VPN Breaks iCloud Synching

Why can't my devices synch when I use a VPN? Other apps that synch (e.g. Firefox bookmarks) don't seem to have a problem when I use my VPN. Example: if I add a bookmark in Safari on my Mac with a VPN active, it doesn't show up on my iPad until I turn off the VPN on both devices for several hours at least.

MacBook Pro 16″, macOS 15.3

Posted on Feb 6, 2025 10:52 AM

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6 replies

Feb 7, 2025 7:54 AM in response to ichosethered1

ichosethered1 wrote:

Why can't my devices synch when I use a VPN? Other apps that synch (e.g. Firefox bookmarks) don't seem to have a problem when I use my VPN. Example: if I add a bookmark in Safari on my Mac with a VPN active, it doesn't show up on my iPad until I turn off the VPN on both devices for several hours at least.


Yes VPN have been known to cause issues...


you can file a bug report / submit your Apple Feedback here: Product Feedback - Apple




If your work mandates the use of a point to point VPN— contact your work IT network admin, and verify if they block or not access to the Internet which is common practice on a work network.


otherwise might be time to re-think the usage.


see: Public VPN's are anything but private or safe

https://krebsonsecurity.com/2024/05/why-your-vpn-may-not-be-as-secure-as-it-claims/

https://gist.github.com/joepie91/5a9909939e6ce7d09e29

https://www.eccu.edu/blog/cybersecurity/5-reasons-why-you-should-not-use-free-vpns/

https://krebsonsecurity.com/2024/05/is-your-computer-part-of-the-largest-botnet-ever/

https://www.pcmag.com/news/the-feds-have-some-advice-for-highly-targeted-individuals-dont-use-a-vpn

Feb 7, 2025 8:24 AM in response to ichosethered1

VPN:

A virtual private network, or VPN, is a private connection over the Internet from a device to a specific network.  VPN technology is widely used in corporate environments. If you need to be "present" on an institutional network, a VPN is a great tool for accomplishing this. it is generally issued and controlled by the institution.


Almost all other uses are a SCAM. There is generally no need for you to have a private connection to a VPN vendor's Network, except to make it easier for them to harvest your data to sell. There is NO security advantage whatsoever in using a VPN. Your connections are already encrypted in most cases.


Why are there so many VPN vendors?

Because they cannot resist the 'easy money' for doing next-to-nothing.


If VPN vendors just stopped there, it would be bad. But many of these packages also insist on scanning all your files, non-stop, -- nominally looking for viruses, but who knows for sure what data they are harvesting. Their non-stop file reading punishes your computer's performance in the process.


Some also break into your other secure connections so they can be FIRST to examine your data, often leaving your Mac MORE vulnerable to attack.


https://gist.github.com/joepie91/5a9909939e6ce7d09e29


Feb 16, 2025 10:43 AM in response to leroydouglas

I use ProtonVPN. It’s part of my Proton Unlimited (VPN, email, cloud storage, wallet, etc.) paid subscription from a Swiss based security company whose apps are open source and audited. I would never use a ‘free’ VPN—nothing is truly free! I use this VPN when connecting to hotel WiFi and other unsecured networks. Would you connect to the airport WiFi without a VPN? 


Thank you for your reply. We could discuss the security of VPNs and the lack of government regulations on companies invading our privacy for hours, but that was not the topic of my post. 


I’m aware of Apple’s product feedback site, but this question does not fit any of their categories and so, would probably go nowhere. 

Feb 16, 2025 11:02 AM in response to ichosethered1

ichosethered1 wrote:

I use ProtonVPN. It’s part of my Proton Unlimited (VPN, email, cloud storage, wallet, etc.) paid subscription from a Swiss based security company whose apps are open source and audited. I would never use a ‘free’ VPN—nothing is truly free! I use this VPN when connecting to hotel WiFi and other unsecured networks. Would you connect to the airport WiFi without a VPN? 

Yes, I do it all the time but I am careful what I am doing and I use secure protocols. A non point-to-point commercial VPN does not provide any security. Why would you route all your data through a third party VPN provider who does whatever they wish with your data then routes your data to its destination just as you would have? These commercial VPN providers do not have special secure routes or connections to Internet destinations.



Thank you for your reply. We could discuss the security of VPNs and the lack of government regulations on companies invading our privacy for hours, but that was not the topic of my post. 

I’m aware of Apple’s product feedback site, but this question does not fit any of their categories and so, would probably go nowhere. 


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VPN Breaks iCloud Synching

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