June Risk Barometer

CUBA | UKRAINE & RUSSIA | Southeast Asia

In Global Guardian's monthly Risk Barometer, our Intelligence Team highlights current global hotspots with the potential to impact your business operations and travel. Read below for analysis on the threats we are closely monitoring this month and click here to subscribe for regular intelligence updates.

Cuba Pressure Campaign Nears Moment of Action

Over the past 16 months, the Trump administration has executed a multi-front pressure campaign against Cuba—layering sanctions, energy blockades, and criminal indictments—that now represents the most intensive U.S. coercive effort against Havana since the Cold War. The pressure campaign closely mirrors the one conducted against Venezuela, but Cuba's distinct regional symbolism among many Latin Americans risks broader consequences for U.S. firms and travelers across the region. The lack of a Cuban Delcy Rodríguez equivalent, a high-ranking official with an interest in defecting, necessitates a more complete, protracted conflict to force political change. This protracted conflict could result in disruptions in the Caribbean, including shipping through the Florida Straits.

Recommendations

• Organizations operating in Latin America should monitor for demonstrations or protests that may target U.S. businesses in retaliation for U.S. policy.
• Organizations should develop contingency plans for disruptions to Caribbean maritime traffic in the event of a protracted military operation against the Cuban government.
  

Situation Report

• The Trump administration has advanced its Cuba pressure campaign through four sequenced instruments since January 2025: redesignation of Cuba as a State Sponsor of Terrorism, cascading economic sanctions including the personal sanctioning of incumbent President Miguel Díaz-Canel, energy interdiction targeting fuel suppliers and tanker operators, and the criminal indictment of former President Raúl Castro. Each measure has built on the last, progressively compressing Havana's diplomatic and economic room for maneuver. The campaign structurally mirrors the coercive strategy applied to Venezuela between 2019 and 2026.
• On 20 May 2026, a U.S. federal court indicted former Cuban President Raúl Castro on charges of conspiracy to murder U.S. nationals and four counts of murder in connection with the 1996 shootdown of two civilian aircraft operated by the Cuban American humanitarian organization Brothers to the Rescue. Two weeks later, on 04 June, the U.S. Treasury Department imposed sanctions on Cuban President Miguel Díaz-Canel, his wife, and three others.
• Cuba is experiencing an acute, island-wide energy crisis resulting from the disruption of Venezuelan oil shipments following the arrest of Venezuelan leader Nicolas Maduro. Rolling blackouts of 16 to 20 hours per day are reported across Havana, Santiago de Cuba, Holguín, and other population centers, degrading power to hospitals, water treatment facilities, and telecommunications infrastructure.
• Havana has not publicly signaled any willingness to negotiate. No Cuban government concessions or outreach to U.S. interlocutors have been reported.

Analysis

The sequencing of American actions since January 2025 reflects a coercive campaign with a defined end state of political and economic reform, not a normalization of relations.

The Venezuela parallel is central to understanding the timeline for U.S. objectives and kinetic action. The 2020 indictment of President Nicolas Maduro provided the legal framework and pretext for the eventual arrest of Maduro in January 2026. The Trump administration’s Cuba policy is now replicating that instrument against Cuban leader Raúl Castro. The Castro indictment comes as Cuba’s government faces structural vulnerabilities that are, in several respects, more acute than Venezuela's were in 2025. Cuba has no viable alternative to Venezuelan oil supplies, its foreign exchange reserves are effectively exhausted, and the military conglomerate GAESA, which oversees an estimated 60 percent of the island's economy, has also been directly sanctioned.

The U.S.-orchestrated leadership swap in Venezuela was facilitated by Maduro’s Vice President Delcy Rodríguez, a regime insider willing to work with the United States. The absence of such a figure in Cuba would likely increase instability following any U.S.-led removal of Cuban government leadership.

A further distinction from the Venezuela precedent is how a comparable operation against Cuba would likely be received across Latin America. Maduro's removal generated little condemnation from regional governments or populations. In fact, in much of Latin America it was met with active approval. This result is attributable to the widespread regional disapproval of the Maduro regime, which caused the largest displacement crisis in the Western Hemisphere.

No comparable dynamic exists for Cuba. Cuban emigrants have been absorbed primarily by the U.S. rather than dispersed across Latin America, limiting their effect on regional opinion. Cuba also retains its symbolic standing among Latin American publics as a small nation resisting U.S. pressure and the final holdout of Latin American left-wing revolutions of the 20^th century.

Timeline

• 20 January 2025: President Trump redesignates Cuba as a State Sponsor of Terrorism; the State Department reissues the Cuba Restricted List with over 200 new entity additions.
• 30 June 2025: President Trump reimposes strict U.S. tourism restrictions and financial transaction limits with Cuban military entities.
• 03 January 2026: Venezuelan oil shipments to Cuba stop following Maduro's capture.
• 29 January 2026: President Trump signs Executive Order 14380, declaring a national emergency and establishing tariff mechanisms against countries supplying oil to Cuba.
• 01 May 2026: President Trump signs Executive Order 14404, imposing broad new sectoral sanctions and secondary sanctions exposure for foreign financial institutions.
• 07 May 2026: The U.S. Department of State issues its first EO 14404 designations, sanctioning GAESA and affiliated individuals.
• 18 May 2026: The U.S. Department of the Treasury sanctions Cuban Ministers of Communications, Energy, and Justice.
• 20 May 2026: A U.S. federal court indicts Raúl Castro on conspiracy and murder charges.
• 04 June 2026: The U.S. Department of the Treasury imposes sanctions on Cuban President Miguel Díaz-Canel, his wife, and three others.

