Singapore remains one of the few countries with universal male conscription, known as National Service (NS). Yet, while mandated to serve, young queer Singaporeans continue to face institutional and social challenges – in the form of restrictions on their military roles and medical classification, and a heteronormative, toxic masculine environment. Prior research has documented the hegemonic masculine culture of NS that others LGBTQ identities, but little is known about how queer men themselves make sense of their experiences. My study addresses this gap by asking: how do gay, bisexual, and queer (GBQ) Singaporean men navigate their NS experiences, and why do they vary in their disclosure decisions? To answer this, I draw on 15 in-depth, semi-structured interviews conducted in 2024 with GBQ Singaporean men aged 21–35 who have completed NS. While prior research on queer individuals in the military has largely focused on either external discriminatory structures or individual coping strategies, I bridge this divide by arguing that disclosure decisions in NS emerged through a two-way, dynamic interplay between individual predispositions to conceal or reveal when respondents first entered NS, and unique external situations they each engaged with during NS. This interaction produced two distinct criteria of judgment for disclosure: respondents predisposed to reveal focused on safety, while those predisposed to conceal focused on convenience. Through my findings, I show how predispositions, judgments, and disclosure acts are situated, mutually shaped, and constantly evolving. My insights call for future research on queer identity management to look beyond static factors and attend to the complex interactions between individuals and their social environments that shape their actions. More importantly, my story gives voice to a group whose lived experiences are often deemed too socially divisive to advocate for in Singapore. It complicates prevailing accounts of queer experiences in NS, and paints a possibility of what NS can be – a space where queer individuals can proudly serve their country without having to hide their authentic selves.