TUAW reader Jamie Phelps has possibly stumbled upon a nasty iPhone synching bug when keeping one's iTunes library on an external hard drive. While tips like our how-tos for setting up iTunes with external drives or even an AirPort Disk work pretty well even when synching iPods with them, Jamie found that his iPhone gets the brainwash treatment when he's away from the drive containing his external iTunes library. As the story goes, Jamie synched his iPhone with a few songs and playlists, made a couple new playlists and then synched again. Hitting the road, however, and getting away from his external iTunes library drive is when the bug rears its nasty head: plugging the iPhone in while on the go caused iTunes to wipe out the new playlists and songs from the second sync operation, basically reverting them to their state before the second sync. To verify, Jamie even got adventurous and tried this whole thing a second time, once again watching iTunes blow away changes from the previous iPhone sync when the external media library isn't mounted.

This is the first time I've heard of iTunes handling this kind of setup in a poor way; for as long as I can remember, iTunes has been clever enough to realize what's happening and and would either not sync anything to an iPod when away from the library drive, or it would actually sync any media downloaded or imported while away (as we've mentioned before, you can use the Advanced > Consolidate Library command to move all this new media once reconnected with the library drive). Since we don't really have any evidence of Apple deliberately changing this behavior for their iPods or iPhones, it makes sense for this quirk to be classified as a bug that will hopefully be squashed with an inevitable iPhone software update. But what say you, TUAW readers? Anyone else get bit? Sound off.

As its name suggests, FacebookSync is a tiny freeware app from FSB Software that - wait for it - syncs your friends' info from Facebook to Mac OS X's Address Book. Upon running it, a window much like the one you see above will appear for every contact that either doesn't have an Address Book entry at all, or is missing information that could be pulled down from Facebook. It can even pull down images in case your Address Book contacts don't have those either, which is handy since apps like Mail, iChat, Growl + Gmail and Adium can use these pics to help identify these contacts.

Whilst trying this out, FacebookSync seems to work pretty well, though I admittedly don't spend much time on it and I only have a dozen or so friends. Still, it added the information I told it to (and for the record, I'm on 10.4.9 and have over 450 contacts in Address Book already), so I'll give it two thumbs up. Before running FacebookSync, however, I highly recommend you chose File > Backup Address Book in Address Book to create a clean, recent copy in case things go south. FacebookSync isn't likely to eat your cat or cause your Apple TV to implode, but having a Plan B is an absolute must when playing with software like this.

[via digg]

Spanning Sync looks to be the holy grail of true, two-way calendar synchronization between Apple's iCal and Google Calendar. Yes: by 'two-way' I mean 'you can edit the same calendar in either place and the changes will synchronize.' Nasty translation I know, so maybe you should go watch their demo video to really get your mouth watering. In it, one of Spanning Sync's creators shows off how easy it is to link iCal calendars with equivalents in Google Calendar (bonus points for the ability to chose exactly which calendars shake hands), as well as moving an event in one calendar and having the change sync to the other. If this doesn't have you excited, please excuse me while I go check my blood pressure.

Spanning Sync's blog has more details, and its release is billed as 'coming soon.' Stay tuned to TUAW as well, as I was fortunate enough to get my name in on the private beta before the signup list closed, and I'll have a screencast and a review for you as soon as possible.

Our friends over at Download Squad reviewed Calgoo, an offline Google Calendar client, last month. The reason we didn't pick it up is simply because it didn't run on Mac OS X at the time. Recently that changed, so here we go - but it is very apparent why they call this a first draft (as opposed to 'beta' or even 'pre-alpha').

Calgoo appears to be a Java app, or at least need it for something under the hood, and as you can see: it isn't quite on the Mac OS X side of the GUI fence. For some odd reason, users must register at Calgoo's site (which I begrudgingly did in the name of blogging) in order to be able to download and actually use the app. The actual setup is pretty straight forward, and syncing seemed to run well (a 'Message Log' tab in the upper right lets you keep an eye on activity), but navigating Calgoo's UI is anything but intuitive. Like Jason at Download Squad, I too couldn't see any of my appointments until I figured out their obscure calendar list in the lower left corner (hint: you can select and view individual calendars, or click at the top of the list to view them all. Why it's an actual process to get even any of your calendars to appear is anyone's guess). There are various other quirks and perks, such as Calgoo running on Mac, PC and Linux, event tagging/filtering and the fact that it downloads your Gmail buddies for easy attendance listing, but I was happy to see what is perhaps the most significant feature of Calgoo work like a charm: syncing with Google Calendar. I created a couple basic events in Calgoo and one in gCal, then synced. Once the dust settled, everything was reassuringly in order across both places, so at least that's a good selling point at this 'first draft' stage - cuz that UI sure won't be winning any Apple Design Awards anytime soon.

