The purpose of this study was assessing eSW IT infrastructure projects' monitoring and evaluation practice. There are indications that the existing monitoring and evaluation practice for eSW IT infrastructure projects is problematic. Descriptive research design was used with a qualitative research approach and purposive sampling technique. To meet this objective, primary and secondary qualitative data were collected using interviews, Focus Group Discussions and document analysis. The analysis of the collected data indicated that eSW IT infrastructure projects have encountered different challenges includes less attention to project organizational structure; tackled with late and over budget accomplishment of IT infrastructure projects; less care for cyber security issues; inadequate attention for man power and capacity building; lack of separated monitoring and evaluation department with its own budget and man power; unable to familiar with the newly delivered devices; overlapping of consulting and contracting role; lack of end usersâ€™ supporting system; and absence of communication plan and service level agreement. The study recommends that eSW program office should work for new organizational structure; invest for comprehensive trainings provided by accreditation bodies; plan for monitoring and evaluation; consider M&E in parent organizationâ€™s policies and procedure manuals; sustaining Ethio-telecom's service; resolve the frequent system blackouts, and exercise service level agreement. Addressing cyber security issues is another critical assignment for program office. As far as our review covered, there have been no studies on this topic of the eSW program office so that this research will be useful to program office and may have contribution for further studie