Most people arrange travel cover in the last few days before a trip. A fair number buy at the airport. Late purchase forfeits one of the two things cover provides. Cover operates across two distinct windows. The trip itself is the obvious one. The weeks before you leave are also covered. Once the trip starts, cancellation cover has nothing left to do. Late arrangement compresses months of protection into a day. Disruption arrives more often in the run-up than during. The ordinary interruptions of life that arrive without warning. Whether it is recoverable depends entirely on when you bought. The price is generally the same whenever you arrange it. The delay costs protection and saves nothing. Arranging at the point of booking is the sensible default. An annual arrangement removes the timing question entirely. The break-even is usually around two or traveltweaks article three trips. An annual policy also covers spontaneous trips. A gap between renewals catches people out. Most providers will not cover a journey already underway. The remaining days can still be protected. The travellers who never lose money on cancelled trips generally sorted it when they booked.