In 2008, Sweden introduced a policy change to limit the number of days for sickness benefits (SB). This study aimed to elucidate the characteristics of those who reached the maximum entitlement period for receiving sickness benefits (MEPSB) and their future main source of income. Methods: All 5,309,759 individuals, aged 20–63 and residents of Sweden in 2009 were followed from July 2008 to July 2010 regarding SB-days and date of MEPSB and then categorised into three groups: I) no SB-days, II) ongoing SB-days, and III) MEPSB. Mean numbers of SB-days 2.5 years before and 2 years after the policy change and main source of income in 2011 were assessed. Associations between sociodemographic factors, occupation and paid work as main source of income were estimated by odds ratio (OR). Results: A total of 0.7% reached MEPSB in 2010. The mean numbers of SB-days before and after the policy change were higher in the MEPSB group than in the other two groups. In the MEPSB group, 14% had their main source of income from paid work in 2011; this was more common among women born in Sweden (OR = 1.29), people living with a partner and children (women OR = 1.29; men OR = 1.48), and those with occupations representing high educational levels. Conclusions: One out of seven individuals with MEPSB in 2010 had their main source of income from paid work in 2011, although they had a long-term SB before and after the policy change. Further research is warranted to address the long-term effects of this policy change.