Mostly, getting this achievement comes down to using Repair Drones a lot until the achievement finally unlocks.
There are a few key notes that when taken into account can make this a bit easier or more understandable why you might be having problems:
* This must be done off a single support, not multiples.
* Drones heal every plane on your team by 10 HP about every 5 seconds.
* The support only lasts about 20 seconds.
* This means it can only heal 40 HP per plane.
* This means to get the achievement you must have at least 3 people all below 70% health and they must survive for 15 seconds.
This could be done through boosting in a custom private game, but to do so you'd need at least 5 people total so boosting is more or less impractical in most cases. As such, your best bet is to use it a lot during 3 vs 3 and 4 vs 4 matches and hoping for the best.