Ackerman was paid nearly $1 million to walk away from her job.
The Philadelphia School Reform Commission, which approved a buyout of $905,000 plus $83,000 more in unused personal and vacation time, also agreed to allow Ackerman to file for unemployment.
But her attempt to collect more cash drew ire from many, including Mayor Nutter, who in November called the move "astounding" given the district's fiscal crisis.
Now, that crisis is worse.
With just a few months left in the school year, the district must find $60 million more in cuts. That's on top of hundreds of millions in layoffs and deep losses for schools.
Had the unemployment benefit been granted, the district would have been on the hook for that money.
Citing privacy laws, a spokeswoman for the Pennsylvania Department of Labor and Industry said that she could not comment on any individual's unemployment claim.
Ackerman is currently living in Albuquerque, where she now runs an educational consulting firm.
Though she spent more than 40 years as a public schoolteacher, principal and superintendent, Ackerman has said that her difficult experiences in Philadelphia schools have led her to believe that vouchers and charter schools are necessary to save public education.
Ackerman has said that she was forced out of her job by politicians, a claim the mayor and others have strongly denied.
Contact staff writer Kristen Graham at 215-854-5146, firstname.lastname@example.org or on Twitter @newskag. Read her blog, "Philly School Files," at www.philly.com/schoolfiles.