While there, he was able to work with the Spartan C-3 biplane, which Tulsa aviation giant W.G. Skelly used to create the Spartan Aircraft Company 10 years earlier.
After leaving the school, he worked for companies such as Douglas Aircraft and Lockheed Missiles in California before returning to Tulsa to work for North American Aviation, where he stayed until his retirement. He again moved to California where he lived from 1984-2007 before resettling for good in the Tulsa area in 2007.
As he approached his 100th birthday this year, he had one request for his former employer: to fly in the now-defunct company's plane one final time.
On Saturday, 10 days before his birthday, he got his wish.
"I hope people don't have to wait until my age to have as much fun as I'm having," Miller said after disembarking from the recently restored 1920s-era airplane Saturday with pilot Janusz Abczynski. "I hope we can do it again some time soon."
The surprise for Miller was made possible with the help of one of his self-proclaimed best friends: Kim Jones, who until last month was deputy director and curator of the Tulsa Air and Space Museum. The pair met at the museum a few years ago when Miller stopped by for a visit with his son, Henry Jr.
"He had all these photographs and documented all these stories," Jones said. "I refer to him often as the Forrest Gump of aviation because he was always around when things were happening."
"Anyone that went to work at Spartan School of Aeronautics in the 1930s saw an incredible piece of Tulsa aviation history," Jones said. "(Miller) filled in a bit of a gap because a lot about Spartan that has been written is about the war, and Henry was more involved with the day-to-day there."
Neither Jones nor Miller knew before Saturday that school officials at the Spartan College of Aeronautics and Technology had an additional surprise: He received an honorary diploma just before his flight, in front of four generations of his family.
"He obviously picked the best flight school in the country," Spartan College president Peter H. Harris joked during the presentation. "He even paid his entire tuition up front. I'd really, really like it if all of our students showed up and paid all of their tuition up front."
For Miller and his relatives, the diploma represented one of the goals the soon-to-be centenarian said he wished he'd achieved when he was younger.
"Grandpa's just got a lot of history with aerospace here in Tulsa," his grandson Gordon Miller said. "We're fortunate he's able to share a lot of those stories still. We'll sit down and talk and he brings up dates and exact details, and it's like 'Wow. I'm just trying to remember what I did last week.' "
Miller said he was "flattered" by the attention he's received from the voyage.
"I'll never do anything again to equal the pleasure Spartan has given me," he said once the plane touched the ground. "This is the best reception I've ever had in my life."