This was something that was more prominent during the Micro-USB era. The little metal "tabs" on the male end of microUSB connectors would start to wear out after a thousand+ plug/unplugs resulting in a loose connection that wasn't reliable.
With USB-C, the connector was designed consideration of a bunch of factors, one of which I would assume is lifespan of the end connectors - USB-c has thicker, more resilient plastic hooks built into the inside of the male plug and stronger mating latches in the female end of the connector.
It when You need to adjust cable multiple times until connection happen, and then work very careful to not move anything.
Ports sometimes are very fragile. My old laptop has only 2 of 4 USB ports working.
Connectors are rated for a given number of connect/disconnect cycles. For USB-A it's a minimum of 1500[1].
If your laptop has a cheap connector which isn't rated for more, and you do two cycles a day (start/end of day, start/end lunch), then you'll go through the rated number of cycles in less than two years.
Doesn't mean the connector will fail right away but it might start to act up. Connectors are not forever.
