When the propeller shaft is out, or the boat is on the hardstand, is the time to pack the stern gland properly. In this video, near the end of Renko's refit, I finish cleaning up and painting the engine bay, install new through-hull fittings and seacocks, then pack the stern gland's stuffing box.

Back on the hardstand a few years later, I try to get the stern gland out to fix it, and install a stern gland greaser, which pushes grease into the packing to keep it lubricated and stop it leaking.