A patch pump assisting system comprising: a disposable device; and an assisting device including a soft cannula insertion mechanism configured to at least insert a soft cannula in tissue, wherein the disposable device includes: a housing; an first exit port septum configured within a cup opening; an exit port well; and an second exit port septum; and a soft cannula having a lumen, and a rigid cannula having a lumen, and wherein: the soft cannula and rigid cannula each include at least one lateral opening (378, 337) along a length thereof and a tip; the housing is configured for placement on the skin of a user for cannula insertion and remains after insertion; prior to insertion, the rigid cannula is positioned within the soft cannula with a portion of both cannulas (366, 377) initially traversing the first exit port septum and the tip of the rigid cannula is positioned within the exit port well; after insertion, the lateral openings of the soft cannula are positioned within the well and the tip of the soft cannula is positioned within the body. a disposable device; and an assisting device including a soft cannula insertion mechanism configured to at least insert a soft cannula in tissue, wherein the disposable device includes: a housing; an first exit port septum configured within a cup opening; an exit port well; and an second exit port septum; and a soft cannula having a lumen, and a rigid cannula having a lumen, and wherein: the soft cannula and rigid cannula each include at least one lateral opening (378, 337) along a length thereof and a tip; the housing is configured for placement on the skin of a user for cannula insertion and remains after insertion; prior to insertion, the rigid cannula is positioned within the soft cannula with a portion of both cannulas (366, 377) initially traversing the first exit port septum and the tip of the rigid cannula is positioned within the exit port well; after insertion, the lateral openings of the soft cannula are positioned within the well and the tip of the soft cannula is positioned within the body. a housing; an first exit port septum configured within a cup opening; an exit port well; and an second exit port septum; and a soft cannula having a lumen, and a rigid cannula having a lumen, and wherein: the soft cannula and rigid cannula each include at least one lateral opening (378, 337) along a length thereof and a tip; the housing is configured for placement on the skin of a user for cannula insertion and remains after insertion; prior to insertion, the rigid cannula is positioned within the soft cannula with a portion of both cannulas (366, 377) initially traversing the first exit port septum and the tip of the rigid cannula is positioned within the exit port well; after insertion, the lateral openings of the soft cannula are positioned within the well and the tip of the soft cannula is positioned within the body. the soft cannula and rigid cannula each include at least one lateral opening (378, 337) along a length thereof and a tip; the housing is configured for placement on the skin of a user for cannula insertion and remains after insertion; prior to insertion, the rigid cannula is positioned within the soft cannula with a portion of both cannulas (366, 377) initially traversing the first exit port septum and the tip of the rigid cannula is positioned within the exit port well; after insertion, the lateral openings of the soft cannula are positioned within the well and the tip of the soft cannula is positioned within the body.