Problems syncing photos with iPod, iPhone, or Apple TV and iPhoto 8.1
Posted on December 8, 2009 by Brian Webster
Filed Under Tips & Tricks, iPhoto, iPhoto Library Manager, iTunes | 4 Comments
A bug has recently cropped up in iPhoto (version 8.1 appears to be the first version with the bug, and the bug remains as of version 8.1.1) which can cause problems when attempting to sync your photos using iTunes to any device, such as an iPod, iPhone, or Apple TV. I’ve seen a whole bunch of reports of iPhoto Library Manager users encountering this bug, enough that I thought a blog post describing the problem and the solution would be helpful.
Symptoms
If you suffer from this bug, when you open iTunes and attempt to sync a device with your iPhoto library via iTunes, you’ll get an error reading “iTunes cannot sync photos to (whatever device you’re using) because of a problem on your computer. An unknown error occurred (-50)”.

When using iPhoto Library Manager to try to look at an affected library’s contents, you’ll get an error message reading “The album data file for this library is malformed. Encountered unknown ampersand-escape sequence at line X”.

Cause
The root cause of this problem is triggered by the following setup:
- You’ve created a custom slideshow in your iPhoto library
- You have used the “Music” button in iPhoto to assign a track from iTunes to play while the slideshow is being displayed
- The track you chose has an ampersand (&) character anywhere in the name of the song, the song’s artist name, or the song’s album name.
It’s actually the path to the song that’s relevant, but since iTunes organizes your music into subfolders based on these three fields, an ampersand existing in any one of them will result in the file’s path having an ampersand in it. An example is illustrated below, where a song by “Rob Thomas & Santana” is selected as the music for a slideshow

Solution
There are actually a couple different ways to work around this problem. I’ll list them here in order from simplest to most complicated.
- Delete the slideshow. Simple, but effective. But on the other hand, you lose your slideshow!
- Turn off music for the slideshow. Uncheck the “Play music during slideshow” checkbox and then click the “Apply” button to save your changes. But what if you still want to have music during your slideshow…?
- Choose a different song. Select a different song, one where no ampersand character occurs in either the song name, artist, or album title, then click “Apply”. But what if you really really want that specific song you spent hours and hours choosing from your vast music collection to find the perfect one?
- Remove all the ampersands. The only way to keep using the same song will be to remove any offending ampersands that occur in the path to the song file. For this, you’ll have to open up iTunes, find the song in question, and change the name, album, and/or artist to remove any ampersand characters in those fields. After you’ve done so, you’ll also need to go back into iPhoto and re-choose the song in the slideshow music settings, to make sure iPhoto is updated to point to the song’s new location.
One additional source of ampersands is if your entire media folder is located inside a folder or drive with an ampersand in the name. For example, if you store your iTunes media folder on an external hard drive and have named the drive “Music & Video”, then this will cause all your songs to have an ampersand character in their path. If this is the case, then you’ll need to rename the hard drive or folder to remove the ampersand.
Once you’ve done that, if you quit iPhoto, open up iTunes, and try syncing your device again, you should now be able to successfully sync your photos. If you still get an error, double check and make sure that the changes you made in iPhoto have “stuck” (click that “Apply” button!), and if you have multiple slideshows, that you’ve checked all of them for potential troublemaking music settings.
iPhoto Library Manager 3.5 public beta
Posted on March 11, 2009 by Brian Webster
Filed Under News, Updates, iPhoto, iPhoto Library Manager | 1 Comment
Work on iPhoto Library Manager 3.5 has been progressing well, and things are now to the point where the major new features are up and running. However, given the relative complexity of the new features (especially transferring faces data between libraries), I’ve decided to do a (hopefully brief) public beta of iPLM 3.5, so I can get it tested out on a wide variety of setups and make sure to get all the kinks worked out.
The main additions are, of course, the ability to copy Places and Faces data from one library to another when copying photos under iPhoto ‘09. This includes both copying individual albums/events and merging libraries. There are also several other changes and bug fixes included in the release (full release notes are at the bottom of this post).
This is pre-release software – I’ve tested things as thoroughly as possible, and there are no known bugs in the beta, but there is still the possibility of issues popping up, especially when dealing with library setups I haven’t been able to test myself. I strongly recommend backing up your iPhoto libraries before doing any major photo copying.
So, if you have iPhoto ‘09 and want to try out copying photos between your libraries while keeping your Places and Faces intact, you can download the public beta here. Note that I haven’t yet done my full suite of tests on earlier versions of iPhoto, and there isn’t really much in the way of new features for those earlier versions, so if you haven’t upgraded to iPhoto ‘09, there’s probably not much point in downloading the beta.
