Recent progress in engineering microvascular networks in vitro and in vivo offers exciting opportunities to create tissue constructs with preformed blood vessels, which are rapidly blood perfused by developing interconnections to the preexisting blood vessels of the host tissue after implantation. This process, termed as inosculation, is well known from the revascularization of various tissue grafts, such as transplanted skin, nerves, or bone. It is characterized by the close interaction of the implant's preformed microvascular network and the host microvasculature. The sprouting angiogenic activity of both counterparts determines whether inosculation takes place internally within the implant or externally within the surrounding host tissue. Successful inosculation involves vascular remodeling as well as infiltration of inflammatory cells and stem cells. With the use of sophisticated in vitro and in vivo models, more detailed analysis of regulatory mechanisms of inosculation will help to develop novel strategies, aiming at further accelerating the establishment of a life-sustaining blood supply to implanted tissue constructs.