The aim of this study was to investigate the sustainability of producing synthetic fuels from biomass using thermochemical processing and different upgrading pathways. Life cycle assessment (LCA) models consisting of biomass collection, transportation, pre-treatment, pyrolysis and upgrading stages were developed. To reveal the environmental impacts associated with greater post-processing to achieve higher quality fuels, six different bio-oil upgrading scenarios were analysed and included esterification, ketonisation, hydrotreating and hydrocracking. Furthermore, to take into account the possible ranges in LCA inventory data, expected, optimistic and pessimistic values for producing and upgrading pyrolysis oils were evaluated. We found that the expected carbon dioxide equivalent emissions could be as high as 6000 gCO/kg of upgraded fuel, which is greater than the emissions arising from the use of diesel fuel. Other environmental impacts occurring from the fuel production process are outlined, such as resource depletion, acidification and eutrophication.