The Outfit

Prototype Jet Destroyed

When you get to level 10, go to the Northwest part of the map, there is a path heading south, if you follow it, it will lead to a jet. Destroy it and achievement unlocked.

When going through this game which I am highly recommending doing is using the Xbox Achievements road map made by CienPR, when you hit each level of the story just hit CTRL+F on the page and type the Mission you are on, and you will find the achievements you need to look out for and how to do them on each mission. There is about 2 each mission, and there aren't any videos which I would be posting if I could find some, but I guess this game isn't popular enough.

Again credit goes to CienPR, good luck and have fun

Road Map:

http://www.xboxachievements.com/game/the-outfit/guide/#

These are the achievements for Mission 10 of the single player campaign:

Mission 10:

Medals (Achievements):
1) V1 Rockets Destroyed
2) Prototype Jet Destroyed

1) You'll get the medal opportunity for this one on the very Southeast of the island (not on the beach). Destroy these three large, dark-colored rockets. Then go to just South east of the motor pool capture point and destroy the final three rockets to achieve this medal.

2) Along the beach on the Southwest, there's a barbed wired fenced-off path to the left, take it and you'll get the medal opportunity. Destroy the red test plane in front of you to achieve the medal. Stealing the enemy tank here is helpful, but regardless, be prepared for a rather strong Axis defense.

Thanks to Messiadbunny for all the help!