Why does America have territories, and why aren’t they governed the same way as states? Despite boasting a total population of around 4 million people, the legal fate of the five inhabited territories of the United States and the constitutional status of their residents have always occupied surprisingly little of the American legal imagination.

However, that might be changing as the Supreme Court considers two cases directly involving Puerto Rico’s self-governing authority and as a number of legal challenges involving the other territories wind up in federal courts. Rulings in these cases may go a long way toward unwinding the complicated, confusing, and often contradictory relationship between the territories and the United States. In the process, they might also unravel some of the imperialist justifications for maintaining the status quo.

Puerto Rico, the largest of the territories by far, is the subject of the bulk of the legal debate. It is also the territory that has most come up against the legal, governmental, and financial limits of its status. The island is in the midst of a decade-long economic contraction, which has led to hundreds of thousands fleeing to the mainland for jobs and opportunities.

Many attribute the crisis to the island’s lack of “statehood,” as either an independent nation or as a state in the United States. “Puerto Rico doesn’t have access to financial instruments available both to states and to sovereign nations,” said Carlos Iván Gorrín Peralta, a professor at the InterAmerican University of Puerto Rico and a territorial-law scholar. “It is in essence in a straight jacket.”

One case in front of the Supreme Court challenges that understanding of Puerto Rico’s lack of sovereignty. Puerto Rico v. Sanchez Valle, which was argued in January, adds a new wrinkle to an old question: Can a person be charged twice for the same crime? Generally, a strong Fifth Amendment protection against double jeopardy makes that answer clear. However, for the purposes of much of constitutional law, the states and the federal government are considered separate, but overlapping, sovereigns, meaning that multiple states and the federal government can charge an individual with the same exact crime.

In a ruling on whether two defendants could be charged with gun possession in the territory after a federal conviction, the highest court in Puerto Rico ruled that the territory does not have its own sovereignty. The government of Puerto Rico appealed on the grounds that its creation of a constitution in 1952, some conflicting congressional statements over the past 50 years, and the gradual evolution of its relationship with the federal government, combine to grant it sovereignty.

“The issue is whether Puerto Rico has some form, vestige, or mirage of sovereignty, despite the fact that the Supreme Court [of Puerto Rico] has felt that it is an unincorporated territory subject to the plenary powers of Congress,” Gorrín Peralta told me.

The executive branch of the government, in an amicus brief, agrees enthusiastically with Puerto Rico’s Supreme Court, noting that Puerto Rico could only have sovereignty if recognized fully as a state or if spun off as an independent country. While Gorrín Peralta believes a 5-4 ruling upholding the rejection of sovereign status or a 4-4 tie reinforcing the lower court’s rejection are the most likely outcomes, such rulings could bolster the already-vibrant pro-statehood movement within the territory. Also, a 4-4 ruling would not set national precedent and would allow a similar challenge––say from another territory––to rise to the federal courts again.

The second case involves a more complicated issue of bankruptcy law. Puerto Rico v. Franklin California Tax-Free Trust, argued last week, involves Puerto Rico’s decision to create mechanisms for its local utilities providers to restructure debts, in a way similar to what Detroit did under Chapter 9 bankruptcy options. In a 1984 revision of bankruptcy code, Puerto Rico was expressly barred from being able to restructure under Chapter 9, but it was granted at least some authority to create its own laws. The question of congressional preemption of Puerto Rico’s laws could again be at play here.

The ruling in Puerto Rico v. Franklin will probably have fewer implications on the sovereignty or potential statehood of Puerto Rico than Puerto Rico v. Sanchez Valle, but it will have sweeping and massive implications on the ability of the island to recover from an economic crisis. And in the aggregate, both cases can help clarify Puerto Rico’s political status, which in some ways looks more like a colony than the self-determining “commonwealth” that the international community has recognized since 1953. The shadow of colonialism is darkened by the amicus briefs in Puerto Rico v. Sanchez Valle, which suggest that Puerto Rico is a property of the United States and that under existing law it could be ceded to another country without any input from the Puerto Rican people.

“The problem with these two cases—perhaps the blessing—is the relationship between Puerto Rico and the United States for the past 60 years has been obscured by ambiguous rhetoric regarding a ‘unique relationship,’” Gorrín Peralta told me. “These two cases, which are authorized by cert by the [Supreme Court] in the same year, seem to emphasize that that ambiguity of 60 years is disappearing.”

But Puerto Rico is not the only territory fighting legal battles over historically fuzzy issues. For many residents of American Samoa, a tiny archipelago and the only U.S. territory in the Southern Hemisphere, the legal questions are even more fundamental. Although people in other territories are considered citizens who cannot vote in national elections by virtue of not living in states, American Samoans are not even considered citizens at all, instead receiving the label of “U.S. National” at birth. This means that American Samoans must become naturalized in order to be eligible to vote in national elections, even if they move to the mainland. However, American Samoans can—and often—do join the military.

Tuaua v. United States, originally filed after its lead plaintiff, Leneuoti Tuaua, was barred from becoming a California police officer because he was not a citizen, raises the issue of birthright citizenship on U.S. soil with respect to American Samoa. The plaintiffs, in 2015 arguments before the District of Columbia Circuit Court, argued that the 14th Amendment extends citizenship to all people born in the United States, including the territories. The court rejected that argument, stating that the nature of birthright citizenship as actually outlined in the Constitution was vague (we’ve seen this fact play out in the presidential candidacy of Senator Ted Cruz, too) and that American Samoan people, who fear intervention by the United States in local affairs, are not entirely in favor of citizenship in the first place. However, after that defeat, the plaintiffs filed a petition for writ of certiorari in the U.S. Supreme Court, and it is possible that one more case on the status and rights of territories could see an argument before the country’s highest court.

One last federal lawsuit concerns the rights of citizens in territories to vote in national elections. Segovia v. Board of Elections Commissioners, filed late last year in the U.S. District Court for the Northern District of Illinois, argues that the equal-protection clause is violated by picking and choosing which American citizens overseas are granted voting rights. This directly targets territories, the plaintiffs argue, in a way inconsistent with the 14th Amendment and with the way territories are administered. The plaintiffs, all residents of Guam, Puerto Rico, and the Virgin Islands, are all former Illinois residents who could at one time vote, simply by virtue of living on the mainland. This case highlights the curiosity of expressly carving out certain territories from full and absentee national-voting rights, another issue that exists in the gray area between colony and self-determination in which the United States seems to have placed its territories.

As Gorrín Peralta notes, “Things have changed in the world.” Puerto Rico may illustrate the outer limits of just what the current relationship between America and its territories can accomplish—and where it falls short. That changing world has been reflected, at least in Puerto Rico, in rising support for statehood, which captured a majority of support on the island for the first time in 2012. The U.S. Virgin Islands, while a much smaller territory, are similarly affected by economic woes, a recession, and debt. Guam and American Samoa contribute a disproportionate share of military recruits but don’t receive veterans assistance commensurate with that effort. Above all, the territories remain underfunded and vulnerable outposts of American influence that are uniquely at the mercy of congressional policy.

Long years after the United States seized these territories in an early 20th-century quasi-imperialist land grab, the nation seems finally to be grappling with the consequences of those actions. These court cases may refocus the debate over what territories and their residents can and cannot do, and on what they mean to the United States. And they return the spotlight back to a decidedly imperfect union, as the justices weigh whether and how to make it somewhat more perfect.