This bill would require quarterly payments to contractors under certain contracts with the Department of Homeless Services and the Mayor's Office of Criminal Justice, and establish a pilot program for quarterly payments for other contracts. Beginning July 1, 2027, covered DHS and MOCJ contracts would receive payments of at least 25 percent of the annual contract value at the beginning of each quarter. Beginning July 1, 2029, the Office of Contract Services would select certain contracts over $1 million for a pilot program that would also receive quarterly payments. By December 31, 2028, the Office of Contract Services would submit a report to the Council evaluating the implementation of quarterly payments for DHS and MOCJ contracts. By December 31, 2030, the Office of Contract Services would submit a report evaluating the pilot program, and the Mayor would submit an evaluation and, if appropriate, a plan to make the pilot program permanent. The pilot program would expire on June 30, 2031.