The digital footprint of the project is its integral characteristic, reflecting both the “official” information on the project, unnecessary and any mention of the project including social networks and other Internet resources. An entropy model for assessing the success of a project is proposed. The model covers the content (semantic part), its environment, and the dynamics of implementation. The increase in informational entropy (uncertainty) of the project cannot be estimated as the sum of the increase in entropy associated with each element of the digital footprint. The main reason for this is the synergy inherent in the digital footprint. Separately insignificant elements of a digital footprint of a project of a negative nature, with their significant number and periodic appearance, cause a “snowball” effect, which leads to an increase and exaggeration of small destructive effects of individual digital footprints. Therefore, it makes no sense to consider the increase in information entropy for each element of the digital footprint of the project, but it is necessary to consider the impact of each new element of the digital footprint on the information entropy of the project. Each element of an active digital footprint is formed on time and meets the necessary requirements. The organized formation of a digital footprint promotes order in documentation, timely awareness of risks, the formation of the required level of demand for a project product, and a proactive assessment of success. The digital footprint should also help attract new stakeholders to create a favorable project image and promote the project’s product. The fulfillment of this set of conditions ensures a decrease in entropy and, as a result, the success of the project. Conversely, if active and passive digital traces of a project increase entropy, then the likelihood of project success is reduced.