Sadly, every single time. Why? Well, it's about security. Apple is doing its best to protect its customers. There was a feature in earlier iOS versions to block USB and that option is now removed in favor of having it require the passcode every time. To enable a USB connection you have to authenticate every time.
Have you ever been traveling internationally and seen those public phone charging stations? Some of them are not just DC power they have hacker devices that make a USB connection, deploy an exploit that hacks an iPhone and grabs all your data. You plug into what you think is a free charging station and it pops up asking for your passcode, you know something is NOT RIGHT.
Various governments, intelligence agencies, and police have hardware devices (one of which is called a GrayKey) that use exploits to crack into an iPhone over the Lightning port. It's a real threat for those who live or travel through countries with repressive regimes. Did you notice the new Lockdown mode? That is intended for people who are under aggressive cyber attacks. Such as journalists, politicians, etc. being targeted by nationstate cyber warfare units. It's not all about the nationstate bad actors, cyber criminals use many of the same attacks.