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iCloud problems when connected to VPN

Hi there,

I'm having trouble using iCloud's Documents & Data sync when connected to a VPN through Viscosity. I'm running OS X Mavericks 10.9.2, Viscosity for mac version 1.4.7, and am using Private Internet Access. As soon as I connect to the VPN, I instantly lose all document syncing through iCloud, and syncing is immediately restored to normal upon disconnect. Other iCloud services, such as Calendar and Notes syncing, seem to be unaffected.

Anybody else having the same issue, and is there any solution to this?

Cheers
Hi major77,

Do you have Back to My Mac enabled for your iCloud account? If so, does disabling it resolve the issue? You can check this by going to the Apple Menu->System Preferences->iCloud.

Cheers,
James
When I first narrowed the problem down to Viscosity, I did have Back to My Mac enabled, but I've since disabled it and re-started my computer based on advice in some other threads I came across. Unfortunately though it hasn't made any difference.
I've got a few more details to add to this, if it helps:

    - I am also running Viscosity on an old MacBook running OS X Lion 10.7. iCloud documents and data sync continues to work just fine on that machine while connected to PIA through Viscosity. The Viscosity settings are identical on the two computers as far as I can tell.
    - On the computer I'm having trouble with (a 2011 Mac Mini), I've reverted to using Tunnelblick to connect to the VPN as it doesn't cause me the same problems with iCloud syncing that Viscosity is causing.
Anyone?

I've been trying to look into the problem a little more, and went so far as to do a clean install of Mavericks on a separate partition to see if something in my setup is causing the problem. Even with a clean install, and nothing else installed other than Pages (to test doc syncing) and Viscosity, as soon as I connect to PIA through Viscosity my iCloud documents refuse to sync.

This tells me that I can't possibly be the only one experiencing this issue. Is it possible that something in the OpenVPN configuration files downloaded from PIA could be causing the problem? If not, I can't see the cause being anything other than some problem with Viscosity itself.
Hi major77,

I can confirm we see the same behaviour in testing. It appears iCloud's Document syncing feature is linked to Back to My Mac's underlying process, which Viscosity disabled while connected. We spent a solid two days trying to see if we can work around needing to still disable this under Mac OS 10.9, with no luck.

Instead we've added an "Disable Back to My Mac while connected (recommended)" option under Preferences->Advanced to the latest beta version. Turning off this option should allow Documents & Data to sync while connected again. However BTMM is known to cause both DNS and IP assignment issues, so if you find your connection is not working correctly (even if you have turned off BTMM in the iCloud settings area) you may need to consider turning it back on.

The latest beta version can be downloaded from:
viewtopic.php?p=134#p134

Cheers,
James
Hi James,

Thanks for the reply, and for taking all the time to look into this! I gave the beta a try – still no go for me though, even with that checkbox disabled (BTMM is off too).
Where has this setting gone to? My Photos won't sync whilst connected to my VPN.
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