Each phase of the deployment cycle poses challenges to military parents and children, with the post-deployment family reintegration period requiring returning military parents to resume such roles as direct caretaking and child discipline. Although veterans often report concerns about this domain of reintegration, existing measures permit only limited assessment of their parenting experiences. The authors initiated development of a self-report checklist to improve such assessment through two pilot studies. In the first, they generated a 30-item checklist of positive and challenging veteran parenting experiences, by interviewing nine clinicians experienced in assessment or intervention with veterans. In the second, 20 male veterans (mean age = 40.5 years) rated each parenting item based on their experiences during post-deployment family reintegration. They also indicated whether they had experienced any of 11 possible personal problems during this period and completed a family functioning measure. Results indicated that checklist items were relevant for the returning parents, that positive parenting experiences were endorsed by a higher percentage of veterans than challenging experiences, and that challenging experiences were associated with several personal problems and poorer family functioning. Further psychometric testing with larger, more representative samples of male and female veterans is needed, to establish the validity and utility of the measure.