The oncoming retirement of baby boomers has governments worried. Will individual baby boomers demonstrate the ability to prepare financially for their retirement? Well-being in retirement depends largely on financial preparedness during working life. Those baby boomers who are the most vulnerable at the end of their working lives are more likely to become vulnerable during retirement. This study looks at the income of the first baby boomers, those born between 1946 and 1956, aged 50 to 60, according to the 2006 Canadian census. First we establish the socio-economic categories for which members are most financially vulnerable. Then, we estimate how many baby boomers are vulnerable and to what extent. This study’s preferred approach is an interprovincial comparison between Quebec and Ontario, used to analyze individual aspects of baby boomers’ financial positions.