To provide a folding and inserting method and a folding and inserting machine capable of stably folding a packaging bag, which is filled with contents, along a predetermined folding position in a uniform state, and inserting it into an outer container while maintaining this folded state.

The folding and inserting machine has a first holding means 21 which is provided to an intermittently rotating table 15 of a folding means 13 and whose left and right holding members 22 and 31 hold and hang an upper part of a bag W having first and second filling portions W1 and W2, both being filled with contents. When the bag is moved to and stopped at a second step, a folding plate 119 of a folding unit 95 rotates in the state of placing the second filling portion thereon and rotates the second filling portion around a sealing part C to superpose it on the first filling portion. A lower part of the second filling portion, which is held up, is held by inside and outside holding members 57 and 58 of a second holding means 56. When the bag is moved to a third step in this state, it is taken out by a handling robot 153 in a take-out and insertion means 151 and is inserted into an outer bag L held by grippers 174 in a packaging means 171.