When you update a port and change the layout of all files, you have to check for collisions, *including* collisions with the previous version of the port.
The case I have at hand is amanda, where (recently) the documentation got split off into a separate amanda-doc package. The split occurred when going from 2.4.2.2 to 2.4.5. Accordingly, amanda-doc should have: @conflict amanda-<=2.4.2.2 @conflict amanda-client-<=2.4.2.2 There is a very good reason for that: even though you're not supposed to have packages from different eras on the same machine (well, that could happen to some users), you have to update them at some points, and pkg_add needs accurate conflict information to be able to figure out how to handle the update. I'm going to run a find-all-conflicts on 3.6, 3.7, and current snapshots packages as soon as I've retrieved a full set in order to find similar cases, but this is definitely something to watch out for: whenever you move files around, and end up commenting stuff to avoid conflicts, or similar, keep in mind that you are creating conflicts with older packages, and you have to write them down.