BioChoice lignin (BCL) is a newly commercialized pine kraft lignin from Plymouth Mill of Domtar, which is precipitated from black liquor of bleachable-grade pulp. Indulin AT is a pine kraft lignin commercialized by Meadwestvaco for the past 60 years, which is precipitated from black liquor of linerboard-grade pulp. Thus, the two technical lignins are produced under quite different conditions in terms of alkali charge and pulping time/temperature. While the chemical structure of Indulin AT is well documented, that of BCL is totally unknown. In this study, chemical structures of BCL and Indulin AT are characterized using modern analytical techniques and compared with those of pine milled wood lignin (MWL) in order to elucidate the structural changes that occur during kraft pulping and the structural differences, if any, between BCL and Indulin AT. Both BCL and Indulin AT are structurally very different from the native lignin (MWL) in wood, indicating drastic structural modification during the kraft pulping process. Surprisingly, BCL and Indulin AT are structurally very similar, in spite of the fact that they are produced under different process conditions. However, there are subtle structural differences between BCL and Indulin AT. BCL has higher phenolic hydroxyl, catechol, enol ether, and stilbene contents, but lower methoxyl and β-O-4 contents. These differences are explained by the different pulping conditions under which the two technical lignins are produced.