The system requirements are the same as 3.4.5, and you still need a registered copy in order to perform advanced features such as photo copying and merging. I will be posting updates as bugs get reported and things get fixed – you can use the “Check For Updates” menu item from within the program to check for and install any new updates. If any issues arise, please contact support@fatcatsoftware.com.
Update 4/3/09: Things have been progressing well, and iPLM 3.5 is getting close to completion. There are still a couple issues that need working out, but nothing major at the moment. I’ve just posted a new beta, 3.5b5, that is now available for download. Due to a mistake in 3.5b4, the “Check For Updates” menu item will not detect this new version if you have 3.5b4 currently installed, so you will have to download it manually instead from the link above.
Changes in iPhoto Library Manager 3.5 public beta
- When the user clicks the Cancel button, we now present a dialog to verify that they do in fact want to cancel the operation
- Removed the preference for relaunching iPhoto during a merge. This pref was for working around a bug in iPhoto 6, so we now just relaunch automatically when merging with iPhoto 6.
- Removed the preference setting for double clicking a library – double click now always opens the library in iPhoto, and a single click renames the library
- iPhoto Library Manager now creates its own log file and logs progress and error information as it copies photos (accessible from the Window menu)
- Photos that were published to a MobileMe gallery are now always included in the main library during a merge, and not just in the gallery itself
- Fixed a problem where movies and original versions of photos would not be copied for some users
- Tagged faces are now transferred along with photos that are copied/merged between libraries in iPhoto ‘09
- Places data is now copied along with photos when performing a copy or a merge in iPhoto ‘09
- Added a “selection” property to the Applescript dictionary so scripters can access the currently selected library
iPhoto ‘09 + Safari 4 beta + geotags = crash
Posted on March 3, 2009 by Brian Webster
Filed Under iPhoto | Comments Off
Update 3/20/09: it appears that this crasher has been resolved as of iPhoto 8.0.1, so if you’re encountering this problem, make sure to update to the latest version of iPhoto using Software Update.
Just as a public service announcement, I thought I’d post about a conflict between iPhoto ‘09 and the Safari 4 beta that could cause some rather mysterious looking crashes, regardless of whether you use iPhoto Library Manager. The crash occurs when importing photos into iPhoto, but only under certain, somewhat odd conditions. The crash occurs when:
- You have both iPhoto ‘09 (version 8.0) and the Safari 4 beta installed on your machine
- You’re importing a batch of photos into iPhoto, at least one of which has embedded geotagging data
- This is the first import that you have done since launching iPhoto. If you first import a batch of photos with no geotags, then do a second import that does include geotags, it will not cause a crash
If you’ve been experiencing weird crashes when importing photos and have this affecting you, the easy solution is to uninstall Safari 4 and go back to using Safari 3. If you really don’t want to uninstall, you can also always remember to import a non geotagged photo before doing your geotagged photos (good luck with remembering that
).
iPhoto ‘09 initial compatibility report
Posted on January 27, 2009 by Brian Webster
Filed Under News, iPhoto, iPhoto Library Manager | 11 Comments
Well, I’ve had a chance to try out iPhoto ‘09 for a couple hours now, and here are the notes I have so far regarding compatibility with iPhoto Library Manager:
- Viewing and switching between existing libraries works fine. iPhoto will prompt you to upgrade your library to the new version when you first open a particular library. Note that after you upgrade a library, you will no longer be able to open it in earlier versions of iPhoto.
- New libraries created using the current version of iPhoto Library Manager won’t work the first time you open them in iPhoto. For now, hold down the option key while opening iPhoto and use its interface to create a new library if you need to create one. You can then use the “Add Library” button in iPhoto Library Manager to add the library to iPLM’s library list, after which you can use the library normally. This will be fixed in the upcoming iPLM update.
- As expected, advanced functions such as copying albums between libraries and merging do not work and will produce an error message. Rebuilding a library will also not work, although the “Extract Photos” function should still work OK. Trying to use these features won’t result in any harm, they just won’t work. Again, these issues will be fixed in the upcoming iPLM update.
- iPod Folders appear to work with no problems with iPhoto ‘09
So, that’s what I have for now, I’ll be continuing to test things out and will post any updates on this page. I’ll then be starting work on updating iPLM to fix any of the issues that come up with iPhoto ‘09. That will be a free update for all users, so if you have purchased or plan on purchasing a copy of iPLM, you will be able to update for free when it is available.
