The first part of this chapter analyses the complex interplay between trade, environmental protection and sustainability in the context of the European Union’s (EU) free trade agreements (FTAs). After tracing the evolution of the relationship between international trade rules and the environment, highlighting positive and negative aspects, challenges and opportunities, the article focuses on the integration of sustainable development into EU trade policy, referring to the relevant provisions contained in the Lisbon Treaty and to recent European Commission documents on the topic of international cooperation and in particular trade agreements to achieve sustainable development goals. The contribution then analyses the structure of the chapters dedicated to sustainable development and more specifically to the environment in the so-called new generation FTAs, with a particular focus on the provisions on combating deforestation as a case study. The chapter examines how the EU’s approach to deforestation, through instruments such as FLEGT and the more recent EUDR, is reflected in the specific clauses included in most recent FTAs. The scope of provisions on deforestation in various agreements is briefly analysed, highlighting an evolution towards a broader approach that integrates conservation and sustainable forest management, going beyond the issue of legality of timber trade. The second part of this contribution seeks to examine the labour dimension of sustainable development in modern EU free trade agreements (FTAs). Many of these agreements contain a specific chapter on labour, namely the ‘Trade and Sustainable Development’ (TDS) chapter or entitled more simply ‘Labour’ or ‘Trade and Labour’. This chapter includes labour provisions whereby the parties agree to continue to strive to raise their respective standards and non-regression clauses, aimed at preventing a “race to the bottom” that might lead to a significant deterioration of domestic labour standards. Additionally, these provisions include a reaffirmation of the parties’ existing international commitments regarding labour standards and/or have the aim of incentivising them to commit to key International Labour Organisation (ILO) Conventions. This contribution seeks to critically evaluate the extent to which these labour provisions are an effective way of improving labour standards in domestic legal systems. To meet its intended aim this section focuses on two EU trade agreements with middle-power countries, namely, the United Kingdom (UK) and Japan. These middle-power states constitute an interesting case-study because they still exert influence in the EU and play a significant role in contemporary international relations and global trade. After an overview of EU social conditionality in trade agreements, the contribution undertakes a country-specific analysis, examining the labour provisions of the 2019 EU-Japan Economic Partnership Agreement (EPA) and the 2020 EU-UK Trade and Cooperation Agreement (TCA). On a broader scale, the aim of this chapter is to contribute to the academic discussion about how sustainable development issues are elaborated and included in modern EU FTAs. Relatedly, it also intends to assess the extent to which the provisions of these EU bilateral trade agreements indicate the parties’ intentions in relation to the EU’s role in setting norms for the international trade order.