That urban growth in Australia is uneven in favor of cities than towns is no news. But that the policy for migration to growth centers in regional areas has also not helped should be of interest to policy-makers and planners. This paper aims at articulating the nature of regional urbanization and urban issues in regional cities/towns using the study of Armidale in New South Wales. The findings are based on the lived experiences of migrants that moved to Armidale under the Regional migration schemes and rely on anecdotal information, informal interviews, and analysis of data from government reports and market trends. The town has indicated negative growth in spite of having city like infrastructure and urban demographics. After spending the mandatory time frames all have left the town for a “better quality of life” in metropolitan areas. Besides economic reasons, the non-availability of social and cultural infrastructure that is necessary for their settling is a reason for most to leave such towns and these points to the failure of strategic urbanization. This amounts to secondary migration and thus needs robust planning strategies that respond to the context and for survival of both towns and cities in Australia.