Underinsurance and low financial literacy have been shown to be key issues impacting the effectiveness of personal financial management. Both issues are made more important by the complex financial system, an ever moving array of financial products and services, and the progressive move towards self-reliance in retirement. These factors suggest a greater degree of financial independence and more effective financial decision making is required over the long-term, both of which may be undermined by low financial literacy and underinsurance. Little is known however, about the impact of financial illiteracy on the propensity to seek and retain insurance. Using an interview methodology, we obtained the view of informed and non-informed participants to examine insurance literacy in Australia. We find evidence that insurance literacy of consumers is generally low and exacerbated by factors such as low product knowledge, low trust of providers, low awareness of risk mitigation strategies, and behavioural decision-making biases. These factors can culminate in a perception of low value and subsequent underinsurance. Furthermore this appears to be more acute for personal insurances as opposed to general insurances.