[D43m0n]

I think I have the same issue.

Laptop and software:
I'm using a 2021 14 inch MacBook Pro with M1 Pro cpu running macOS Monterey 12.6.2. I have DisplayLink Manager 1.8.0 installed.

Here's how it's connected:
I use 2 external monitors. One is a Philips 243B1JH and the other is a Philips 241B7Q. The 243 has a USB-C connector. I use this connector on my MBP. The 241 Philips monitor has the USB3 (type A) connector plugged in the 243 monitor, so they're daisy chained.

Here's what I experience:
When I plug in the USB-C cable, it all works just fine. I can extend the display to both Philips monitors and it all works as expected. Now when I leave my desk, I always lock the screen as a habit. All displays go black indicating the monitors go into power save mode. This is also as expected.
Now when I come back at my desk and hit any key on the keyboard or move the mouse, the screens wake up. The 241 monitor is always slow but when I log in, the display on the 241 monitor is either a frozen image of just my background and nothing more. The MBP doesn't see it is connected anymore. Or, in some cases, the 241 is mirroring the display of the internal (builtin) MBP monitor in a low resolution. It's either one of those situations.

What I do to get it working again:
In order to get the 241 to work as expected, I can do two things;
1) either power off and power on the 241 monitor using the power button on the right bottom located on the front of the 241 monitor. This lets the MBP see the 241display again and it works as expected with both external monitors.
2) Stop and relaunch the DisplayLink Manager software. This also makes the MBP see the 241 display again and it works as expected with both external monitors.

Bad user experience:
This is very annoying behavior because my windows I have open are constantly being rearranged when I need to perform either a power off/-up of the 241 monitor or relaunch the DisplayLink Manager software. The windows get cluttered on one active display, either the builtin MBP display or the 243 monitor that is connected via USB-C.

Other things I've tried:
I have also tried to connect the 241 monitor via a USB-A to USB-C adapter directly to another USB-C port on the same MBP, essentially each monitor has it's own direct connection to a USB-C port on the MBP without daisy chaining the monitors, but this makes no difference.