So would I recommend Calgoo? Yes and no. If you're just gaga for gCal, sure - it seems like a decent client, but there's definitely a UI learning curve. However, this seems to be the only app I've seen that has put a good foot forward in accomplishing such a task as truly synchronizing with Google Calendar, so I'll tip my hat to Calgoo and hope to see what tidings its evolution brings.

Mark/Space, purveyors of popular Missing Sync middle-man software that lets more than just iSync-friendly devices shake hands with your Mac, has just announced yet another version in their lineup: Missing Sync 1.0 for the PSP. In addition to all those games, movies and music files you're lugging around with Sony's hot little gaming machine, you can now synchronize Address Book, iCal events and tasks, notes (with their included Notebook app), WebSnacks™ (a website downloader that can include RSS feeds for offline viewing), iPhoto albums, iTunes playlists, game backups, and even track content across multiple memory sticks. To top it all off: Mark/Space even included a Universal Binary video encoder if all those other goodies are already boring you.

If all of this has your PSP thumbs 'a tappin' and you're ready to download a demo, you might be disappointed by a Mark/Space tradition that's always irked me: as far as I can tell, no demo is available; you either have to take the plunge and drop the $29.95 for a license, or gaze at the product page from afar, never to open a Missing Sync for PSP .DMG file of your very own.

iPod.iTunes offers 8 different ways of synchronizing your iTunes library and playlists between both devices, giving you powerful control over what files are moved where and how. All formats are supported, including MP3, AAC, protected AAC (iTMS purchases), Audible books, and video files. PC-formatted iPods are compatible, and all metadata such as your song ratings, play count and album art are preserved in the transfer. This is a great utility for anyone in need of an easy method to clone an iPod, keep iTunes libraries on different Macs in sync or simply back up your iPod's library if it's the only place you keep all your media (Apple sadly doesn't provide a way of doing this).

Check out the full list of features of everything iPod.iTunes is capable of. Another handy trick this app performs is that it can live and run directly from your iPod, in which case your registration ($35 USD) travels with you. A demo is available from crispSofties.

Today's "what were you thinking, Apple?" is brought to you by the .Mac System Preference pane, iSync and that "Sync Services wants to sync more than X% of your items" popup window.

In case you can't figure out the silliness that is the image I've included with this post (and I don't blame you), it's a combination of the .Mac System Preference Pane (on left), the .Mac tab of iSync (bottom right), and iSync's preferences that allow me to chose the Data Change Alert percentage threshold (top left).

I recently added about 200 notes to Yojimbo on my iMac that I exported out of an old copy of StickyBrain a while ago. On my PowerBook, this obviously triggered the .Mac Sync warning of "you're about to change more than 5% of your data, are you sure you want to do this?" dialog. I then thought to myself: "hmm, since I change a lot of my .Mac stuff on a regular basis, maybe I should increase that percentage so this dialog doesn't bother me again."

I haven't done this in a while, but since I came up through Jaguar and Panther I was used to tweaking .Mac stuff in iSync. So I strolled on over to the .Mac tab in iSync to - oh but wait! As you can see in the bottom right of my screenshot, it sounds like iSync is no longer used to manage .Mac information. Woops, my mistake. Maybe I should open up the .Mac System Preference pane to - wait a minute... I don't see any place in that preference pane to tweak the Data Change Alert setting!

By now you probably get where I'm going with this, so I'll just leave you with a question: how on earth did this happen, Apple? With Tiger, you said that you unified and improved the .Mac user experience... by sending me to three different locations and preference systems to get this figured out?

Here's hoping Leopard brings with it the Mac-daddy (haha) of updates to one of your most-pimped features of OS X.