Downhole tool retrieval and setting system

A method of retrieving a whipstock used to form a window in a wellbore, wherein the window is located adjacent to the whipstock, comprising:

• running a retrieval tool into the wellbore, wherein the retrieval tool includes a self-aligning portion configured to rotate the retrieval tool at least partially circumferentially within the wellbore, an outer diameter portion that is substantially equal to an inner diameter of the wellbore, and an engagement member configured to automatically engage a profile in the whipstock, wherein the whipstock includes a geometry and an angled upper end that prohibits movement of the retrieval tool beyond a depth at which the whipstock is located;
• raising the retrieval tool clear of the whipstock after movement is prohibited due to a geometrical juxtaposition between the retrieval tool and the whipstock, thereby allowing the retrieval tool to freely rotate;
• encountering the whipstock with the retrieval tool, thereby contacting a concave surface of the whipstock only and such that the engagement member is located at an angle offset from an engagement position with the profile in the whipstock;
• maintaining the retrieval tool substantially in alignment with the inner diameter of the wellbore to prevent the engagement member from engaging the window as the retrieval tool encounters the whipstock;
• and
• retrieving the whipstock.