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Apple iCloud: Broken by Design

iCloud (formerly has been broken for years in so many ways. But it’s currently so broken as to be unusable and I don’t know how to fix it.

Consider what happens if one turns on iCloud syncing for Safari bookmarks. The dialog presents itself. The answer is “no, I want to WIPE OUT what’s on iCloud with what is on this machine”. But that is not a choice.

The message is highly misleading: it uploads and downloads, merging both ways, which means a huge mess on the local computer. Continues below...

The Apple iCloud “Make a Huge Mess?” dialog

The merge process makes a huge mess:

If Cancel is chosen, then nothing happens. If Merge is chosen, then the following occur:

  • The local bookmarks are retained, but mangled and merged in with the detritus from iCloud.
  • A regurgitated hairball of every bookmark that I’ve ever created is carpet-bombed onto my local machine.
  • Apple’s default bookmarks (which I’ve deleted locally) are inserted for good measure.
  • Duplicates are created in many cases, and some bookmarks are damaged by changes to the URL that clearly belonged to other bookmarks.
  • There is no “replace iCloud with local Safari bookmarks” option.

It’s immensely frustrating. Is it really real? Who can dream up something this convoluted?

It’s not just my computer; I’ve spent hours helping a friend several times. As soon as syncing is enabled, the same mess happens, destroying the whole organizational structure.

So I figure: “let me go to and look for a Safari bookmarks thing, delete the hairball mess and then maybe it will work?” But there is no such management tool anywhere I can find anywhere in iCloud.

On another computer, I deleted all bookmarks, thinking maybe if I merged I’d get a snapshot of the hairball. I then did Merge several times with nothing showing up—zero bookmarks. So apparently one gets hairball or nothing.

Anywhere out there who knows how to manage the iCloud hairball—let me know.

Where can I un-hairball my Safari bookmarks?

Reader comments

Delete and pray

Many readers wrote to suggest that I follow a procedure consisting of essentially the following:

  1. Save off a copy of bookmarks via the Export Bookmarks command in Safari on a Mac.
  2. Delete all bookmarks on all Macs and phones (easier said than done on phones, best to “Replace All” in iTunes).
  3. Import bookmarks previously saved on one computer.
  4. Enable syncing on all computers.
  5. Pray like hell.

This sometimes works. For example, my laptop has no bookmarks now for the last 12 hours. Wonderful.

Furthermore, the same issues just pop up again: I delete or rearrange bookmarks on my main computer, and then all the deleted and rearranged stuff pops up from the other Macs and makes a huge mess. I can’t go through this pain for 4 Macs and three iPhones over and over.

Martin D writes:

iCloud is indeed broken by design. It is also opaque, disconcerting, and from time to time, disastrous. And sometimes it “just works” as advertised.

Your post suggests to me you expect it to work like iTools/.Mac/MobileMe/iSync syncing. It does not. iCloud has nothing whatsoever to do with those prior services. It's a completely different model.

iCloud appears to be a relatively “dumb” service in the sense it’s little more than a file syncing system; data sync is accomplished through it by way of a few conventions, client-side APIs and a lot of misery on the part the part of the hapless developer. The theoretical advantage to iCloud’s dumbness is a certain kind of robustness on the server side. The all-too-practical disadvantage of the approach is the absence of robustness on the client side.

One of the biggest problems with iCloud is its highly variable—and sometimes jaw-dropping—latency. I've seen it take as long as 25 minutes to propagate a change. Latency is particularly a problem when a client service is first brought on line. Sometimes it simply fails to get going on its own without a kick (reboots, etc.). Consequently, you can have everything enabled correctly on the client, but precisely zero data is flowing. I've found that deliberate patience is a crucial part of troubleshooting iCloud services. I've had to reboot multiple times and wait as long as 90 minutes (!) to jumpstart syncing with certain applications.

Stop flipping the sync services on and off. Turn on the ones you want and leave them on. Give the system time to stabilize. If you're left with a mess in your bookmarks, that's probably a tragically accurate representation of what's in your iCloud bucket. The key is that you're seeing the exact same mess on all the devices you want in sync. Once you're seeing that consistency—and ONLY once you’re seeing that consistency—choose one device and start cleaning up the mess. Periodically, check the other devices to verify that your cleanup actions are propagating. Remember that changes may sync immediately or may take many minutes to propagate.

MPG: I’ve been through this (with patience) many times. I’ve had everything perfect at my friend’s house on three of his Macs (he is not a savvy user so I help him), and then he calls me 3 days later to say it’s all screwed up again.

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