Why will photos not sync with VPN on????

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Level 1

8 points

Why will photos not sync with VPN on????

I have just updated to the latest version of macOS High Sierra Version 10.13.6 I have a VPN, ExpressVPN which is updated.

My photo's, messages and Lastpass apps have not been syncing since the new version of Sierra and Apple care denied it's their product. I have fixed the LastPass not working with Safari issues, setting in preferences of Safari about blocking all cookies etc, Apple care did not find it. Apple care fixed messages issues by us deleting all folders deep in the registry of the library in Applications.

ExpressVdoes do not have any known issues with the new version of 10.13.6. Apple care keeps blaming third party app and I keep telling them ExpressVPN has told me it is them, its Apple. They suggested that Apple is non-compliant when it comes to third-party apps. If I have VPN on the desktop and I take pictures on iPhone and it will sync to my icloud account online immediately and when I open the photos app on the desktop it just keeps stating updating. It can find the number of photos it needs to update but does not do it, it stays that way for hours I. If I turn off vpn and it will update almost straight away, I have done diagnostics with Apple engineers and they currently have not resolution, it has been 3 weeks now.

Posted on Jul 13, 2018 12:39 AM

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Answer 1

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Alfmac Author

Level 1

8 points

Jul 14, 2018 6:06 AM in response to léonie

Hi guys,

Okay, so I have spoken to ExpressVPN and now resolved the issue.

Whoever is currently has the same issues with ExpressVPN and current macOS High Siera version 10.13.6 (current in my part of the world as of today's post)

Okay, I have spoken to ExpressVPN and they have helped me fix the issue.

I had what is called an OpenVPN connection issue and this was fixed with the following issue steps:

Send off diagnostic to VPN provider first, to run diagnostic.

https://www.expressvpn.com/support/troubleshooting/log-items/unable-to-connect-c ant-assign-requested-address-code49/

The above step is a Flush routing table, it only takes 3 minutes and I am not tech savvy. If at this stage it does not work do not forget to shut down and restart Mac/PC then it should be fine.

After doing the steps in the link, please check if the syncing issue if the resolved. If it persists, please try these steps:

Start the ExpressVPN application.

Click the " [☰]" button (located on the upper-left of the app).

Click on Preferences/options...

Click on the Protocol tab on the top.

Select "L2TP"

Click "OK" then connect the VPN again.

This step worked for me and now all is good for me.

Thanks to all who responded to my question.

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Answer 2

léonie

Level 10

200,645 points

Jul 14, 2018 5:21 AM in response to Alfmac

It can find the number of photos it needs to update but does not do it, it stays that way for hours I. If I turn off vpn and it will update almost straight away,

Apple added new security measures in High Sierra. Some older security software is not compatible any longer. Several users are now having issues with iCloud syncing, if they are using a third-party VPN.

You will have to keep your VPN turned off to be able to sync with iCloud, until your VPN software has been updated by the vendor to work with Apple's new security measures.

it will not help to put the blame on Apple, even if apple changed the rules. If you are using third-party software on your Mac it has to be compatible with your current system or it will be causing problems.

Resolve issues between iTunes and third-party security software - Apple Support

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Answer 3

Jul 14, 2018 5:22 AM in response to Alfmac

As léonie said it seems that you're not the only one having issues with iCloud through VPN. Some users fixed the issue installing an App Store version of the client and choosing P2P enabled servers.

It seems to me that ExpressVPN doesn't offer a specific App Store client and probably using a OpenVPN compatible client like Tunnelblick would not solve the problem either.

Does ExpressVPN app have a filter feature? Some VPN apps let you choose what app is tunneled/or excluded.

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Answer 4

Alfmac Author

Level 1

8 points

Jul 13, 2018 6:08 AM in response to léonie

Hi Leonie

Thanks for the information, I have created a work ticket with my VPN to see if your information is valid. I will repost when I get a response.

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Answer 5

léonie

Level 10

200,645 points

Jul 13, 2018 6:35 AM in response to Alfmac

Yes please, post any news you can receive - there are several users having problems with the syncing of iCloud Photo Library and VPN enabled after tupgrading to High Sierra.

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Why will photos not sync with VPN on????

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