Should I lock customers in or earn their loyalty?

The tension you feel is real, and it is worth listening to. Lock-in makes the next quarter easier. Loyalty makes the next ten years possible. You are being pulled between a quick grip and a lasting bond. Ask yourself a simple test: if leaving were easy, would they still stay? If the honest answer is no, then what you have is not loyalty, it is a cage, and people resent a cage even when they cannot leave it. Trust built on freedom is stronger than any contract that traps. Pick one place where you make leaving hard, exporting data, canceling, moving on, and make it easy. Watch what happens. A customer who stays because they want to is worth more than three who stay because they are stuck.