In this thesis, I examined how an automated digital solution could facilitate the user experience within PIM by examining how users acquire, organize, manage, and retrieve their personal information on digital devices using photos and screenshots. I conducted an online survey to validate findings from the literature review and an exploratory contextual study to understand and improve the user experience. Using descriptive statistics and thematic analysis, I discovered specific patterns and indicators of how screenshots and photos are used on PIM. Participants welcomed automatic PIM, but there were few concerns about the automatic deletion and trusting external parties with access to private information. The prototypical solution showed that it should be a personalized, adaptive, and automatic retrieval system.