In the last decades, the post-earthquake assessment and strengthening of existing structures are becoming one of the most critical fields of civil engineering. Most parts of Europe, as well as many existing buildings in Croatia, are built in masonry. For that reason, the main objective of this paper is to show the role of updating knowledge in the decision analysis process of existing masonry assessment. Collecting information through condition assessment can be performed on multiple levels with different precision and quality of the obtained data. Several alternative maintenance strategies and corresponding outcomes usually represent decision problems regarding the assessment of existing structures. Regarding existing buildings, decision analysis proved the benefits of updating knowledge in the building post-earthquake assessment process. As case studies, two existing masonry buildings were selected and different assessment procedures and decision scenarios were presented. The Value of Information (VoI) analysis showed that the applied method is feasible from the perspective of owners and users, as its implementation resulted in a reduction in the overall strengthening and maintenance costs.