In the software development industry, it is very common to deviate from the ideal state of enterprise because of various aspects such as miscommunication between different parties, lack of documentation, lack of planning, etc. This deviation is called Enterprise Architecture Debt (EAD) which if not addressed can lead to serious consequences later on. Although, the importance of EAD has been addressed in many research papers before there is still a gap to obtain the severity of EAD in a certain software development system. This is something that needs to be addressed otherwise working without knowing the debt can be disastrous and can cost unaffordable losses. This thesis aims to fill in the gap by providing an approach to measure EA debt and its severity in proportion to the investment portfolio under defined thresholds. This thesis also goes one step further and provides an enterprise-level severity assessment to understand the good and bad investments in more details for better understanding of the EAD in the project.