This chapter explores contemporary dynamics in NATO’s deterrence posture in the Baltic Sea Region. Russia has been increasingly probing NATO reactions across the entirety of the Eastern Flank, normalising such incursions as part of its wider strategy of confrontation with NATO. Engaging with the foundations of deterrence theory, specifically the operative concepts of credibility and costly signalling, the chapter argues that neither NATO’s actual deterrence by punishment nor deterrence by denial postures are sufficient to deter Russian hostile intentions. One of the key reasons for this is a false fear of the so-called escalation trap, as escalation in fact deters a revisionist actor such as Russia that does not harbour genuine insecurity. The recommendation for deterring Russia, therefore, is precisely an embrace of escalation – those actions and strategies in both the Eastern Flank and Ukraine that would credibly signal resolve through readiness to accept high costs by building capability and transparent troop deployments.