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For some reason this achievement seems notoriously difficult to trigger, as i often see people complaining they don't get it, and then all of a sudden it pops up.
Make sure you are not offline on Steam, you play the game through Steam, you have the Steam overlay enabled for Medieval Dynasty and you are not blocking anything from EOS or Steam services through firewall/antivirus to get achievements.
It did however work on the Valley, using default settings.
Note that the achievement itself pops at the season roll-over after giving the final (successful) gift, not when the final gift is given, so be sure not to quit early if you think it hasn't worked.
But if his affection is already at 100%, it doesn't really matter anymore.
My first attempt (on Oxbow I think) was over a long period of time, and I was saving/loading, and switching the PC off over a period of days. It failed.
My second attempt (definitely on Oxbow), with one-day seasons and something like 14 gifts, was all done in one straight run. I was saving regularly (as ever), but I do not think I loaded during this period, and I definitely didn't turn the PC off. This also failed.
The third time (on the Valley) which actually worked, I was saving and loading as normal, and did it over a few sessions (i.e. turned the PC off too).
I'm not sure I'd rule anything out at this stage.
It makes it more likely it's not a save/load issue, but it might still be a save/load issue that occurs under certain circumstances and not others.
Some bugs are fiendish. Like trying to isolate the origin of ground loop hum in audio systems is notoriously often awkward, or trying to isolate certain electronic problems with modern cars.
My own theory is that one of the items might not be registering correctly, which would explain the inconsistency and seeming random nature of the issue. It's why I logged the items I used on the successful attempt.
But it's all merely speculation without further investigation.
Nonetheless, for the record, the items I used (that worked) were:
Coverlet, dried figs, flute, jewellery box, needle case, perfume, ring, and thimble.
Mine popped after the cycle of spring/summer/fall/winter/spring/summer/fall/winter/spring (and then talking to her)
Might also be something completely different, since mine triggered a few weeks back after having a similar issue prior to that.