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At time's it's based on pure luck, depending if the oppisite faction isn't paying attention much or not. Your best bet is to zerg with all 10 people in your group and if the oppisite faction takes your flag send about 5-7 people after him. As long as you have a few healers you'll be fine.
I'm not sure if this is still an option or if it was fixed, however, it used to be that if the criteria were met (you do not die and cap all 3 times) you would get the achievement, regardless of who brought the flag to your base and how many times the flag runner died.
you posted on 77 rogue so I will tell you what I did, wait til your 79 and you have the crafted PvP set and then make a premade taking 75+ players. Tell them, you and 1 healer are getting flag and others camp middle and push horde back to gy. I had no trouble getting the achievement with a premade that I made :)
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