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So, i've done a new pirate start, and I've gotten 3 or 4 different pilots to dump cargo, but I can't seem to trigger this achievement. Does anyone have any tips for getting this to trigger? Does it have to be done over comms, like a request to surrender?

... from this STEAM-Guide:
"A Pirate's Life for Me: Intimidate a pilot into dropping some of their cargo 5.0
Use the "drop your cargo" dialogue option after scanning a ship, if the ship complies (ships with crew with lower morale are more likely to comply) the achievement will unlock"

I unlocked this achievement in the first mission for ACE in the CUR-plot (where you relieve a HighTech-Trader of its cargo). If I remember it correctly, I had not fired one shot (but ACE did of course) and as soon as I asked for the cargo (coms-dialogue) the cargo and the achievement droped...

Ill try that, thanks.

Landed here after searching how to get this achievement.
I did the pirate plot and did not get that achievement during the tutorial mission with Ace.
I then tried to "intimidate" traders by shooting them a bit before asking them to drop their cargo (nothing is that easy, right?).
They would usually not reply and I had some that would just eject their cargo when shot.

The only thing needed is to keep scanning and asking to drop cargo, no shooting.
Eventually, a scared pilot will eject its cargo after asking and will unlock the achievement.