A $151 million expansion completed in April 1997 increased the center's total size to 1,225,000 square feet. The new west wing was bounded by Pratt, Charles, Conway, and Howard Streets, connected to the original 1979 building by an enclosed skywalk over Sharp Street. The expansion was meant to position Baltimore for a generation of growth. For about a decade it did, helping the city's tourism industry hit revenues of $5.15 billion by 2013 with 23.9 million visitors. Otakon, the East Asian pop culture convention, was the center's most distinctive tenant - it grew from a few hundred attendees in the late 1990s to 34,211 at its 2013 peak, filling downtown hotels for a long July weekend. The center hosted medical conferences, sports tournaments, and the occasional national political gathering. The 752-room Hilton Baltimore opened on August 2008, connected by skywalk, financed with $301.7 million in public revenue bonds, intended to make the convention center more attractive to large events that needed contiguous hotel rooms.

Otakon announced at the end of its 2013 event that it would relocate to the Walter E. Washington Convention Center in D.C. starting in 2017. The reasons were specific: space, dates, and uncertainty about whether Baltimore would expand its convention center to keep up. Visit Baltimore had to warn Otakon's bid-evaluating team that potential construction could affect their event - a warning that itself helped seal the relocation. In 2016, the convention's final year in Baltimore, attendance had already dropped to 29,113. The Baltimore Sun reported that Otakon was not the only convention departing. At least ten large conventions had left in the previous decade, citing the same combination of size limits and date conflicts. Visit Baltimore CEO Tom Noonan estimated that at least 30 percent of interested citywide conventions - those requiring 1,200 hotel rooms at peak - skipped Baltimore for other cities because of size constraints or unavailable dates. The convention center had become, in the convention industry's blunt phrase, too small to compete.

The proposed responses came in waves. In fall 2010, the Greater Baltimore Committee proposed a $900 million project combining an expanded convention center, a new 18,500-seat arena to replace 1st Mariner Arena, and a 500-room Sheraton hotel. Willard Hackerman, the local construction magnate who owned the Sheraton Inner Harbor, offered in May 2011 to privately finance more than half of the cost. The State of Maryland and Baltimore City approved $2.5 million for initial design in 2012. Then Hackerman died in February 2014, and the project's private financing went with him. A 2016 proposal for a $600 million expansion plus a new hotel got as far as a request for $3 million in seed money for a study, but the request was never formally submitted to Governor Larry Hogan. A 2018 feasibility study concluded that an expansion was feasible and recommended demolishing the 1979 wing and the Sheraton hotel and rebuilding. The 2019 state legislature considered $600 million in financing but stripped it from the final law. By February 2020, a revised cost estimate had ballooned to more than $1.5 billion, and the proposal was scaled back from expansion to mere modernization.

In early 2024 the Maryland General Assembly created the Baltimore Convention and Tourism Redevelopment and Operating Authority Task Force, which began meeting in August 2024. The task force's final report concluded that the previous expansion proposals were infeasible at the $1.6 billion cost estimate, but warned that maintaining the status quo would result in a steady decrease in event activity. The task force made three recommendations: establish a joint governance authority merging Visit Baltimore and the convention center, restructure ownership and financing with a state-city partnership, and create a direct revenue stream to support operations. Baltimore Mayor Brandon Scott included establishing the new oversight authority in his January 2025 legislative priorities. The task force report quoted a 2021 Maryland Stadium Authority study warning that without action, many events would leave the state entirely for Washington, Philadelphia, Boston, or Nashville. The center sits, in 2026, in a slow holding pattern - still functional, still hosting conventions, still slowly losing the events that anchored its first three decades.

During the COVID-19 pandemic, the Baltimore Convention Center served briefly as a 250-bed field hospital, operated jointly by Johns Hopkins Hospital and the University of Maryland Medical Center. Later it was converted into one of Maryland's largest mass vaccination sites, processing tens of thousands of doses per week in 2021 and 2022. The pandemic showed what a flexible convention space can be when conventions are not happening - mass care, mass vaccination, isolation overflow, emergency shelter. When the public health emergency ended, the center returned to its conventional function: trade shows, professional meetings, and the smaller fan conventions that didn't require Otakon-scale floor space. The Convention Center/Pratt Street Light Rail station at the corner of Pratt and Howard provides direct service to BWI Marshall Airport and Baltimore's Penn Station, making the center one of the most transit-accessible large convention venues in the country. What the future holds depends on whether the funding and governance changes proposed in the 2024 task force report can produce, finally, the modernization the building has needed for two decades.