This paper examines naval procurement challenges for a contrasting set of very small European states. These include a pair of non-NATO navies (those of Ireland and Cyprus) and a trio of very small navies that sit within the NATO alliance, providing for a geographic spread (Iceland, Slovenia and Latvia). Given that the category of small states is intrinsically complex to operationalize (Katzenstein, 2003, p.11) and can include comparatively wealthy states in a global context, who are able to afford modern naval investments, the focus here is deliberately on how resource poor European states are coping with naval procurement. These states have either very limited defence budgets or have suffered recently from severe recessions/austerity, begging the question how they have coped with the challenges of renewing their core capability platforms (vessels, but also potentially aircraft, drones and other resources). Related questions include the impact of the NATO alliance and EU membership. Does NATO facilitate ‘windfall modernization’ through surplus vessel transfers or does it fossilize such small navies with legacy platforms? And how can we explain participation in expeditionary maritime security operations, notably those organized by the EU? To what extent have such far-shore deployments impacted on procurement? This paper offers a number of perhaps counter-intuitive arguments. Firstly, that alliance membership, either of NATO or the EU, may be much less important than is assumed in explaining how and why small states develop their limited naval capabilities. What matters at least as much seems to be the residual salience of national politics and policy-making, together with bi-national relationships. Secondly, there is dearth of strategic thinking evident in how small navies procure vessels and other core equipment. The logic of transferring surplus vessels within a NATO context focused on the Baltic and Black Sea, arguably exacerbates this tendency to procure ‘what is on offer’ rather than what is perhaps more urgent in the face of renewed Russian aggression. As a result, the bulk of Baltics small state naval assets are optimized for mine warfare but less so for littoral warfare in support of land forces. This moreover reveals a critical distinction between such navies is to what extent they anticipate a naval war-fighting role (Latvia, Cyprus) or a softer maritime security conception of operations (Ireland, Iceland). Thirdly, despite their small size and meager resources, their participation in expeditionary maritime security operations has been of value and could produce significant changes in their limited procurement plans, but crucially this again depends on national politics.