Update 1/30/09: I’ve had a chance to work with iPhoto ‘09 for a couple days now, and here’s what I’m planning on doing. Two of the big new additions to iPhoto ‘09 are the new Faces and Places features. These features attach new types of metadata to your photos to identify people in the photos and where the photos were taken. It would obviously be very nice to be able to transfer from library to library when copying albums or performing merges. It looks like this is feasible, but it also looks like it will take a fair bit of work and time to accomplish.
So, what I think I’m going to do is to get out a quick 3.4.4 update for iPLM that gets things running under iPhoto ‘09 with the same capabilities as the current version. So, you’ll be able to copy albums, merge libraries, etc. but this first update will not handle any of the new Faces/Places data. The update will basically be to get people back up and running so they can use iPLM with iPhoto ‘09, fixing various issues such as the library creation bug mentioned above, etc. and should hopefully be available sometime next week.
Then, after that’s out, I’ll start in on getting Faces/Places integration working, and once that’s done, there will be a separate 3.5 update that will include that new, iPhoto ‘09 specific functionality. That will probably take a little longer, but it should be doable. If you have photo copying or merging you want to do but want to upgrade to iPhoto ‘09 right away, I would recommend doing any photo copying/merging you want before doing the iPhoto upgrade. That way, you can get your libraries straightened out, and then go ahead and assign faces/places in the upgraded library. If you assign faces/places and then do your copying/merging, you won’t be able to do so while retaining the face/place data until iPLM 3.5 comes out.
iPhoto Library Manager and iPhoto ‘09
Posted on January 6, 2009 by Brian Webster
Filed Under Apple, News, Updates, iPhoto, iPhoto Library Manager | 7 Comments
As many of you know, today Apple announced a new update to their iLife suite, iLife ‘09, which includes an update to iPhoto. iPhoto ‘09 won’t be available until the end of January, but I’d like to fill you in on the status of iPhoto Library Manager compatibility with this new version of iPhoto.
I don’t get special early releases of iPhoto or anything like that, so I’ll be working with it for the first time once I can pick up a copy from Apple. In the past, major iPhoto updates have required updating iPhoto Library manager to provide full compatibility for all its features, and I suspect things will be the same this time around. The basic functionality of iPLM (creating new libraries and switching back and forth between them) has never broken in any previous iPhoto update, so I’m pretty sure that stuff will be the same this time around. The more advanced features, such as copying albums between libraries and merging libraries together, however, require a bit more work to make sure they work properly. For iPhoto ‘07 and iPhoto ‘06, it has taken me about two weeks each time to issue an iPLM update for the new version of iPhoto, so it will hopefully take approximately the same amount of time this time around.
What I can tell you is that the update will be a free update for any existing users of iPhoto Library Manager, so if you buy a copy now, rest assured you will be able to use it with iPhoto ‘09 once the update is released. For those of you wondering whether to upgrade to iPhoto ‘09, you should still be able to switch between your libraries fine after updating, but you almost certainly won’t be able to do any photo copying or merging until the iPLM update is ready. If you really need to be able to use iPLM to do photo transfers, I would recommend holding off upgrading iPhoto until the update to iPhoto Library Manager is ready.
My thanks in advance for your patience, I will be posting further updates on how things are going as I learn more about what needs to be done for the update.
How to create a fake digital camera for Image Capture
Posted on December 5, 2008 by Brian Webster
Filed Under Development, iPhoto | 1 Comment
I’ve been fooling around with some Image Capture APIs lately, but the only convenient camera device I have to work with is my iPhone, which doesn’t really have any way to put specific images onto it if I want to test things out like different formats, movies, etc. After digging around with the Image Capture SDK a bit, though, I’ve found a simple way to make a fake “camera” that Image Capture will recognize, but doesn’t require plugging in a physical device.
The trick is to create a disk image that, when mounted, Image Capture believes to be a digital memory card, and treats as a digital camera, so it shows up in iPhoto, Image Capture.app, and so forth. There appear to be a bunch of different ways to do this, but here’s the method I used that worked for me:
- Open Disk Utility and click the “New Image” button in the toolbar. In the configuration sheet, choose “MS-DOS (FAT)” for the Volume Format, and “Single Partition – Master Boot Record Partition Map” for the Partitions setting. You can enter whatever name and volume size you like, then click “Create”.
- Once the image is created and mounted, open it up in the Finder. Create a new folder at the root level of the mounted disk image and name it “CAMERA”. Then, go ahead and copy whatever pictures or other items you want to test with inside the CAMERA folder. This appears to be one particular camera’s way of storing photos on its memory card – there are a whole bunch of others (”DCIM”, “Photos”, “Videos”, etc.) that would work equally well.