Looking Forward

The pressure campaign will very likely continue to intensify in the near term. The Trump administration has escalated consistently despite the absence of Cuban concessions. A negotiated political transition is unlikely given the lack of a domestic Cuban opposition movement. Direct U.S. action modeled on the Maduro capture is also unlikely in the near term but cannot be dismissed over the medium term if sustained pressure fails to produce negotiated results.

Russia–Ukraine War Enters Volatile New Phase

The Russia–Ukraine war has entered a volatile and unpredictable phase, with materially elevated risks to travelers, expatriates, and organizations operating across the region. The Russian Spring offensive has stalled, Ukrainian long-range strikes are intensifying and expanding deeper into Russia, and Moscow has failed to achieve the battlefield breakthroughs it promised. Frustrated by these developments, Moscow conducted two major mass-casualty strikes on Kyiv within ten days—on 23–24 May and 01–02 June—with Russia explicitly declaring a campaign of “systematic strikes” against the city and warning foreign nationals to evacuate. Russia’s shift to targeting central Kyiv increases risk to travelers throughout the area, including at hotels commonly used by foreign travelers.

Recommendations

• Global Guardian recommends against non-essential travel to Ukraine and to Russia for citizens of NATO member states
• For essential travel to Kyiv, Ukraine, consider hotels outside of central Kyiv.

Situation Report

• Ukraine's deep-strike drone campaign has expanded far into Russian territory. UAV strikes on Russian soil increased 250% in the first quarter of 2026 compared to the same period in 2025. In April, Ukrainian UAVs struck Yekaterinburg—capital of the Urals federal district, roughly 1,400 kilometers from the front—for the first time, damaging a high-rise apartment building.
• Russia lost net territory during April and May 2026 for the first time since the summer of 2024 and early estimates suggest that in May, Ukraine gained more territory than Russia did in absolute terms.
• On 23–24 May, following a Ukrainian deep strike on a claimed Russian drone technology headquarters in Luhansk Oblast, Russian forces launched 90 missiles and 600 drones against Ukraine—including 36 ballistic missiles and at least one Oreshnik intermediate-range ballistic missile (IRBM)—primarily targeting the city of Kyiv and the wider Kyiv Oblast. The attack killed at least four and injured over 100 people, with Kyiv's mayor reporting impacts "in every district of the city." Critically, the strike expanded targeting to central Kyiv’s Podil district—a pedestrianized area dense with hospitality businesses and frequented by foreign residents, journalists, and the international community—which suffered heavy damage.
• On 25 May, Russia's Foreign Ministry formally declared that Russian forces were beginning "systematic strikes" on Kyiv's military-industrial targets, warning all foreign nationals—including embassy personnel and international organization staff—to leave the city.
• On 01–02 June, Russian forces conducted a second major strike package against Ukraine—73 missiles, including 33 Iskander-M ballistic missiles, and 656 one-way attack drones—killing at least 22 civilians and wounding 138. Kyiv, Dnipro, Kharkiv, Zaporizhzhia, and Poltava were all struck. Cluster munitions were reportedly used in Dnipro, and Russian forces conducted a deliberate double-tap strike that killed a rescue worker responding to the initial attack.
• On 03 June, Ukrainian forces conducted long-range strikes against the St. Petersburg Oil Terminal and Kronstadt Naval Base—approximately 1,100 kilometers from Ukraine's border—deliberately timed to coincide with the opening of the 2026 St. Petersburg International Economic Forum (SPIEF), a flagship symbol of Russian economic resilience attended by 20,000 participants from over 100 countries. Attendees arriving at the forum reportedly saw smoke rising from the oil terminal in the distance.

Analysis

Since Russia’s initial push to occupy Kyiv and install a Russia-friendly government was halted in April 2022, Russia’s theory of victory has revolved around convincing both Kyiv and Ukraine’s Western benefactors that time was on Russia’s side. Under this theory, Russia can absorb heavy losses to make incremental territorial gains in an attritional contest. However, for the first time in this conflict, it appears that Russia is no longer making incremental gains and is being attritted more than Ukraine. In March 2026, Ukraine launched more one-way attack drones into Russia than Russia launched into Ukraine, with the disparity continuing to grow. In May 2026, the Russian Ministry of Defense claims it downed 9,418 Ukrainian drones (implying even more drones were launched) while Russia launched only 8,150 into Ukraine during the same period.

President Putin faces a compounding strategic dilemma. Ukraine's asymmetric campaign—combining deep drone strikes and tactical counteroffensives—is eroding Russia's ability to sustain offensive operations while simultaneously dismantling the Kremlin's domestic narrative that the war is a geographically contained "special military operation" with no consequences for ordinary Russians.

