Embodiments offer early assessment of upgrade compliance checking upon software landscape production data, prior to actually executing a full impact analysis. In a pre-transport phase, discrete upgrade compliance checks are run and corresponding reports returned to individual developers. In a transport phase, batches of combined compliance checks (bundled into released transports) are run and corresponding reports returned to higher level users. According to certain embodiments, pre-transport and/or transport compliance checking is performed upon landscape production data condensed to a bi-value states. Such condensing can desirably reduce stored data volumes and impart security. According to some embodiments, pre-transport and/or transport compliance checking is performed upon production data merged across multiple landscapes. This avoids storing redundant upgrade check data. Early indication of compliance checking violations, can reduce the incidence of last-minute compliance problems arising during subsequent full impact analysis (which is fraught with potential consequences for system down-time).