MOODLE_14_STABLE only gets bug fixes (no new features) and those should always be merged to the HEAD/trunk. There should very rarely be a need to merge the other way.
Secondly, after merging a bug fix from the MOODLE_14_STABLE branch to HEAD/trunk, by doing this (in a HEAD checkout):
cvs -q update -kk -j MOODLE_14_MERGED -j MOODLE_14_STABLE [files...]
you need to move the MOODLE_14_MERGED tag for those files on the STABLE branch as follows (in a STABLE checkout):
cvs tag -F MOODLE_14_MERGED [files...]
The full process is described in our CVS documentation ...
General developer forum
List of unmerged files updated...
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