other app…
This smells like very lazy programming from apple’s isync team…and is indicative of the other problems which are being encountered.
Ed’s right. It’s less about a period of transition and more about half-ass programming on Apple’s part. Palm has been the portable platform of choice for many, but to this day Palm devices synced through iSync do not translate iCal calendars to Palm’s Calendar categories and Address Book’s contact groups to Palm’s Contact categories. For some people, this makes iSync completely useless.
I’ve experienced similar shortcomings on other devices–I once had a phone which could, like many phones, associate multiple numbers under a single contact. For example, John Doe could have a home phone, a mobile phone, a fax, etc. iSync would create a new contact on the phone for each one of those.
I get reasonable functionality from Missing Sync, but it too relies on iSync for its Palm synchronization, and I can’t say MarkSpace’s customer support has been particularly impressive.
Synching seems really piecemeal at this point in Tiger. I was planning on synching my phone and .mac with my laptop initially, so I started up iSync. After seeing that .mac is now synchronized through the System Preferences, I tried removing that .mac icon from iSync, but there’s no way to do so that I could see. Now there’s a useless icon sitting in iSync.
I went ahead and decided to sync with my phone, but iSync insisted on installing some sort of agent program on my phone (Nokia 6600). I’m fine with there being such a program, even if it stays running all the time (!) while wearing down my phone battery, but this wasn’t necessary under Panther — how come it is now?
Last week i heard that MS will release an Isync plugin for Entourage later this summer. Let’s hope this will solve some problems with third party tools. (e2sync does a good though)
I couldnt agree more. I just purchased a new iMac G5 to go along with my iBook G4 and I need some advice on how to keep stuff synced. I dont want to have to purchase .Mac if I dont have to. Are there some programs or techniques that anyone can recommend to keep Mail, iLife and all my files synced up?
I’ve also found iSync very disappointing – but maybe my expectations were a little off. When I first switched and got a PowerBook I saw a iSync in the Applications folder and thought, “Great, I’ll be able to move stuff between machines via my keydrive, much like the briefcase in Windows”.
Nope. It seems that sync’ing in this case was limited to specific data via a specific channel: a .mac account.
For all of Windows shortcomings I think the briefcase is a great little application. Easy to use synchronisation between any two folders, be they keydrives, network drives, or just two folders on the same box.
For all of the great software you get with OS X, why can’t there be a similar, all-purpose synchronisation tool?
A slightly happy ending to this story is that I managed to find a good third-party tool for this job called “Synk”. However, I still believe this sort of functionality should be standard in a modern operating system.
Here’s the best syncing that I managed to get with my Treo: I run OSX2X to control my Windows box and sync to Outlook instead.
I tried sync in 10.3 and was so disappointed that I haven’t even bothered with 10.4. At one point isync was duplicating all my contacts, appointments etc, so I ended up with multiple thousands of these. I had to turn syncing off it got so bad.
Oh, I’m getting all annoyed just thinking about it again. The most un-Mac experience I’ve had from Apple.
for win-briefcase like file synching go this way:
http://www.softobe.com/products/flsy/pp.html
Khoi,
Can I ask why you use both Entourage and Mail? I’ve used both in the past but switched to only Mail.app recently because I thought Tiger would offer better syncing possibilities than it now actually does.
Damien: Sure. I send all of my messages from Entourage and receive them in Mail, that way everything’s nice and tidy. Just kidding; actually I get all of my Subtraction email with Entourage and all of my Behavior email with Mail. In general, I prefer Entourage despite its less robust integration with the Mac OS X infrastructure; I’ve been getting Subtraction email with it for years. But I really like having two separate databases for my mail (though not my contacts, unfortunately), so when we started Behavior, I decided to use that program to deal with work-related messages.
khoi, every tried e2sync.com?
i use entourage/exchange for my biz and mail.app for private mails while synching entourage and mail/mac os contacts with this tool
Wow, no I hadn’t. I wasn’t even aware that it existed. It takes contacts from Entourage and makes them available to .Mac-friendly applications, is that right? I suppose it does the same thing as Paul Berkowitz’s Sync Entourage-Address Book AppleScript, though maybe with a bit more elegance.
yes exactly, its the most stable app out there (tiger coming up). there is a solution from pocketmac called gobetween but thats rather buggy.
as i said, microsoft will release an own isync plugin in a few months – but meanwhile e2sync does that all
forgot to say that it could synch calendar and todo items as well, but ical… you know…
and another thing: the problem of synching entourage contacts to my razr v3 is solved by the same way
what is going to happen is that they are going to kill isync, and bring you management of syncing through your itunes. think phones will be soon all ituned anyway once apple starts to OEM fairplay, thats where it is going….
Oh yes, Khoi, I had to write about iSync as well, right after I had upgraded to iTunes 4.8 and noticed that 2 out of my 3 “devices” told me they were now sync’d in some other application.
It seems the model for .Mac sync’ing has changed and now iSync is considered to be a .Mac API-enabled bridge for third-party devices, whereas the iPod is being centralized into iTunes. Not such a bad idea maybe, but that central point where everything is fired at the same time is lost, because when I sync my phone, I can see the menu icon for .Mac Sync spin, but when I select the menu icon any other time, it doesn’t branch out and start looking for my phone — it only syncs .Mac. So there may be a model, and it may make sense for Apple and API developers, but it *doesn’t make sense for users.*
And just a note about the iSync Agent: it has removed all the problems with P900 synching, (for me anyway) which was consistently horrible and only worked on the 4th try sometimes. So something good came out of this, I suppose.
Noah, that exactly what I was talking about. Although if you use the icon while iSync is open it will sync your phone. It makes not sense at all. This is one of the worst usability cases I’ve ever seen in my entire life.
Also, I sent them a feature request asking them to fix this back the way it was and for them to let me remove that stupid .Mac icon because the percentage of mac users actually “subscribing” to .Mac has got to be less than 50%.
So I have read lots of forums like this one trying to find a solution, and I seem to come to the conclusion that there is no way to do the same as with windows briefcase, without buying third-party software? There is nothing in OS X (any breed) that does it? Mac has been great, but I LOVE the sheer simplicity of windows briefcase (not to mention it being included in the OS) for making sure a copy of my work always sits on the network and my local drive and my USB-stick. I have a shortcut to my briefcase on the desktop and I simply right-click it, select “update all” and it hums away, checking versions of files etc, then brings up a little list of the changes available, at which point I can select files I want to skip being updated (if any) then click update and away it goes. Finished. There MUST be something for the Mac that does this?? Without .Mac??? I need waaay more space than a .Mac account provides, and I know I’m not the only one, not even including those who want a sync tool for their whole Home folder!!