Systems and methods that automatically identify causes of errors during one or more CAD processes, such as while binding external reference drawings to a host drawing and/or batch comparing sets of multiple drawings. In certain examples, a first session of a CAD program can be used to track potential crash occurrences during a second CAD program's processing of a set of drawings and dynamically replace corrupt drawings and/or broken references with blank (proxy) drawings so that the desired process can complete. Whenever the first CAD session detects a potential error event, such as when the second CAD session is interrupted for a particular length of time, the first CAD session can log the error, close the second session, and/or continue the desired process with a new CAD session.