The first 48 hours of this arrangement produced two lengthy mid-flight gaggles in as many days. But it was also clear that the former secretary of state appears less than entirely comfortable with having dozens of eager reporters in such close quarters, resulting in a handful of exchanges that at times felt as awkward as a blind date.
The first time Clinton walked to the back section of the plane on Monday reserved for press, she said with an enthusiastic smile: "I've been just waiting for this moment."
"I'm thrilled. No, really!" Clinton added, as though to acknowledge the slight irony of her initial comment. "I wanted to welcome you onto the plane. I think it's pretty cool, don't you?"
Unsure of what to say, reporters remained silent.
"You're supposed to say, 'yes!' " Clinton quipped, before talking about Labor Day and the next few weeks of the campaign.
The interaction underscored a reality about the new flying arrangement: Both Clinton and her pack of reporters are out of practice when it comes to casual interactions with each other.
Reporters who have covered Clinton for months witnessed something similar when she launched her campaign in 2015 -- after four years of serving as secretary of state and then taking some time off, it took Clinton a bit to find her footing interacting with press and voters on the campaign trail.
With just more than two months left until Election Day, members of the press have turned up the pressure on the Clinton campaign for the candidate to take more questions from reporters. There is an ongoing count among reporters on the number of days since Clinton's last news conference.
Privately, aides chalk it all up to Clinton being more policy-wonk than political animal, not her lack of familiarity with the press. Clinton herself has said politicking "is not easy for her" and that she is not a "natural politician, in case you haven't noticed, like my husband or President Obama."
Her Republican opponent, meanwhile, has taken a drastically different approach in dealing with the press.
Donald Trump frequently holds press conferences and impromptu gaggles (his traveling press corps still travels on a separate plane). But the businessman also publicly and frequently berates the press, going after reporters (sometimes naming individuals) in stump speeches and even barring some news outlets from his campaign events.
To the surprise of some reporters, Clinton returned to the back of the plane on Tuesday. But she pointed out that it wasn't exactly her decision.
"Good morning everybody, I will come back later. Jen has convinced me I need to," Clinton said in jest, a reference to her spokeswoman, Jennifer Palmieri, who was standing close by.
Clinton chatted casually for a few minutes, telling reporters that she was powering through the allergies that have strained her voice in recent days and even sharing that she had upped her antihistamines. One reporter wanted Clinton's reaction to Trump's campaign manager's comment that Clinton is "allergic to media."
"I said I'm allergic to him, that's what I said," Clinton responded.
After the plane took off Tuesday from Westchester County Airport en route to Tampa, Clinton returned as promised for another gaggle.
"Hey, everybody. We had so much fun yesterday, I think we will do this again," Clinton began. "Adventures on the plane."
Tuesday evening, as the Clinton plane was returning to New York from Florida, the traveling press corps tried its luck at engaging Clinton one more time with a campaign tradition: Rolling an orange with a question written on it down the aisle to the front of the plane.
The question, written with a marker, asked who Clinton would rather have dinner with -- Trump or Russian President Vladimir Putin.
Clinton's traveling press secretary Nick Merrill rolled the orange back, with the word "Putin" circled.
But minutes later, Merrill informed the traveling press corps that Clinton was not responsible for marking the answer -- it was actually Merrill who had circled the orange, and Clinton never indicated her preferred dinner partner.