The Boolean modifier needs a manifold mesh to work properly, see the [wiki][1]: > This means that this modifier will only work properly for the > intersection of faces of the two meshes that will result in another > closed loop of edges (filled with faces), creating a new resulting > face topology. Removing the middle section of the cube should fix it: ![enter image description here][2] You may need to recaclulate the normals (<kbd>Ctrl</kbd><kbd>N</kbd>) Also ensure that * The Modifier is applied to the cylinder. * The *Operation* is set to *Difference*: ![enter image description here][3] In addition to the *Knife project* tool mentioned by Haunt_House, You may want to use the Knife tool for this: In edit mode, press <kbd>K</kbd> to start the knife tool and <kbd>C</kbd> to enable *Angle Constrain*. (you may need to hold shift at some points to place a cut, due to the view not being aligned perfectly to the topology) ![enter image description here][4] ![enter image description here][5] [1]: http://wiki.blender.org/index.php/Doc:2.6/Manual/Modifiers/Generate/Booleans [2]: https://i.sstatic.net/vn81C.png [3]: https://i.sstatic.net/GHJLL.png [4]: https://i.sstatic.net/WdFXS.png [5]: https://i.sstatic.net/s41Nt.png