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For the Custom Game achievements (i.e. get 10 wins as zerg vs medium AI opponant in a 1v1, etc etc) do you actually need to grind out a bunch of games vs a medium AI or can you just fight the hardest level AI and have that count for all of them?

After a couple games I've realized it's impossible to loose vs the Medium AI and this has made it boring..

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Good question. I know that beating campaign missions on a harder difficulty gets credit for the lower ones. – Raven Dreamer Oct 16 '10 at 4:14
up vote 4 down vote accepted

Yes. There are several categories in the "Custom Game" achievements where playing on higher difficulties gives you credit for lower ones. I can personally attest to the Outmatched and FFA-vs-7 achievements working, since I beat them all on Insane first and got credit for the easier versions.

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I can confirm this. Winning a custom game against a hard AI as random adds a point to the "win X games against..." achievements for Hard-Random, Hard-(the race you played) and the same for Medium :) – PeterK Oct 16 '10 at 13:43
Yup, winning a game as Random always gives you credit for both a Random win and a (whatever-race-you-played) win. This works for the ladder achievements too. – Brant Oct 17 '10 at 2:16

With Brant's answer said, I've found that completing the Vs AI Kin achievement on Insane does not mean that you get it for Very Hard etc.

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Yes, the kin achievement is different. I actually had a more difficult time gaining that achievement with hard AI than with Insane AI, as the Insane seems to be a bit better at defending against an overwhelming force. – Marcin Oct 29 '10 at 18:17

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