The objective of this study was to determine whether overweight insulin resistant individuals who lost weight and improved cardiovascular risk factors during a 4-month lifestyle intervention could sustain these lifestyle changes in the long-term. Seventy-nine insulin resistant adults were randomised to a control group or either a modest or intensive lifestyle intervention group for 4-months. Thereafter the two intervention groups were combined and all participants were followed-up at 8, 12 and 24 months. Anthropometry, blood pressure, fasting glucose, lipids, insulin and aerobic fitness were measured and dietary intake was assessed. An interview was conducted to determine factors which participants perceived facilitated or hindered maintenance of healthy lifestyle habits. Seventy-two (91.1%), sixty-nine (87.3%) and sixty-two (78.5%) participants were retained at 8, 12 and 24-month respectively. At 4-months the adjusted difference in weight between the modest and control groups was -3.4 kg (95% CI -5.4, -1.3) p=0.002 and intensive and control groups was -4.7 kg (-6.9, -2.4) p=0.0001 respectively. At 2-years there were no significant differences for weight when the initial 3 groups were compared or when the combined intervention group was compared with the control group. At 2-years, 64% of participants reported that more frequent follow-up would have helped them to maintain healthy lifestyle habits. Even intensive counselling for 4-months with 4-monthly and then yearly monitoring were not enough for maintaining lifestyle changes sufficient to sustain weight loss. More frequent monitoring for an indefinite period was perceived by two-thirds of participants as necessary for them to maintain their initial lifestyle changes.