Although Plone 5 has been released for 2 years, there are still lots of Plone 4.3 sites in the wild. A number of Jazkarta's clients have large, heavily customized Plone 4.3 sites and we have been upgrading them one at a time. As we have gained experience, we have developed strategies for these upgrade projects that minimize risk and spread the work over several mini-projects. In this short talk I will share what we have learned.