- Click the eject button in the Finder, then double click the image file to mount the image again. If everything is set up correctly, the act of mounting the image should cause Image Capture to fire up whatever application you have set to handle your digital cameras (e.g. iPhoto), and the images you put in the CAMERA folder should appear in the list of photos for the device.
Not only does this save having to plug and unplug a device whenever you’re doing testing with Image Capture, but it’s also really nice for test suites, since you can just include the disk image as data for your tests, and then mount the image to simulate plugging in a camera.
Disappearing iPhoto libraries on external drives
Posted on May 16, 2008 by Brian Webster
Filed Under Tips & Tricks, iPhoto, iPhoto Library Manager | 1 Comment
I just came across this article on TidBITS explaining how to deal with stray “doppleganger” folders that get created in the /Volumes directory, where external hard drives and network drives are mounted by Mac OS X. I’ve seen this particular issue come up quite a number of times with people working with iPhoto, so I’m glad to see someone else writing on the topic. I encourage everyone to go read the article, since you never know when this will crop up on your machine, and it’s good to have this floating around in your head as a possible cause.
The way this typically affects people using iPhoto is when you’re trying to open a library that you store on an external hard drive. One day, for no apparent reason, you open up iPhoto and are greeted with a totally empty library. Where did all my photos go!? Aaaaagh!
You’ll be glad to know that your photos aren’t actually gone, they’re just in a slightly different place, so iPhoto can’t find them. iPhoto stores its library location by a plain path, so it will be pointing to the “doppleganger” folder, instead of following the library to its new path where the external drive is actually located.
iPhoto Library Manager itself uses aliases to track library locations, so when this happens, it will usually figure out to update itself to point to libraries’ new locations. If it doesn’t automatically update, all you have to do then is to re-add any libraries that are pointing to the wrong place to iPLM’s library list, either by using the “Add Library” button, or by just dragging each library into the list. You can then remove the old, stale references from the library list, and you should be all set. If you’re just using iPhoto’s option-key-on-startup trick to switch libraries, you can just do that and go find the real library on the external drive to get iPhoto pointed back to the correct location.
iPhoto 7 editing behavior
Posted on October 9, 2007 by Brian Webster
Filed Under Tips & Tricks, iPhoto, iPhoto Library Manager | 1 Comment
While fiddling around with the editing controls in iPhoto 7, I came across a small bit of new behavior that I thought may be interesting to some. If you use any of the sliders in the “Adjust” palette, iPhoto 7 will actually remember the positions of those sliders if you come back to that photo to edit it a second time.
Picture after editing and reopening
This is in contrast to iPhoto 6, where opening this photo back up again would result in the “Temperature” slider being reset to 0. This is pretty cool overall, even if it prevents you from doing X-TREME 200% SHARPNESS adjustments by sliding the slider to 100% twice.
However, if you choose to edit your photo with an external editor, such as Photoshop or Preview, iPhoto will not remember these slider settings.
Picture after editing in Preview
Also note that when copying photos with iPhoto Library Manager, transferring both the original and modified versions of the photo does the equivalent of editing in an external editor, so the slider settings won’t be transferred.
iPhoto Library Manager 3.3 released
Posted on August 20, 2007 by Brian Webster
Filed Under News, Updates, iPhoto, iPhoto Library Manager | 5 Comments
I’m pleased to announce that iPhoto Library Manager 3.3 is shipping today, with full support for iPhoto 7! (On a terminology note, I’ve decided I’m going to at least try referring to this new iPhoto as “iPhoto 7″ and not “iPhoto ‘08″. All of Apple’s docs seem to use the ‘08 nomenclature, but trying to use it myself, it just sounds/looks really weird, so I’m going to stick with “iPhoto 7″ unless it causes mass confusion and riots.)
The update is free for all users and can be downloaded from the main iPLM page. iPhoto 7 support is the major feature of this release, so functionally speaking it’s mostly the same as 3.2.6, with a couple of notable exceptions.
- The first good news is that, as a result of changes in iPhoto 7, album hierarchies can now be preserved when copying between libraries! This has been something I’ve wanted to do for a while, but just wasn’t able to in previous versions, so for iPhoto 7 users, that will be nice to have.
- I’ve made the look of the album list mimic the look of the iPhoto 7 album list, including the background color and separate sections with titles (you can click here to see how it looks). Older libraries will still be displayed with the plain look.
- Unlike in iPhoto 6, the list of events (formerly known as rolls) can now be sorted by their date in the iPhoto Library Manager window. This makes it somewhat easier to track down a particular event you’re looking to copy to another library.
