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drio asks in the suggestion box which is the best way to keep all the packages installed from pkgsrc up to date. I must confess that pkgsrc is quite weak in the updating area when compared to systems such as apt-get or yum. The problem comes from the fact that pkgsrc is a source-based packaging system, meaning that the end user builds packages by himself most of the times. Doing updates from such a system is hard because rebuilds take a long time and have high chances of breaking, leaving your system in an unusable status.