Hypothetical Case Study

I was given a hypothetical case study and told to read it and understand it. However, I have some questions I was hoping to get answered that I am somewhat confused on.
1) Did the search of Maroon's papers, person, or effects comply with the 4th Amendment? And if so why or if not why?
2) Are any of Maroon's statements admissible? Which ones and why or why not?
3) Does Maroon have to turn over the file, "J-I, 2013-10-24"? Does he have to decrypt it? Why or why not?

Case Study:
Greg Maroon was exhausted. A student at the UC Berkeley Graduate School of Journalism, Maroon had spent the past two weeks working on freelance projects in Indonesia. Having surviving bug bites, a bout of water-borne illness, and a near-miss with a taxi while zipping through Jakarta on one of the region's ubiquitous motor scooters, and having traveled for more than 24 hours to get back to SFO, he was more than ready to be home.

But despite his exhaustion, Maroon was alert. As he shuffled off the Boeing 777 that had taken him almost all the way to his bed, Maroon shifted his backpack and looked around nervously. And he had good reason to be nervous: inside the backpack was a small cage containing a sleepy baby civet which he had nicknamed Rosie. Maroon knew that he faced criminal charges if caught with the small mammal, as the entire species has been banned from importation into the United States since 2004 due to its potential as a vector for Severe Acute Respiratory Syndrome, or SARS.

Maroon also knew that civets are the source of 'Kopi Luwak,' which refers to coffee beans eaten, partially digested and excreted by the animals. While still in Indonesia, Maroon read a recent BBC report about how the high demand for this so-called "cat poo coffee" — a brewed cup costs about $80 — had led producers to shift away from gathering civet scat and toward large-scale farming methods that many consider cruel. And so, having participated in many direct actions as an activist in the Pacific Northwest during his undergraduate days, Maroon decided to chance it.

As Maroon made his way toward the U.S. border with Rosie, however, he panicked, whispered an apology to the still-drowsy little creature, and left her behind a pillar near the gate.

Maroon was sweating and shaking by the time he handed his landing card and passport to U.S. Customs and Border Protection Officer Len Altimeter. When Altimeter asked Maroon several routine questions about his travels, Maroon stammered and looked at the ground. Altimeter also noticed that Maroon had checked both "Yes" and "No" on the landing card box regarding the importation of animals, and that on top of this, he had scribbled out both answers.

Officer Altimeter referred Maroon to a more detailed screening by two other CBP Officers, Edie Hasbreak and Lauren Poitrest. Officers Hasbreak and Poitrest first asked Maroon if he had anything illegal in his luggage. Maroon, petrified, simply looked at the ground. The officers then confiscated Maroon's backpack and began looking through its contents. Upon spotting Maroon's computer, the officers immediately noted that it was plastered with stickers from numerous animal rights organizations, Tor, PGP and — significantly — the Electronic Frontier Foundation, which the officers recognized from news reports showing an identical sticker on a laptop belonging to former NSA contractor Edward Snowden.

Around this time, San Francisco Police Department Sgt. Jake Crawdad stumbled across Rosie. Figuring that CBP would have some idea about what to do with an exotic animal in an international terminal, Sgt. Crawdad took the box containing Rosie to Officer Altimeter, who directed him to the area in which Maroon was being detained by Officers Hasbreak and Poitrest. As soon as Sgt. Crawdad walked up with Rosie, Maroon broke down in tears. (Rosie, meanwhile, broke into a tiny yawn.) Officer Hasbreak gently asked Maroon whether the little civet was his, and he nodded tearfully. She then asked whether he might boot up his laptop for the officers, to which choked out a "No."

The mood in the room shifted palpably. Officer Poitrest suddenly grabbed the laptop and hit the power button to boot it up. The computer started up normally, but when Officer Poitrest tried to click on a file on the desktop that caught her eye — "Central Java interviews with J-I, 2013-10-24" — she was prompted for an encryption password. Officer Poitrest asked for Maroon's password, but he just remained silent. He was subsequently placed under arrest for the illegal importation of a civet and taken to jail.

Given his past activities in Seattle, Maroon was already on the radar of both the FBI and the NSA. Maroon's arrest triggered an alert to Special Agent Andy Security, a Joint Terrorism Task Force investigator with the FBI's San Francisco field office. Special Agent Security called his old friend, Sgt. Crawdad, who relayed the troubling existence of an EFF sticker on Maroon's laptop. Sgt. Crawdad also described what had happened with the Central Java interviews file.

Special Agent Security immediately realized that "J-I" probably referred to Jemaah Islamiyah, the Central Java-based terrorist group likely responsible for bombings in Bali in 2002 and 2005 that killed a combined total of 225 people and injured hundreds more. Special Agent Security then ran a query of Maroon's phone traffic with the NSA, which came up with several "hits" linking Maroon to known terrorists. Recognizing that Maroon might have interviewed J-I members for a journalistic purpose, Special Agent Security put on his nicest phone voice and called Maroon to see if he would cooperate, suggesting that he could make the charges regarding Rosie go away. Maroon declined, and invoked the Fifth Amendment. Special Agent Security then sought a grand jury subpoena for the Central Java file by certifying that it contained information relevant to the FBI's ongoing investigation into Jemaah Islamiyah. The grand jury issued the subpoena, and Special Agent Security served it on Maroon.