Singapore is apt to be thought of as the proverbial “poisoned shrimp” – a seemingly tempting morsel, but with defences formidable enough to deter those nearby with predatory instincts. The conventional story of the build up of its security in this, the orthodox sense – military might combined with economic success – is well-known. In recent years, however, the leadership has had to confront newer challenges: terrorism, self-radicalisation, and, in recent years, threats relating to disinformation and foreign interference. This calls for a new paradigm in security thinking amongst relevant agencies, and equally, for a new conception of resilience. For when faced with challenges emanating from the grey zone, it is precisely those attributes traditionally linked to Singapore’s strengths (diversity, cosmopolitanism) that can be turned against it by various actors, potentially seeding fissures in the body politic that might be exceedingly difficult to mend.