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I play primarly sp mode and have noticed that when i colinze the pirate base the game will not reconize this achevment.
Is this a program problem.
Right now some of the achievements aren't working the way they should, Hopefully IC will get on it after the entrenchement release.
"Entrenchement" Will most likely be an Expansion Pack, You will need to Pay for it and Install it Seperatly.
As for the Problem with the Adchivement do you have the Latest Update for the game? I ask because That One came up for me the first time I Played (Installed and Updated right away)
Entrenchment *IS* an expansion pack. Effectively, Ironclad chopped the 'full' expansion into three parts, priced at 1/3rd each.
Frankly, the $10 Entrenchment expansion has more content already than most full $30 ones. It's honestly one of the best real deals I've seen.
Think of it as 'episodic expansion', except unlike Valve, they're not ripping you off completely while wasting their time with a three year wait between each one 
At least for Entrenchment I can confirm that the Pirate Baron Achievement works.
Did it my self yesterday.
Me too
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