So, there it is! I’ve of course tested the bejeezus out of it, but if anyone has issues that crop up, drop me a line at support@fatcatsoftware.com.
iPhoto 7/’08 observations
Posted on August 9, 2007 by Brian Webster
Filed Under Development, iPhoto, iPhoto Library Manager | 14 Comments
I’ve only been playing around with iPhoto 7 for a little bit now, but I’ve found some interesting nuggets on how things have changed in comparison to iPhoto 6. And yes, the official version number for the new iPhoto is 7, even thought it’s part of iLife ‘08. Thanks for not making things totally confusing, Apple. *sigh*
Events are the new Rolls
As I suspected might be the case, it appears that the new Events feature in iPhoto 7 is, structurally speaking, a rebranded use of Rolls from iPhoto 6 and earlier. In fact, I don’t see the term “roll” used anywhere in the iPhoto 7 interface anymore. I’m happy with the new Events interface, as it is a marked improvement and much more useful than rolls were under iPhoto 6. At the core of things, they basically work the same, but there are a couple important differences in behavior.
Like rolls, events are mutually exclusive, so every photo belongs to a single event, no more, no less. However, in iPhoto 6, every distinct import was grouped into a single roll. In iPhoto 7, a single import can now result in multiple events, depending on what settings you have in the preferences, and the dates of the photos that were taken.
Library folders are now packages
In previous versions of iPhoto, your library folder was just that, a folder. It appeared as a normal folder in the Finder, and you could dig through it and mess with things just as easily as any other folder. In iPhoto 7, Apple has decided to make iPhoto folders into packages instead. A package is simply a folder that doesn’t appear as a folder in the Finder. Most applications are actually packages (or rather, a special type of package called a bundle), and many other things, from plugins to documents are also marked as packages. You can still see what’s inside a package by control-clicking it in the Finder and selecting “Show Package Contents”.
This may cause a little terminology confusion in the short run, as the term “iPhoto library folder” is used fairly pervasively, but I think in the long run this is a good move by Apple. Countless people have unknowingly borked their iPhoto libraries in various ways by moving stuff around inside the library folder. This is actually not unreasonable behavior, but iPhoto reacts very poorly to having its library messed around with. So, my basic reaction is, “What took them so long?”.
For those curious in the technical details, iPhoto libraries don’t require an extension, as is the norm for most applications that store their data in packages, but instead have their “Is Package” bit set so that the Finder displays it as a package, even without an extension. It also sets the type/creator on the folder so that the library is displayed as a pretty icon in the Finder, as well as a Contents/PkgInfo file containing the same information.
Auto import folder
I don’t see this mentioned anywhere in the documentation, but there is now a new folder inside the library named “Auto Import”. It appears that how this works is, if you put some photos into the Auto Import folder, then the next time you launch iPhoto, it will look in that folder and import any photos it finds there. It does delete any photos in that folder after importing them. There is also an “auto import” Applescript command, but calling it doesn’t seem to do anything, at least not as far as I can see. I have a feeling this may have been a feature that was pulled out late in development, and they just forgot to remove the Applescript command and the actual folder inside the library.
New keyword interface
Another iPhoto release, another new interface for assigning keywords. By my count, this is at least the 4th different interface iteration for this feature in iPhoto. I also think this is the first time that the new interface has actually been an improvement over the old one.

In iPhoto 7, you can actually edit keywords directly inside the main viewer. This is quite cool, as it will autocomplete existing keywords as you type, and if you type a new keyword and type a comma, it will automatically create a new keyword with what you typed. This is a vast improvement over iPhoto 6, where you had to go into the preferences window just to add new keywords to your list.
But how do you edit the keywords of multiple photos at a time? This actually took me a good while to find, as the info window no longer contains a tab for editing keywords as it did before, and the keywords pane/button no longer exists down in the lower left corner of the window. I eventually found it, under the Window menu, there is a “Show Keywords” item that brings up a window with all your keywords.

From this window, you can select multiple photos, and then click the keyword buttons to assign/unassign keywords to the entire selection. You can also drag keywords up to the “Quick Group” area above and assign one letter keyboard shortcuts to them. For example, if I have “n” assigned to the keyword “nebula”, anytime I have something selected in the main iPhoto window, I can just press “n” to add/remove the “nebula” keyword from the selected photos.
I think this is the first version of iPhoto that really has a good interface for assigning keywords. Don’t know what took them so long, but there it is. My only gripe would be to have a button available somewhere in the bottom section of the window to bring up the keywords window, as I can see many people never even realizing that it’s available. I was actively looking for it, and it took me a good couple of minutes to find it.
There are many other large and small new features in iPhoto 7, which I may go into in more detail later, but those are the things that popped out at me in the first couple of hours of playing with it. I’ll be posting more later with other nuggets as I find them.
