This disclosure describes various tools and associated methods suitable for gaining access to extravascular spaces. The various tools and associated methods utilize a boring tip that may rotate to aid in safely and effectively crossing diaphragmatic attachments. The boring tip may, in some instances not have any sharp edge. For example, the boring tip may have a dome shape but including at least one surface recessed and offset from a summit of the dome shape. Various mechanisms may be used to control rotation of the boring tip as described herein.