The aim of this article is to identify the problems related to information management during the execution of transport orders in micro and small enterprises providing road freight transport services. The article presents the results of qualitative research (in-depth individual interviews with representatives of micro and small transport companies), which are part of the Transportownia.com research project funded by the National Center for Research and Development. The findings indicate that ineffective information exchange between participants in the transport process leads to problems at every stage of the transport order execution, resulting in delays, errors in the registration and planning of orders, problems with loading and unloading, and challenges in the settlement of the order. The research highlights the need for the implementation of modern IT solutions, such as Transport Management Systems (TMS) and cloud technologies, to improve information exchange and optimize transport processes in micro and small road freight transport companies.