I use a simple optimal stopping model to derive policy relevant insights on the timing of one-shot attacks by small autonomous terrorist units or “lone wolf” individuals. A main insight is that an increase in proactive counterterrorism measures can lead to a short term increase in the number of attempted terrorist attacks because it makes it more risky for existing terrorist units to pursue further development of capabilities. This is consistent with the events in London in 2005 where a terrorist attack on 7 July was followed by a similar but unsuccessful attack two weeks later.