An object insertion system includes an insertion portion, a first information generator, a storage unit, a second information calculator and an output unit. The first information generator includes at least one sensor and is configured to generate first information indicating at least one of an insertion state and an operation state of the insertion portion in a body cavity. The second information calculator is configured to calculate second information based on the first information generated by the first information generator and at least one of third information and fourth information stored by the storage unit, the second information being operation support information to insert the insertion portion to perform a predetermined work. The output unit is configured to output the second information.