Over the course of a full ministerial career, many pastors will find themselves leaving a troubled situation. When a pastor experiences just such a situation, questions arise regarding preaching. Specifically, what is the substance, nature and form of preaching while leaving a troubled situation? What is the pastor's responsibility when preaching in just such a time of transition? This paper explores how to preach when leaving a difficult situation. Specifically, this paper provides a case study of the author's former parish Grace Lutheran Church, the insights from the ACTS Doctor of Ministry in Preaching program and ten implications for preaching in just such a time. Those ten learnings include: It's hard to preach grace to those who have chosen to break their relationship with you. It's difficult to stay motivated to preach when God's call is nearly complete. I need God's grace for me in my preaching. I need to be aware of my nonverbal cues. Laughter disarms the people. The situation that led to the difficult ending needs to be addressed. Not every matter facing a parish is connected to its difficulties. When leaving the troubled situation, it is important to use a variety of methodologies. When preaching during the difficult ending, the preacher should bless the ministry. The pastor should evaluate their model of ministry when preaching in a difficult ending. The methods used within this paper include the author's preaching joumal, outside verfication based upon a panel interview, literature within the field of preaching and church administration and insights gained from the doctoral program itself.