The modernization of the Bulgarian railways has been underway for over 20 years. Hundreds of kilometres have been rehabilitated with funds from the European Union. The aim is to join the main Trans-European network, according to Regulation No. 1315/2013 [1] of the EU. Given the complex mountainous relief, the specific engineering objects are now the design and construction of a large number of tunnels (in the Sofia-Plovdiv section alone, over 16 tunnels are planned, the longest of which is 6 km long); the design and construction of railway bridges, some of which have unique dimensions; the rehabilitation of bridges; and the construction of drainage facilities, including drains, ditches, and culverts (some of the culverts have a unique length of about 80 m). The report analyses the main railway projects with a critical analysis of strengths and weaknesses, according to the EU cost-benefit analysis methodology. The analysis presented in this report is unique for Bulgarian railways, as it includes a large volume of projects in the field of designing and building railway infrastructure according to European and world rules, which have not been used in Bulgaria until now. This is only the first stage of scientific research, which involves collecting data, examining the data, and building a working hypothesis. After the completion of the construction (supposedly by around 2029), there will be measurements of the railway and a diagnosis of its condition. At this time, data will be collected again, and the credibility of the presented hypotheses will be verified. The conclusions will serve for the more adequate preparation of the technical assignments for future infrastructure projects in the field of railways.