When the project first opened to traffic in September 1995, tolls were set at $1.75 each way, but six months later were lowered to $1.00 each way when traffic fell short of projected levels. Despite the toll reduction, revenues did not increase, and the toll rate was increased to $1.15 in July 1997. The Virginia General Assembly also raised the speed limit on the Greenway from 55 to 65 mph.
During this time, revenues on the Dulles Greenway amounted to less than $6 million per year, well below projections, and left TRIP II with inadequate funds to cover its debt service. By late 1997, the company had missed four interest payments and was on the road to bankruptcy. In 1999, TRIP II reached an agreement with its creditors to restructure its debt with $332 million in privately-placed, insured bonds. As part of the restructuring process, the SCC extended the term of TRIP II's concession for an additional 20 years to 2056.
In 2004, TRIP II introduced variable peak and discounted off-peak pricing to manage peak period congestion on the Dulles Greenway. With this user pricing structure, the Greenway became the first highway in the Washington, DC metro area to feature variably priced tolls.
In March 2005, Macquarie Infrastructure Group-an Australian investment bank and toll operator-purchased the Dulles Greenway from TRIP II for $617.5 million. The firm had been actively pursuing the sale for some time. The road was well maintained and MIG was bullish on continued high growth in the region. MIG paid $84.5 million to Kellogg Brown & Root for its 13.3 percent share of the company and $535 million to the Shenandoah Group, which had purchased Autostrade's share in the company and owned the remaining 86.7 percent stake in TRIP II. Ownership of TRIP II is now held in equal shares by Macquarie Atlas Roads and Macquarie Investment Partners I, funds that are both managed by Macquarie Group Limited.
In 2013, the Commonwealth of Virginia considered buying back the Dulles Greenway. The Commonwealth contemplated two options. The first would allow the Commonwealth Transportation Board to issue bonds to fund the Greenway's purchase. The second would create a Dulles Greenway Authority to operate and maintain the facility. The motivation behind the contemplated purchase was to ease upward pressure on toll rates, which had been rising by two-to-three percent annually, and refinance the Greenway's debt at lower interest rates due to the Commonwealth's high credit rating. However, the plans to transfer control did not proceed, because an analysis showed that taking on responsibility for the facility's ownership and operation would not make financial sense to the Commonwealth.
In 2013 and 2015, the Virginia General Assembly proposed implementing distance-based pricing on the Dulles Greenway. However, in September 2015 after a two-year study the SCC ruled that TRIP II did not have to alter its pricing structure. The SCC concluded that TRIP II does not have a monopoly on routes and that it is not a public utility and is subject to competition. It also concluded that lowering the tolls would be unconstitutional, as it could prevent TRIP II from paying its operating costs and debt obligations, which had already been approved by the SCC.