Military operations have not prevented the spread of jihadist insurgency in the Sahel, particularly in Mali. While some Sahelian elites favour dialogue with jihadists, hoping to negotiate political settlements that reduce or end violence, past political settlements have sometimes set the stage for future conflict. This paper analyses past settlements with jihadists in Algeria and the Sahel, distinguishing between “stabilising settlements” that remove fighters from the battlefield versus “delaying settlements” that allow jihadists to accumulate resources and recruits. Even stabilising settlements carry downsides, particularly when they push jihadists into neighbouring states. The paper also analyses recent efforts in Mali to conduct dialogue with two leading jihadists, Iyad ag Ghali and Amadou Kouffa. The paper assesses that these efforts have faltered due to logistical problems and the state’s ambivalence, rather than due to ideological factors. Although renewed dialogue is more likely to fail than succeed, the paper recommends making further attempts.