There are three connections you are likely to meet. HDMI is the flat six-sided one, present on nearly every monitor and most laptops. DisplayPort looks similar but has one squared corner and a small latch, and it is the better choice on a desktop because it handles high refresh rates comfortably. USB-C is the small oval one, and it carries video only when the port supports it, which is usually marked with a small display symbol or a lightning bolt beside it. A USB-C port with no marking may be data only, and no cable will make it output video.
On a desktop with a separate graphics card, use the ports on the card itself, low down at the back of the case, not the ones on the motherboard higher up. When a graphics card is fitted, the motherboard outputs are frequently disabled, and plugging into them gives you a screen that never wakes up. This trips up more people than any setting in Windows.
Laptops have a limit on how many external displays they can drive, and it depends on the graphics hardware rather than on the number of ports. Most modern business laptops handle two external screens without difficulty, and a docking station makes that a single cable at the desk. If you are choosing hardware for a new setup, the ports on the machine matter more than the specification sheet, which is something we cover on our new computer setup page.
Adapters are where quality shows
A cheap USB-C to HDMI adapter is a common cause of a screen that flickers, drops out, or refuses higher resolutions. If everything is configured correctly and the picture is still unstable, swap the adapter or the cable before changing any settings.