Walking off with his team, when he's out of earshot: "Is it me or was there something up with him claiming to have been uncontactable? He's a genin, right? I thought genin aren't supposed to be out of contact?"

"That is standard protocol. Something is not right."

"Yeah. And how many genin missions have you not wearing your headband - but willing to talk to Leaf shinobi?"

"He's always set off red flags for me..."

"I do not believe we should trust him."

"Yeah. Think Jiraiya would know if anyone else had a mission around here?"

"He might."

"We should let him know, then. Most of my clones haven't found much else, I don't think..."

"Perhaps by now he has recovered."

"Well, if not, we can figure something out." And possibly make Jiraiya regret his life choices.

Back to the inn, where Jiraiya has migrated over to the main bar and is looking much better, engaging the bartender in a lively trade of stories. (He's drinking water.)

"Hey old man! Feeling human again?" Naruto asks, bouncing over.

"More or less!"

"We did some wandering! Only found out a bit so far, but there's at least one concerning thing?"

"Oh, good. What is it?"

He summarizes the thing with Kabuto, and then mentions the tidbits his clones found, like Tsunade winning big and then not gambling since.

Jiraiya is Not Happy to hear about Kabuto.

"He disappeared just before the Exams," Jiraiya explains. "The top theory is that he defected to Sound."

"We didn't tell him anything incriminating, but it is - very not good if Sound is here. He said he's on a mission, though."

"A mission for Sound, perhaps. That is not good."

"- Could he be looking for Tsunade?"

There's not much else interesting in this town, after all.

"Orochimaru was hurt pretty badly during his fight with Kakashi and the old man," Jiraiya says.

"...And if he thinks only Tsunade can heal him..."

"Then he'd come looking for her, yeah." Jiraiya sighs.

"That could explain the time period of the bet. If he gave her a deadline to make a decision."

He drags a hand down his face. 

"This is a problem, though right now we just have ideas... Do we want to - try talking to Tsunade again? I don't know we'll be able to follow her without her noticing..."