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sync

Fun with iTunes’ new math

Unlike my previous incidents with iTunes and iOS devices, today’s report isn’t on a sync problem per se.

It’s more like a math problem which then leads to a sync problem. Here’s the tl;dr version: I have an iPad with 5GB of free space, and I cannot add a 1.8GB movie to it, as iTunes eventually tells me it needs another 526MB of space in order to do so.

During the attempted sync of this movie, iTunes displays some horridly bad math skills; just watch the video to see.


Here’s the video at its full size (1164×1056).

I have no idea how to resolve this, short of restoring the iPad, which I’d rather not do. (I’ve already unsynced and resynced everything, in an attempt to straighten out the math, but to no avail.)

Revisiting iTunes/iOS sync issues

After getting my iPhone 6 in early October, I was initially excited by all the cool tech in my new phone. Until I tried to sync it, that is. I eventually got so frustrated that I emailed Tim Cook for help. From that email, I wound up talking to Apple’s engineers, who eventually solved my sync issues—it turns out they were related to duplicates of long-ago-purchased songs.

Welcome to
Sync Hell

And for a while, things were great in iPhone 6 land. Then I ripped a few new CDs, and noticed that they didn’t show up on the phone. Uh oh. Even worse, when I looked at my iPhone in iTunes, the Music section contained hundreds, if not thousands, of the dreaded gray dotted circles.

This seemingly innocent symbol means that the indicated song did not sync—the information about the song made the journey to the phone, but the song itself did not. Argh! Read on to see how I muddled through this issue, with some advice that may, or may not, help you with your own sync issues.

If you don’t want to read everything, here’s a tl;dr version:

  • My iPhone sync issues returned, along with a huge-fake-but-limiting amount of data shown in Other.
  • There’s a known-to-Apple “very slow performance” issue in iOS/iTunes that can make some iPhones sync very slowly (fixes have been made, but not yet released).
  • A factory restore failed to complete until I rebooted the iMac.
  • After the restore, the sync worked, but I still had a huge Other category.
  • After the iOS 8.1.1 update, the huge Other category vanished.
  • I had to manually unsync/resync a number of songs to clear their gray dotted circles.
  • It may help to do a voodoo dance, sacrifice three Nokia phones, and rub your stomach while patting your head before syncing.

Read on for the gory details…except maybe for that last item, which I totally made up.

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A nasty little iTunes/iOS bug may be causing media sync issues

November 18th update: My sync issues returned, but due to a different cause this time. Details in this post.

After complaining to Tim Cook, and separately starting a (now closed) support ticket, it appears that my iOS/iTunes sync nightmare has finally come to an end!

I have not seen a progress bar that busy since the day I brought my iPhone 6 back home. Whatever I tried, iTunes simply would not sync everything in my library. In the end, the problem turned out to be as simple—but as deadly—as this:

In the current version of iTunes/iOS, there’s a bug that only appears when you have duplicates of purchased songs. When encountered, a duplicate of a purchased song will (almost always) cause iTunes to silently stop syncing.

This is a known-to-Apple issue, and it will be fixed in a forthcoming update. I’m fairly certain it’s an iTunes bug, but as Apple didn’t clearly state which it was, I’m calling it iTunes/iOS. Either way, until it’s fixed, it’s a really bad bug.

Here’s what happens: If you have duplicates of purchased songs, iTunes simply silently stops syncing when it hits one of those duplicates. From your perspective, it will look like everything is working—iTunes never throws an error, and it proceeds through all six (or seven or whatever) steps of the sync process, as seen in the status window of iTunes.

But behind the scenes, nothing is happening—at least, nothing relative to syncing your files. As seen by my troubles, this can be incredibly frustrating and hard to fix.

Continue reading to see how I was able to finally (with Apple’s help) get my devices syncing again—the tricky part is finding all the duplicates, because they’re not all obvious. Also note that if you are not having sync issues, I wouldn’t worry about duplicates—no need to endanger what’s already working well!

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An iPhone 6, (no) movies, and me

On Friday, I received my new iPhone 6, which I really like—a lot, in fact. Over the weekend, however, I discovered that my new iPhone does not like iTunes—at least not syncing my movies via iTunes.

Things started great, with the arrival of the new iPhone 6 on Friday afternoon:

From there, though, things didn’t go exactly according to plan…and I documented my progress (or lack thereof) via Twitter over the weekend. Read on for the full story, as told in 140 character increments.

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I asked Tim Cook for tech support…and you should, too!

Those following me on Twitter this weekend will have noticed that my (lovely, stunning, amazing, I am keeping it) iPhone 6 is not playing nicely with iTunes. I’ve invested over 10 hours—in one day—just trying to get music and movies onto my iPhone.

Frustrated as hell, I decided ask Tim Cook for some tech help, not that I have much hope of any sort of reply. Emails to his address, however, are apparently all read by someone. For those having similar issues, I think it may be useful to also send your feedback in Tim’s direction; his email address (not a secret, published in many places) is tcook at Apple’s domain. Perhaps if there are enough voices providing feedback in high places (not that Tim reads these himself), we might see some action.

Further update: I have now done two full system restores. I did the second just before bed last night, and let the iPhone sync overnight. On wake, everything worked! So then I added in a few more movies, and—of course—they failed to sync. So now I’m back where I started, oh so many hours ago.

Anyway, For the curious, here’s the tech support request I sent to Tim yesterday.

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iCloudy with a 100% chance of stupidity

I use a lot of cloud services for file storage, primarily Dropbox, but also Box and (begrudgingly, for certain shared projects) Google Drive.

I also use iCloud, but not in any way that would be considered a true cloud file storage service. I use it strictly as a sync service for contacts, calendars, reminders, notes, Safari; I also use Back to My Mac.

But that’s it; I don’t use iCloud for cloud-based file management at all. Why not? Because iCloud in its current implementation is chock full of the stupid, at least for those of us who still use and rely on OS X.

Stupid #1: Not enough free space, and too costly for more

A quick comparison chart shows just how far out of line iCloud is with other cloud-based services:

Provider Free Tier 1 Tier 2 Tier 3
GB GB $/Yr $/GB/yr GB $/Yr $/GB/yr GB $/Yr $/GB/yr
Box 10 100 $60 $0.600 1000 $180 $0.180
Dropbox 2 100 $100 $1.000 200 $199 $0.995 500 $499 $0.998
Google Drive 15 100 $24 $0.240 1,000 $120 $0.120 10,000 $1,200 $0.120
iCloud 5 15 $20 $1.333 25 $40 $1.600 55 $100 $1.818
Pricing sources: Box • Dropbox • Google DriveiCloud
Note that you can get additional free space on Dropbox through referrals and uploading images; Box occasionally offers a promo with 50GB of free space.

Kirk McElhearn covers this price and space issue in more detail in his blog post, Why Does Apple Only Offer 5 GB Storage with iCloud?.

I agree with him; if iCloud wants to attract more users, it needs more free space, and more competitively priced upgrade plans.

Read on for more of the stupid…

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