At least one progressive super PAC has jumped into the outside spending battle that’s ramping up in North Carolina’s hotly contested 2nd District, where GOP Rep. George Holding faces a narrowing path to re-election against Democrat Linda Coleman.

WOMEN VOTE!, the independent expenditure arm of the political action committee EMILY’s List, which promotes pro-choice Democratic female candidates for Congress, dropped $406,470 on a new ad attacking Holding for allegedly cozying up to the pharmaceutical industry by giving it a $42 million tax break.

WOMEN VOTE!’s ad contrasts that portrayal of Holding with Coleman, whom the narrator says “grew up working the Carolina tobacco fields” and has been a teacher.

The progressive group’s ad follows more than $1 million in outside spending in the district from the super PAC aligned with Speaker Paul D. Ryan, Congressional Leadership Fund.

CLF opened a field office in August in the 2nd District, where it has reserved $1.4 million to support Holding, who is bidding for a fourth term.

A new ad from CLF released earlier this week claims that Coleman has missed the deadline for paying her taxes “over 60 times.”

“She didn’t pay her taxes on time, but had no problem raising your taxes,” the narrator says.

A Roll Call review of Coleman’s property tax records found that since the mid-1990s, she missed the initial deadline to pay taxes on four different properties on at least 63 occasions.

CLF’s ad does not mention that in North Carolina there is often a grace period ranging from several weeks to several months after the initial deadline for residents to pay their property taxes without accruing interest — rendering the original deadline a “soft” deadline.

Coleman incurred interest on eight different property tax payments after she missed the grace period window in 2007, 2008, 2009, 2010, and 2014.

Her interest bills from those years total less than $500.

Both ads are playing in the Raleigh media market on broadcast and cable.

Holding won re-election by 13 points in 2016 after the district was redrawn. He outperformed President Donald Trump, who carried the district by 6 points.

Recent polling from both sides has shown a close race.

A late-August internal poll for Coleman, conducted by Greenberg Quinlan Rosner Research, gave her a 1-point edge, 45 percent to 44 percent. On Aug. 20, Holding’s campaign sent out fundraising emails raising the alarm about a poll it had conducted showing the congressman down by 3 points.

Inside Elections with Nathan L. Gonzales rates the race Tilts Republican.