The invention provides press brake and press brake tooling technology. Certain embodiments of the invention provide a press brake tool that has an elongated, retractable safety key. In certain embodiments, the invention provides click-in/slide-out press brake tools. In some of these embodiments, the tool has a safety key defining a flat (i.e., a planar wall section/planar surface) that is adapted for sliding along a surface of a tool holder when the tool is dismounted from the holder by moving the tool horizontally out of the holder. In certain embodiments, the flat has a longitudinal length of at least about 0.008 inch (in some cases, at least about 0.010 inch, at least about 0.015 inch, or at least about 0.020 inch), ranging up to the full longitudinal length of the tool. In certain embodiments, the invention provides a press brake tool and a tool holder in combination. Finally, the invention in some embodiments provides methods of press brake operation.