More frequent Ukrainian drone strikes on Moscow and St. Petersburg are fueling an increasing sense of war-weariness. Public support for peace negotiations has grown from 35% in February 2025 to 59% in February 2026. In an implicit admission of a capability gap, Russia’s legislature (Duma) passed a bill requiring banks to install and pay for electronic drone‑jamming systems on their premises, and allowing selected staff to help counter incoming drones. Putin's response to domestic pressure is to escalate Russia’s strategic bombardment campaign, manufacturing a narrative of strength through intensified strikes.

Looking Forward

The war has entered a phase in which Russian escalation and Ukrainian deep strikes are in a reinforcing cycle, with each side's actions providing political and operational justification for the other's next move.

In the near term, large-scale Russian strike packages against Kyiv in direct retaliation for recent Ukrainian attacks are likely.

In the medium-to-long term, the prospects of an armistice are advancing. While high oil prices and U.S. sanctions waivers offer an economic buffer for Moscow, Russia’s Central Bank has already warned that Russia’s war spending is unsustainable. The more pressure Ukraine can put on Russia with small battlefield advances and continued deep strikes, the more likely that Russia will be to seriously consider a ceasefire.

Southeast Asia Stabilizes After Hormuz Shock—Long-Term Risks Persist

Southeast Asia has weathered the acute fuel disruption triggered by the closure of the Strait of Hormuz (the narrow waterway connecting the Persian Gulf to global oil markets) without incurring substantial civil unrest. Governments in Southeast Asia deployed a mix of fuel subsidies and price caps to suppress consumer-level inflation and dampen the potential for broader civil unrest. The relatively small-scale protests that did occur in the Philippines, Indonesia, and elsewhere have largely subsided, and regional equity markets have partially recovered from their post-closure lows. The near-term risk of large-scale fuel-driven civil disorder is now low to moderate. However, the region remains exposed to medium- and long-term destabilization as socioeconomic vulnerabilities compound.

Recommendations

• Firms with assets and personnel in Southeast Asia should monitor political and diplomatic developments in the region, particularly as they pertain to budget cuts.
• Global Guardian recommends creating contingency plans to be triggered by fuel subsidy cuts, as these could rapidly lead to civil unrest.
• We recommend assessing any private fuel reserves and transportation protocols ahead of the projected Super El Niño this fall.

Situation Report

• Fuel prices across Southeast Asia spiked sharply in the weeks following the 28 February 2026 onset of the Middle East crisis, straining household budgets and triggering protests in several urban centers, most notably in the Philippines and Indonesia. Emergency drawdowns of strategic petroleum reserves, combined with expedited LNG spot purchases routed through alternative corridors, eased the immediate supply crunch.
• Regional air travel also fared better than initially predicted as refineries in Nigeria, the U.S., India, and Europe sharply increased jet fuel production as a proportion of refining capacity.
• Continued high fuel-subsidization rates, energy-saving policy measures, and rapid acquisition of alternative fuel sources in Southeast Asia have insulated consumers from the worst of the energy shock, but are straining state budgets. The ASEAN Summit in early May 2026 failed to produce binding institutional structures that could underpin regional energy resilience.
• The impending Super El Niño—which will bring higher-than-average temperatures and drought to Southeast Asia—will simultaneously stress the region’s fishing and agricultural industries while depressing hydroelectric output and increasing energy demand for air conditioning. With the Strait of Hormuz unlikely to reopen in the near term, Southeast Asia faces financial, energy, and climate pressures that will be difficult to address in the absence of a more unified regional approach.

Analysis

Despite the apparent stabilization, the ASEAN Summit from 06 to 08 May produced only non-binding declarations or bilateral agreements on energy cooperation. This left each member state to manage supply security essentially on its own—the same structural gap that amplified the initial shock. The absence of a binding regional strategic reserve-sharing framework means that any future supply disruption will once again force individual governments into costly, competitive spot-market bidding.

Compounding the risk of destabilization, early indicators point to a developing Super El Niño event that, if it follows historical patterns, will significantly reduce hydroelectric output across mainland Southeast Asia and the Indonesian archipelago. This will push power generation costs higher precisely as air conditioning demand increases and imported fuel supplies remain at their costliest. Agricultural yields and coastal fishing—both critical income sources for the region's rural poor—face lower productivity due to Super El Niño-associated droughts. Taken together, the energy and climate dynamics create a scenario in which governments already burdened by crisis-response spending may face renewed public discontent with depleted fiscal buffers and little regional support.

Looking Forward

If the Super El Niño intensifies as projected, hydroelectric shortfalls could begin to affect grid reliability throughout the region in the fall of 2026 and winter of 2026–2027. Higher electricity prices would compound still-elevated fuel costs, squeezing manufacturing competitiveness and household disposable income simultaneously. The Super El Niño in 1997 has been estimated to have cost global GDP roughly 5.7 trillion USD in lost growth. States in the region absorbed the most recent energy shock through financial measures that will be further strained if the coming Super El Niño generates similar costs.

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