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What's the age cutoff for flying in the military? Can an experienced helicopter pilot join the army, Coast Guard... and still fly for them as long as he/she goes through all the basics? What about guard units?
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I actually checked into this a while ago... spoke with an Aviation Recruiter and a commander of an Aviation Brigade.  Standards for acceptance seem to change annually based on how many pilots are leaving and how many pilots the military needs.  That said, you can't be older the 30 (general rule).  There are waivers for age, but it is unlikely (more like impossible) to get one unless there are extenuating circumstances.

 

If you have no military background at all, you'll probably need all your civilian education requirements up front.  If you try to fly for the National Guard or Reserves, their standards are somewhat less demanding.  In all cases, you'll need to be on active duty for WOFT (basic training, warrent officer school, flight school) and possibly the officer basic course.  I have no idea how long that takes... but I'll guess about a year (even if you have thousands of hours - you still have to go).  Then, back part-time if Guard or Reserves.

 

Here's the website for Active and Reserve Warrent Officer's:

http://www.goarmy.com/job/warrant/.  I don't know the website for National Guard information.  You'll have to check the unit in your State.

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I have known people who have been as old as 37 (he was a distinguished combat vet though) get age waivers for WOFT.  It can be done, though it is a function of the needs of the army, and your credentials.  As a current active duty 60 driver, I know that we need pilots, we have been woefully short for years!  If you have a good resume, the first, and most important step is to find a recruiter that will work for you!  They get bonuses for enlisting people, but not for WOFT applicants, ergo, many will try to talk you into enlisting - don't do it!  Shop around for a good recruiter, if he/she won't help you, walk out and go find another one.  The guard and reserves are also a viable option.  They foloow the same regs as active duty, however, unit commanders have a little more flexibility.  They can also be like a "good 'ol boys club", in that, if you know someone, or you take the time to get to know them and they think you are a cool person, you could get hooked up with a flight slot.  Hope this helps.
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As the others have stated, it is really a matter of "the needs of the service" which can change often.  While they all have age limits from as low as 27.5 in the Air Force to the current 32 of the Coast Guard, they are all waiverable if they are short of pilots.  Everybody I know that got a waiver already had all their flying certificates and a Bachelor's degree and could still pass a class one flight physical.  I have seen guys with these qualifications as old as 35 get picked up for the Coast Guard and Army.
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