Despite initial success, the mall was hampered by financial issues through its developer and owner, Zamias Services, Inc. as well as fees and restrictions from the local government.

Zamias Services, Inc. first applied for an Act 250 land use permit to build a mall in Rutland, Vermont in October 1988.

Factors in the delay included acquisition of a federal wetlands permit, and a lack of financing stemming from difficulty in finding investors.

[3] Diamond Run Mall held a ribbon-cutting ceremony and opened its first twelve stores on August 23, 1995.

Alongside J. C. Penney, Sears, and Kmart, the inline stores opened on that day were Barbara Moss clothing store, Gap, County Seat, Claire's, Regis and MasterCuts hair salons, GNC, Olympia Sports, and Sbarro.

The mall's interior decor was themed after the summertime, with various paintings of butterflies, birds, kites, and flowers suspended from the ceiling.

Many of its inline stores had moved to Diamond Run, including National Record Mart, Regis, GNC, Lauriat Books, and Hallmark Cards.

[5] By December 1997, Diamond Run Mall had still not been fully leased, and the city of Rutland had sued Zamias for $100,000 over not paying the first installment of its impact fees.

However, the mall's occupancy remained above the national average, and several new stores opened including a locally-owned restaurant near Old Navy.