In Australia, consecutive federal governments have acknowledged the contribution of small businesses to the economy, and they have introduced tax concessions to try to assist them. A recent concession that aims to reduce the regulatory compliance encountered by small businesses is the Small Business Restructure Roll-over ('SBRR') relief. The SBRR was touted as providing greater flexibility to small business owners seeking to restructure their business in order to enhance the efficiency of their activities. This article critiques the effectiveness of the SBRR by analysing submissions lodged to the Board of Taxation's Review of small business tax concessions, as well as the findings of a small pilot study with professional advisors. The article seeks to ascertain the level of consistency between the government's stated policy objectives and the perceived application of the SBRR. Generally, advisors perceive the application of SBRR as complex and limited in scope, particularly restricting small businesses' ability to adopt an appropriate structure, which is made more problematic due to the Australian Taxation Office's ruling. Through the observations made, recommendations are proposed in an endeavour to realise the government's policy objectives.