In keeping with the Osprey's troubled history, one of them developed mechanical problems and had to return to the Wasp for repairs before resuming its flight, reports CBS News national security correspondent David Martin.
The Marines kept the flight secret because they don't want to draw attention to what is sure to become a trophy target for the enemy.
The Osprey will operate in the wide open spaces of Al Anbar province, where former Marine Bing West says its speed of nearly 300 mile per hour -- twice as fast as a helicopter -- is just what the Marines need.
"The Osprey gives them the opportunity of being any place in Anbar within a half an hour of when they're called out," said West.
But even before it enters combat, the Osprey already has claimed 30 lives in crashes during its development, the worst one killing all 19 Marines on board, Martin adds.
A test pilot who survived a crash had told 60 Minutes his doubts about how well the complex tilt rotor design would ever work.
"It's a part helicopter," said Grady Wilson. "It's a part fixed wing. As such, it will never be an excellent helicopter or an excellent fixed wing."
Former Secretary of Defense Dick Cheney tried to kill the program in 1989, but the Marines persuaded Congress to buy it anyway.
"You've directed me to buy the V-22, a program I don't need," said Cheney.
The crashes and resulting delays drove the cost up to $70 million a copy.
"Now the challenge is going to be, is it going to turn out to have been worth all that political investment as well as financial investment," said West.
If the Osprey survives in Iraq as well as it survived in Washington, it will be a success. If it performs as poorly as it did during its development, it will be a disaster.