The newspaper industry has clearly been affected thoroughly by digitalization, and as a result has adapted its traditional practices to accommodate for the numerous possibilities this change presents. The printed paper is becoming less viable each day, while its online counterpart continues to gain recognition. In this thesis, we conduct a case study in order to examine a large-scale local newspaper company which has gone from analog to digital and beyond over the course of what is only a fraction of its lifetime. Qualitative interviews are conducted as part of the case study, providing us with valuable insight into both how the organization works and makes decisions as well as the perspectives of individuals. The results are analyzed through applying a theoretical framework, building on previous research regarding digitalization and convergence. The study reveals that post-digitalization technological practices and investment decisions are heavily influenced by a pre-digitalization mindset on many organizational levels, leading to a utilization of new technological services in a manner which leaves much to be desired. Still, the organization competes very well on their market as the printed issue is able to carry its own weight and more. However, sales decline rapidly, and uncertainty combined with excitement clouds the future as the organization are eager to utilize new technology, yet remain divided in opinion on what strategy to adopt when taking on new challenges in an ever more digital context. This hints of many changes to come, with the most intriguing one being what has been identified as a possible change to the very identity of the company.