This paper examines the effect of unemployment insurance on the riskiness of occupational choice by postulating a model of job search in which job offers have two characteristics; their wage and their security of tenure. Two versions are considered: a general case in which the unemployment benefit is earnings-related, and a special case in which the benefit is of a flat-rate form. Of particular interest in the paper is the individual's desired trade-off between wage and security of tenure, and how this trade-off is affected by the type of insurance scheme in operation. Perhaps surprisingly, we find that an earnings-related scheme encourages risk-taking behaviour by the poor, and risk-avoiding behaviour by the rich; in contrast, a flat-rate scheme neither encourages nor discourages risk-taking.