While an ongoing scarcity of foreign exchange (forex) poses a challenge for the sector, macroeconomic conditions are expected to continue to recover, which bodes well for the industry. Though penetration levels remain low, Trinidad and Tobago exhibits strong growth potential, with a comparatively wealthy population and rising demand for health and life insurance products. Moreover, improvements to the regulatory framework, notably the Insurance Act of 2018, appear set to ease business operations and increase consumer confidence. With recovery setting in, downward pressure on premiums may ease; however, industry stakeholders will need to keep costs down and preserve competitiveness to take full advantage of the opportunities to expand market share. This chapter features an interview with Jacqueline Quamina, Chairman, National Insurance Board.