Reddit’s been through a hell of a ride lately. It started with an update to the site’s offensive content policy in May which led several weeks later to the banning of five hate-themed forums, a.k.a. subreddits. Over the Fourth of July holiday, the site largely went dark in a coordinated action by many of Reddit’s volunteer moderators to protest the firing of a popular company employee. Interim CEO Ellen Pao stepped down days later following withering criticism from some quarters of the site—what she would later call "one of the largest trolling attacks in history."

Into the fray stepped Reddit co-founder and newly appointed CEO Steve Huffman to clarify and elaborate on the the site's offensive content policy and take questions from the site's users. Whether it was the company’s intention or not, Huffman's AMA—Reddit-speak for "Ask Me Anything"—will likely mark a signal moment for Reddit's future. In updating its policy on offensive content, Reddit finally admitted it has a problem with harassment—in sharp contrast to its notoriously hands-off attitude in the past pegged to a rigid definition of "free speech." In admitting it has a problem, Reddit has set itself the unenviable task of trying to fix it. Its success—or failure—will likely serve as a model (or cautionary example) for solving some of the most pervasive problems on the Internet.

Reddit’s effort to curb its dark side without betraying its ideals becomes an emblematic drama of the Internet today.

Reddit’s conundrum is worth following not just because the site is one of the major anchors of the social web or because it attracts massive amounts of traffic—a whopping 164 million visitors each month. It’s important because the site is founded on principles that mirror the founding principles of the web itself. Reddit was conceived as an open forum, a place where conversation is self-regulated and community-driven, freedom of expression is prized above all, and authorities don't meddle with—much less censor—content. And sometimes, wonderful things happen. But there’s also a dark side. Trolls and harassment abound, and users revel in despicable topics. At least 46 active subreddits are devoted to white supremacy, according to the Southern Poverty Law Center. Misogynistic content also abounds.

And so Reddit’s effort to curb its dark side without betraying its ideals becomes an emblematic drama of the Internet today. Calls for rooting out online harassment have never been louder the more central social platforms become to everyone's daily life. But no one has come up with a great answer for how to do it. Outsourcing content moderation to an army of laborers, typically overseas, often at an enormous mental and emotional toll? Automating the process through artificial intelligence? Is it possible at all without violating the personal freedoms that make the Internet so empowering to so many? Solving some of the Internet's most basic problems is the challenge Reddit has set for itself, and the entire Internet has a front-row seat to watch it try.

Huffman’s Hard Road

Huffman's first gambit as CEO was to announce new boundaries. Reddit would create a new category for offensive content (“you know it when you see it,” Huffman said) that would require users to opt in to its forums and would never be monetized via advertising. The site would also use an outright ban on content that harasses, bullies or abuses.

In keeping with a standard established under Pao to “ban behavior, not ideas,” Huffman offered examples of what would stay and what would go. A subreddit that encouraged the physical harm of women would be banned, he said. A subreddit promoting racist views could say. “It’s okay to say, ‘I don’t like this group of people,’” Huffman said during the AMA. “It’s not ok to say, ‘I’m going to kill this group of people.’”

'What does it mean that people get all sorts of value out of their online communities at the same time that a company is trying to make a profit out of them?'

After the AMA, critics decried the new policies as an effort that didn’t truly crack down on harassment. “As far as purges of contentious subreddits go, Huffman’s post suggests that a complete clean-out of Reddit’s underbelly is out of the question for all but the most extreme communities,” Charlie Warzel wrote on Buzzfeed. “This vague line of reasoning is hardly a new one for Reddit’s leadership. And, more critically, it fails to address Reddit’s very real harassment problem.”

Warzel argued that “in spite of numerous public meltdowns, petitions, threats, and executive leadership changes,” Reddit has largely stayed the same.

The Power of Moderation

But the very nature of Reddit means that its problems cannot possibly be solved by changes in policy alone. The hundreds of subreddits taken private during the recent revolt shined a light on the immense power of Reddit’s band of unpaid volunteer moderators, volunteers Reddit needs in order to exist.

For years, some moderators have protested the lack of communication between the company and the community. Among their complaints: a lack of good tools for dealing with harassment in the subreddits they manage. According to journalist Aaron Sankin at The Daily Dot, many of Reddit’s unpaid moderators were unhappy because, while Reddit had updated its policy aimed at curbing harassment, the site itself offered no more effective ways to actually enable anti-harassment efforts by its own volunteers. And these are tools that mods seem to want.

During the AMA, Huffman took every opportunity to say the company’s engineers were working on tools for mods. “We won’t formally change our policy until we have the tools to support it,” he said.

According to Nathan Matias of the MIT Media Lab Center for Civic Media, who has researched Reddit extensively, the moderators are holding the company to its promises, describing how some subreddits have actually put timers onto their pages to make sure the tools the site’s leaders promised would be ready in the timeframes discussed.

But moderators are far more than just monitors who ban the accounts of those who step out of line, Matias says. “They’re promoters and facilitators,” he says of the immense work that goes into fostering a community on Reddit.

“But what does it mean that people get all sorts of value out of their online communities at the same time that a company is trying to make a profit out of them?”

Surfacing the Good

Details on how much pressure Reddit is actually under to make money are scarce. The company recently announced it would launch an original video project and has alluded to an expansion of its nascent advertising business. Though the company, according to its lawyers, is valued internally at $250 million, Reddit reported its 2014 ad revenue to be a modest $8.3 million, a pittance for the tenth most-trafficked website in the US.

But the site’s leaders are presenting a united front in saying it has no motivation to make an immediate profit. During the AMA, Huffman told a user that the push to curb ugly content had nothing to do with making money.

Reached afterward by email, Reddit board member and Y Combinator president Sam Altman told WIRED, “The company has lots and lots of cash and definitely should not try to monetize too aggressively or too soon.”

That cash cushion would seem to give Reddit breathing room as it figures out how to solve its problems, all of which can be distilled into one goal: how to curb the bad while keeping the good.

Some have proposed overhauling the system completely, pointing out that anonymity often breeds hateful speech. But anonymity and pseudonymity also allow targets of harassment to feel more free to express themselves, as the controversy over Facebook's real name policy makes clear. Ultimately, the lesson of Reddit may not be how to fix the Internet's problems but to show the limits of what technology and design can do.

“These problems go deeper–they’re rooted in the wider problems of racism, sexism and hate that we have in our society,” Matias says. “And the idea that we could make systems by design that prevents us from being the society we are when we interact online seems hopelessly utopian.”