We investigate issues that Bluetooth may face in evolving from a simple wire replacement to a large-scale ad hoc networking technology. We do so by examining the efficacy of Bluetooth in establishing a connected topology, which is a basic requirement of any networking technology. We demonstrate that Bluetooth experiences some fundamental algorithmic challenges in accomplishing this seemingly simple task. Specifically, deciding whether there exists at least one connected topology that satisfies the Bluetooth constraints is NP-hard. Several implementation problems also arise due to the internal structure of the Bluetooth protocol stack. All these together degrade the performance of the network, or increase the complexity of operation. Given the availability of efficient substitute technologies, Bluetooth’s use may end up being limited to small ad hoc networks.