A system is provided for detecting pileup vulnerabilities corresponding to mobile operating system updates. The system includes: an exploit opportunity analyzer, configured to identify pileup exploit opportunities corresponding to a plurality of mobile operating system configurations based on mobile operating system upgrades for each of the plurality of mobile operating system configurations, wherein the identification of exploit opportunities is based on information relating to pileup flaws; a risk database, configured to store information regarding the identified pileup exploit opportunities for a plurality of versions of each of the plurality of mobile operating system configurations; and a scanner application, configured to be executed by a mobile device, configured to query identified exploit opportunities relating to a particular mobile operating system configuration and version, and to evaluate third-party applications installed at the mobile device based on the identified exploit opportunities.