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I've been trying to ditch Google Chrome and start using Safari both on my MacBook (OS X Lion) and my Windows 7 desktop.

After setting up iCloud on my Mac, I've set up bookmarks sync with Safari via iCloud on the Windows machine, as suggested in this question. The initial sync went well, and all of my bookmarks appeared in Windows Safari.

But as far as I can see, the new bookmarks are not synced. Neither do new bookmarks added on Mac appear on Windows, nor the happens the opposite.

I've tried to sign out of iCloud on Windows, then sign back in; tried unchecking the bookmarks sync option and turning it back on. It didn't help.

Windows Safari is ver. 5.1.7, OS X Safari is ver. 5.1.5.

I wasn't able to find a way to see the bookmarks in iCloud online, so I have no idea about which side of the sync is faulty.

I haven't found any suggestions online, apart from the advice to wipe all bookmarks and start over, which seems a sad case of cargo cult to me.

How can i troubleshoot the issue? Is there any sync status reports or logs, or a way to see the bookmarks stored online? Or should I do cargo cult, after all?

By the way, i don't have any iOS devices or other Macs to test against.

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I diagnosed and fixed my sync problem. It's been three or four days of bookmarks syncing without any hiccups.

Narrowing the scope

The original problem was so tough because I had no simple way to find it whether the Mac Safari, or Windows Safari, or both, failed to sync.

To find out if the iCloud on Windows works, do this:

  1. Change the Sync bookmarks with option in iCloud to Internet Explorer, wait a bit (sadly, iCloud doesn't seem to display any kind of sync progress anywhere).
  2. Open Internet Explorer, add a bookmark or two, wait to give iCloud a chance to sync.
  3. Change the Sync bookmarks with option in iCloud to Safari, again, wait.
  4. Open Safari, check if the bookmarks added in Internet Explorer are there.
  5. Add another couple of bookmarks in Safari, wait.
  6. Change the Sync bookmarks with option in iCloud back to Internet Explorer, wait.
  7. Open Internet Explorer, check if the bookmarks added in Safari are there.

Now, in my case, all worked OK on the Windows iCloud part, so next thing I had to do was diagnosing the Mac part.

Fixing the problem

Apple KB article iCloud: Troubleshooting iCloud Bookmarks was an excellent source of help, once I knew which part of the setup to fix.

The steps that actually helped me in my Mac Safari problem case were these (see Troubleshooting iCloud Bookmarks update/setup issues on OS X Lion):

  1. Quit Safari.
  2. Choose System Preferences from the Apple () menu and then choose iCloud.
  3. Remove the checkmark in the checkbox next to Bookmarks.
  4. Close System Preferences and wait about a minute.
  5. Open System Preferences and choose iCloud
  6. Replace the checkmark next to Bookmarks.
  7. Close System Preferences.
  8. Open Safari and test to see if the issue has been resolved.

For Windows iCloud problems, there's a separate section, Troubleshooting iCloud Bookmarks update/setup issues on Microsoft Windows, which probably should be helpful as well.

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