Everytime you book additional insurances that cover small amounts of money. Like a airplane ticket insurance (that only covers the fee of the ticket if you cancel). Or a additional rental car insurance.
Assuming that Insurance companies are not stupid and only offer an Insurance that is +ev for them, that means its -ev for you. If you are in the financial situation that 1-5k$ wont ruin you its rational to NOT take these kind of insurances.
Every spot in life that you encounter that can be seen purely from an EV perspektive should be played as that. Only exceptions are longtail ruinous outcomes, like House Fire insurance, Health Insurance. Thats why in many western nations these types of insurances are mandatory.