I never use these companies chat features.

Historically, these chat interfaces were tied out to a call center somewhere on the opposite side of the planet. Now they're entirely prompt-engineered. So you used to be able to work a claim through chat without sitting on a phone call for hours at a time. But now they obscure their customer support phone number behind six layers of tabs and links, while shoving the "WOULD YOU LIKE TO CHAT WITH A REPRESENTATIVE" button in your face the whole way, fully knowing it doesn't actually connect to anything that will help.

But my biggest pet peeve is a lot of times I have ro get a supervisor to solve a problem that would take the customer service agent ten seconds to solve.

A lot of the agents are just working off of written prompts anyway. But they do get experience with these problems over time (or recognize a slew of the same problem coming in at once) and can cut through the shit to give you a real, human response. Sometimes that response is simply "We can't help, because of widespread technical / systems issues", but that's better than being bounced through an automated service that feeds out generic non-answers and useless how-to guides.