flyCowboys vs Sheppard Air

Sheppard Air is famous for one thing: getting pilots through FAA writtens fast with a proven memorization system. It is especially popular for the IFR, commercial, and ATP tests. But memorizing answers is not the same as knowing them. Here is an honest comparison for 2026.

Quick Comparison

A side-by-side look at the key differences

Feature	flyCowboys	Sheppard Air
Price	$29.99/mo or $167.99/yr	~$50–$75 per test
Mobile App		Dated
AI Personalization
AI ATC Radio Practice
Flight Logbook Included
Pass Guarantee	100% refund	Money-back
Content Updates	Monthly	Ongoing
Study Method	AI + Active Recall	Rote Memorization
Teaches the Why

Pricing Breakdown

See how the costs compare

RECOMMENDED

flyCowboys

$29.99/mo or $167.99/yr

3-day annual trial included

AI-powered active recall
AI ATC radio practice
Pass guarantee
Cancel anytime

Sheppard Air

~$50–$75 per test

One-time purchase

Traditional study method
No AI radio practice
No AI personalization
Limited content updates

Sheppard Air: Pros & Cons

A fair and balanced look at what Sheppard Air does well and where it falls short

What Sheppard Air Does Well

Memorization system with a long track record of passing scores on FAA writtens
Very popular for IFR, commercial, and ATP knowledge tests
Low one-time price per test compared to full ground school courses
Free phone support from real instructors. Pilots in forums swear by it
Money-back guarantee if you follow their system and do not pass

Where Sheppard Air Falls Short

The method is memorizing answers, not learning the material. It gets you a score, not understanding
You can pass the written and still get caught in the oral, when the DPE asks you to explain your answers
Software and apps feel dated compared to modern study apps
Each rating is a separate purchase, and there is no PPL + IFR bundle
No radio practice, no flight logbook, and no readiness prediction
No adaptive engine. You grind the whole bank instead of drilling your weak areas

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Our Verdict

If you just need a passing score on a written, fast, Sheppard Air works. Thousands of pilots have used it, especially for the ATP. But memorized answer letters are a trap for a student pilot. The oral exam is where rote knowledge falls apart. flyCowboys teaches the why behind every question and drills your weak ACS areas until they hold. It adds AI radio practice and a flight logbook, and one plan covers both PPL and IFR. Memorize less. Understand more. Walk into the oral ready to explain your answers.

Ready to See the Difference?

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See Plans & Pricing

3-day annual trial • Cancel anytime • Pass guarantee included