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RTCA/DO-178B Software Considerations in Airborne Systems and Equipment Certification (RTCA Inc., 1992) is a set of considerations or guidelines for the assurance of software in the certification of an aircraft and its systems. The document contains a set of objectives that need to be met and a description of the associated objective evidence required to show that they have been satisfied. The risks associated with attempting and subsequently failing in the certification process can be enormous, and naturally this drives cost and schedule on a given program. Having the skills and tools to assess a third-party organization's ability to develop RTCA/DO-178B compliant software for an aviation project is essential to the success of the project in terms of confidently meeting budget and delivery schedule when outsourcing software development or procuring commercial off the shelf (COTS) software. This is especially true when procuring airborne software from a software organization that does not necessarily have systems development responsibility or responsibility for overall safety of the system on the aircraft. So, can anything useful be learned from industry experience about what contributes to eventual certification success or failure? Due to the nature of their work, a Designated Engineering Representative (DER) often has the advantage of having worked with a variety of software development organizations. In so doing, valuable experience and insight can be gained that is of potential benefit to everyone concerned with outsourcing such software development. The purpose of this paper is to share some of this "practical experience", gained over many years working with various software development organizations on numerous certifiable programs. The objective being to identify a set of useful pointers for anyone considering such an endeavor that will better assure success in certification endeavors.