Two years ago today, the U.S. Department of Education awarded nine states plus the District of Columbia coveted Race to the Top awards in the final round of the $4 billion education-improvement competition.

Overseeing the implementation of the Race to the Top, which has been among President Obama’s signature domestic-policy achievements during his first term, is one of the Education Department’s trickiest and most high-profile jobs. There are probably few people who can attest to this more than the Race to the Top folks in Hawaii, who are trying to get out from under the “high-risk” status label that the federal department bestowed on them last year.

State officials, whom I met with today in Washington before their check-in meeting with the federal department, can tick off a lengthy and on-its-own impressive list of achievements:

• Creating a new program to select, train, and certify turnaround principals and vice-principals for struggling schools (the first cohort is just getting started);
• Expanding a new teacher-evaluation pilot to 82 schools;
• Conducting extensive teacher training statewide on the new evaluation system;
• Building a successful technological infrastructure to support online testing;
• Coordinating professional development aligned with the common-core standards; and
• Coming to a supplemental agreement with the Hawaii State Teachers Association on extended learning time for students in some low-performing schools, including an additional 12 professional development days.

In addition to this progress list, Hawaii was the only Race to the Top state to post gains in reading and math, in both 4th and 8th grades, on last year’s NAEP. And this year, on their state assessments, achievement improved across all subjects and grade levels.

But will any of this matter? There’s still one key thing missing from Hawaii’s Race to the Top portfolio: a new teachers’ contract. A lengthy labor dispute has now entered the mediation phase, and it’s unclear what—if anything—will come from it. What’s needed, according to the promises Hawaii made to secure its $75 million grant, is a new contract so that it can link new teacher evaluations to consequences beginning in the 2014-15 school year.

The scope of work, which outlines key deliverables and milestones for each state, “is really important,” Hawaii state schools superintendent Kathryn Matayoshi told me today. “We have to get the work done well, and done on time.”

Georgia saw a piece of its grant placed on high-risk status after the department saw problems with the state’s teacher-evaluation system.

Hawaii’s entire grant has such status. That’s partly because the teacher-evaluation piece affects at least one other area of its Race grant—its turnaround plans. Incentive pay for turnaround principals is one thing that can’t be accomplished without a contract.

So if the state doesn’t get a new contract, but makes progress everywhere else, what will the federal Education Department do? Will that be good enough to keep its entire grant? Is a new contract all that’s needed to get Hawaii off high-risk status?

And what happens if Obama loses the election to former Massachusetts Gov. Mitt Romney, who will bring in his own education secretary? There will be more than a year left for implementation, so how will a new administration oversee the grants? There are so many questions as Race to the Top hits this two-year mark.