The indiscriminate enthusiasm surrounding smart contracts detracts from the simple fact that neither blockchains nor smart contracts interface with the outside world. A smart contract devoid of access to information about real world events is, however, of limited commercial significance. To gain relevance in InsureTech, smart contracts must be able to release funds in response to events extrinsic to the blockchain, in the real-world. For that to happen, they must be provided with information about such events (“off-chain information”). Examples are weather data, flight statistics, market data, exchange rates or the occurrence of natural disasters. Entities providing such information are called “oracles.” In principle, smart contracts exist on-chain and “codify the conditions” of release of the asset controlled/held by them. Oracles exist off-chain and provide information regarding the fulfilment of such conditions. After providing the legal and commercial background, this chapter will focus on the fact that (a) consensus algorithms cannot determine or validate the correctness of any off-chain information and (b) oracles obtain the off-chain information from external information sources and, in principle, are also incapable of establishing its correctness. It will emphasize that as oracles do not share any of the attributes of blockchains, they are neither trustless nor secure. There is no technical mechanism preventing them from providing incorrect information. This is known as “the oracle problem.” The off-chain information may be incorrect for many reasons, both technical and non-technical. Technical reasons may derive from programming errors or external interference. They may concern the data source(s), the oracle itself or, in the case of oracle networks—the individual nodes, as well as the rely mechanisms between the data sources and the oracles. Non-technical reasons concern the fact that individual oracles, nodes in an oracle network as well as data sources may be corrupted. The chapter will discuss efforts to solve the oracle problem and demonstrate that certainty cannot be achieved by purely technical means. It will also address an important collateral issue: the fact that oracles are generally unable to deal with non-binary query types. Consequently, the conditions of releasing funds must be simple, and their fulfillment must be capable of objective, binary verification. The complexity of the world and the payout conditions must be adapted to the limitations of the oracle and the available data sources. But: what would happen if the temperature in Venezuela did in fact drop but the farmer’s crops were not destroyed, or only partially destroyed? Taking technology as a point of departure, the chapter re-examines popular claims concerning the potential of smart contracts to improve consumer insurance.