Two critical threats to retirement security, insufficient saving and early withdrawal, are usually studied separately. We introduce the concept of "double jeopardy" in retirement decision-making, where individuals both save inadequately and withdraw early, compounding their retirement vulnerability. While retirement savings contribute to long-term financial well-being through security and peace of mind, the complex psychological trade-offs between present needs and future security shape both saving and withdrawal decisions. Recent evidence suggests this is a growing concern: in the US, early withdrawals have significantly reduced the effectiveness of auto-enrollment policies, with an estimated 42% of 401(k) balances withdrawn upon job separation (Choi et al., 2024). Similar patterns emerge globally, from the UK's pension freedom reform resulting in £83.6 billion in flexible withdrawals since 2015, to Chile's experience where Covid-related withdrawals depleted 25% of national retirement assets. Estonia's pension reform also demonstrates the importance of analyzing both regular saving behavior as well as early withdrawal (Reinson, Post, & Uusberg, 2025). These decisions are economically similar (both affect retirement asset accumulation) but psychologically distinct (regular small losses versus one-off large gains) and require different intervention approaches. While automated solutions like default options effectively boost regular saving, they may paradoxically increase withdrawal risk by reducing psychological engagement with retirement planning. We present a systematic framework for understanding these interconnected yet distinct decisions, considering economic, psychological, and ethical dimensions. The framework emphasizes how institutional trust, financial literacy, and socioeconomic factors influence regular versus one-off decisions. This understanding is crucial as more countries consider "pension freedom" reforms, suggesting that policy approaches must evolve beyond traditional economic incentives to address both behavioral challenges simultaneously. Understanding the subjective value trade-offs that drive both decisions is essential for designing policies that enhance overall financial well-being rather than merely maximizing retirement asset accumulation.