On a rainy Thursday morning, with less than two weeks until the voter-registration deadline, Bill Cobb was working the waiting room at the Defender Association of Philadelphia for a little-courted pool of voters: people entangled in the criminal justice system. But, even as the rest of the country was fixated on the presidential contest, it was not an easy sell.

"Young lady? Are you registered to vote?" Cobb asked a woman in her 20s waiting to see her court-appointed lawyer. She was. "Are you going to vote in November?" he asked. She was not.

"Apathy is so high," said Cobb, who in 2015 founded a nonprofit called Redeemed that helps support ex-offenders, and this summer started a campaign, #freetovote, that aims to register 20,000 ex-offenders in Philadelphia.

Pennsylvania has among the nation's most progressive voting laws: Virtually anyone who isn't currently incarcerated for a felony conviction can cast a ballot. But getting out that vote - even in a year when Pennsylvania is considered a key battleground - is another matter.

"Traditionally there isn't a significant investment in getting these people out to the polls," Cobb said. "Many of us believe the politicians are not interested in having these people vote, because it makes it difficult to manage the outcome of the election." After all, a committeeman can't hand a sample ballot to an inmate voting absentee from jail.

It's a battle fought piecemeal every presidential election. So, voter education falls to groups like the American Civil Liberties Union and the Pennsylvania Prison Society, as well as correctional authorities. The state Department of Corrections has identified 6,000 inmates (out of 50,000 statewide) who are incarcerated on misdemeanors and therefore are eligible to vote, and counseled them individually on voter registration and absentee voting, a spokeswoman said.

The Philadelphia Department of Prisons, meanwhile, put out a request for proposals for an up-to-$32,000 contract to undertake voter education within the jails, where most of the 7,000 inmates are eligible to vote, as they are awaiting trial or serving misdemeanor sentences.

The department selected a public relations firm, GNCPR, run by Monica Peters, for a contract worth $13,250 and running through the May 2017 primary. Peters, at an hourly rate of $200 for 65 hours, would visit each city facility a few times, to provide voter-registration and absentee-ballot information to 10 to 20 block representatives at a time, who would then relay the information to other inmates.

Although the Department of Prisons provided a general statement that voter education is part of the departmental mission, it did not respond to questions about how many voters were registered, or how Peters was selected over applicants including the Pennsylvania Prison Society, the human services nonprofit JEVS, and the Center for Returning Citizens. Peters, a former freelance contributor to the Inquirer, declined to speak with a reporter.

The Board of City Commissioners, which oversees voter registration and elections, also offered to undertake voter education in the jails at no cost, but was told a contractor would be handling it, according to Tim Dowling, chief deputy to Commissioner Lisa Deeley.

"We'll offer our assistance any time anybody needs it," he said. "We're all over the city, going to students, nursing homes, senior centers, trying to get people engaged and excited about the voting process."

Dowling said the commissioners were unable to track how many voters register from the jails or the number of absentee ballots requested there.

Others who had vied for the contract worried that an opportunity to do meaningful civic engagement work had been lost.

Ann Schwartzman, executive director of the Prison Society, said her group had hoped to leverage funding and their hundreds of volunteers to run voter education workshops with all jail inmates, not just block leaders. They have done what they can from the outside, including a voting rights poster and flier campaign that's wallpapering the Defender Association, probation and parole offices, courthouses, prison visiting rooms, and the buses that shuttle visitors to and from prisons.

That's necessary because misinformation is rampant, said Tom Innes, who chairs the Prison Society's policy committee. Even the state's official VotesPA.com website, which lists 10 acceptable reasons for voting absentee, fails to include incarceration among them.

"People think if they were convicted of a felony, no matter how long ago, they are barred from voting, and that's just not true," Innes said.

He said many are confused because laws about who can vote vary state by state. And in Pennsylvania, the law changed not that long ago: Convicted felons couldn't vote for five years after their release until Commonwealth Court ruled in 2000 that this was unconstitutional.

Also, the county-by-county absentee voting process is opaque.

"I've heard from some in local county jails that it's a difficult feat to complete the process and have the sense that their vote really counted," Schwartzman said.

Jondhi Harrell, who runs the Center for Returning Citizens, sees the estimated 300,000 ex-offenders in Philadelphia as a hugely powerful group of voters - if only they could be engaged.

"Returning citizens do not trust the system. They've been traumatized by the system," he said. "Getting people to see that the political process can benefit them as an individual, as a family, and as a community is extremely difficult."

Harrell applied for the prisons contract because, he said, "it didn't need to only be an informational session. It needed to be an inspirational session."

He added: "How can you give a contract a returning-citizens group is vying for to a public relations firm?" His point was that to engage those voters requires connecting on a different level.

Cobb, who spent six years in state prison in the 1990s, has found one point that usually works when he is talking to voters at the Defender Association, or at expungement clinics: "If you tell them you can elect the DA, that's one of the lines that really seems to get people's attention."

Cobb also wanted to extend #freetovote into the Philadelphia jails as a volunteer. But as of the end of September, he said, he had not yet received approval to do so.

For now, he's not optimistic about the turnout in Philadelphia in November.

"We've registered 7,300 people, and 60 percent have selected no party affiliation. I tell them in Pennsylvania to vote in the primary, you have to choose a party. I've been doing voter registration since I was in high school," said Cobb, 46. "This is unprecedented. I can't believe people don't want to be affiliated with either party."