Cover typically gets bought during the packing stage. Some arrange it after checking in. Late purchase forfeits one of the two things cover provides. Cover operates across two distinct windows. The journey is what people picture. Cancellation protection applies to the gap before travel. Departure ends that part of the policy. Buying the day before leaves it perhaps a few hours long. Most things that disrupt trips happen before they start. The ordinary interruptions of life that arrive without warning. Whether it is recoverable depends entirely on when you bought. There is no premium for buying early. You pay the same for less. Book the trip, traveltweaks guide arrange the cover, move on. People taking several trips a year often do better with continuous cover. The break-even is usually around two or three trips. An annual policy also covers spontaneous trips. Renewal dates deserve a note somewhere. Some offer restricted options at higher cost. Where a trip is already booked and uncovered, arranging now is still better than not. Anyone who has recovered a deposit after a cancellation generally sorted it when they booked.