Why has automatic update of Apps never worked normally on my iPhone?

Here’s more information on Private Relay→About iCloud Private Relay - Apple Support

Apple’s discussion of VPN→Check VPN (Virtual Private Network) and third-party software to help resolve network connectivity issues - Apple Support

And a general analysis of VPN use:

Something to think about→Don't use VPN - GITHUB

There are two legitimate purposes for using VPN:

• To allow access to a private network such as a school or business when you are not on site. 
• To allow access outside of a country with a repressive government that has restricted Internet access. (This has suddenly become more important)

Any other use is risky, and can lead to problems like the one discussed in this thread. VPN disguises your location by making you appear to be somewhere else in the world. But you usually can’t control that “somewhere else”, and if it is in a location that an app isn’t approved for the app won’t work. Plus the fact that the provider of the VPN knows everything about you and your location, as well as what sites you access through the VPN. So you are totally dependent on the VPN provider’s honesty. As a start, if the VPN is free, DON’T USE IT. The provider has to make money somehow, and if you aren’t paying them then they are selling your private data to make money. But even those that charge can’t necessarily be trusted. For example, a few years ago Avast was caught selling user browsing data. They claim they have stopped doing so. 

You don’t really need VPN when using public Wi-Fi, because all communications between your device and the servers it accesses are end-to-end encrypted.

If you want VPN for privacy about the sites you visit, that’s not a good choice as discussed; instead you should download and use the TOR browser.

Automatic updates should occur overnight if the following is true

• you are on a good Wi-Fi, (from 15.4 iPhone 7 up, you may be offered cellular update)

• Plenty of spare storage – 6GB at least.

• on charge with more than 20%, OR

• off charge with more than 50%

• low power mode turned off.

• Fully working cellular network connection via your SIM.

• Check Settings, General to make sure you have no Beta profile installed.

• no VPN installed (Check Settings, General, VPN & Device Management)

Uninstallation of all 3rd party VPNs is a required condition, whether “reasonable” or not, except for VPNs to access a private business or school network (which is the intended purpose of VPN). VPN profiles seriously corrupt up the protocol stack just by being installed. And Safari does NOT come with pre-installed VPN. Apple does not call iCloud+ Private Relay a VPN, because it isn’t, and doesn’t work like a VPN. It disguises the IP address during browsing and uses an encrypted DNS connection.

Are asking about app updates and not iOS updates, which LD150 addressed, have you enabled app updates over cellular? Alternatively, if you want to update only over Wi-Fi you must leave the phone connected to power overnight (you should anyway, as it’s better for extending the useful life of the battery).

Go to Settings/App Store and turn on:

• Cellular Data (optional-see above)
• Automatic Downloads/App Downloads
• Automatic Downloads/App Updates
• Cellular Data/Automatic Downloads (optional)
• Cellular Data App Downloads —> Always Allow (optional)

JustinMichaelJoseph wrote:

Safari now comes pre-installed with the possibility of hiding our IP address with VPN? I am not using VPN when I am trying to run automatic updating of Apps. So do I have to uninstall Safari to get automatic updating of Apps to work? Also, millions of people live in autocratic countries and must use VPNs in order to get access to Facebook and Twitter.

As you apparently didn’t read or didn’t understand my response:

PRIVATE RELAY IS NOT VPN

PRIVATE RELAY IS NOT VPN

PRIVATE RELAY IS NOT VPN

PRIVATE RELAY IS NOT VPN

PRIVATE RELAY IS NOT VPN

Now go back and read my ENTIRE post.

If you are USB connected to the Mac fir a long time rather than on Wi-Fi, I may be wrong, but you will not get auto updates of apps or iOS OTA but the Finder (iTunes on Mojave and older) should show you that an iOS update is available ,

I only connect to Mac for syncing purposes for 20 minutes once a week so don't know how an iphone tethered long term will behave

For example, Safari on my Macs and iOS devices come with a pre-installed VPN feature.

Really? Apple does not think so.