A system and method for the automated capture and analysis of data associated with a pilot deployment of client migration is provided. In an initial phase, software specified by a migration plan is deployed to a subset of a target set of client machines. Data from users interacting with client machines in the client migration pilot process is monitored and data corresponding to expected functions is captured in real-time. Captured interaction data is subsequently analyzed with respect to a baseline of expected user interactions for said migrated software system, to determine the existence of difficulty in interacting with a new software system. If difficulty is indeed detected, either the migration plan or current service offerings are adjusted to meet users' expectations. Adjustments and modifications made are dependent on whether determined user difficulties are categorized as isolated or widespread. Data captured from multiple client migration engagements is further analyzed for strategic decisions.