When news website 100Reporters launched this past October, it had everything you’d expect from a promising journalistic startup: top journalists, funding, partnerships with established news organizations. But 100Reporters also came equipped with Whistleblower Alley, its own WikiLeaks-style leaking portal.

Started by Diana Jean Schemo and Philip Shenon, both former New York Times journalists, 100Reporters covers corruption in the US and abroad. It’s a beat that often relies on risk-taking sources who’ve been promised anonymity from journalists. But as digital communications become easier to monitor, confidentiality becomes harder to ensure. “They don’t tolerate a free press in Afghanistan, Somalia, or Burma, but we want to let these people get information out and tell their story,” says Schemo. “We built Whistleblower Alley as a place to have secure, encrypted communications without any sort of compromise in the transmission itself.”

100Reporters isn’t the first news organization to offer a secure communications portal for sources. In the past year, many variations of this concept have emerged, and just like the inspiration for it all, WikiLeaks, the short history of these ventures hasn’t been so smooth.

In January 2011, mere weeks after the arrest of Julian Assange, Al Jazeera’s Transparency Unit (AJTU) was unveiled, the first big-media attempt at a whistleblower platform. Shortly afterwards, then-New York Times editor Bill Keller spoke of a similar Times initiative, calling it an “EZ Pass Lane for Leakers,” but it’s nowhere to be seen as of yet. (Andy Greenberg was told in October that it was “still in the early stages.”) The Wall Street Journal’s SafeHouse followed in May, but a month after its debut, the Electronic Frontier Foundation, a digital rights advocacy group, published a piece titled “WSJ and Al-Jazeera Lure Whistleblowers with False Promises of Anonymity.” The piece included a subhead which read, “They Reserve the Right to Sell You Out” breaking down both the WSJ’s and Al Jazeera’s terms of service; each included a caveat that they could reveal the source of a submission if asked by law enforcement or other third parties.

Al Jazeera later amended some of the problems for which they were criticized, encouraging people to be proactive about protecting their own anonymity, and being more specific about the circumstances under which they would disclose information. The Wall Street Journal told Forbes’s Andy Greenberg their terms of service was set up that way “to provide flexibility to react to extraordinary circumstances.” The Wall Street Journal declined a CJR request to speak about Safehouse; The New York Times and Al Jazeera never responded when asked for an interview.

The strongest way for sites like these to protect their sources is to build the site in a way that even the creator can’t trace what is received, a standard many leaks sites adhere to. Danny O’Brien, a technology journalist and the Internet advocacy coordinator for the Committee to Protect Journalists, says this blanket anonymity is less workable at a news organization, where anonymous sources can prove difficult to use. “There’s a difference between meeting up with Deep Throat and knowing who he is,” says O’Brien, “and simply meeting with someone who insists they are called deep throat and won’t tell you anything else about them.” Most of the legal safeguards journalists have are based on them knowing the source’s identity but being protected from having to reveal that. Trust in the subsequent story is drawn from the assumption that the anonymous source has been vetted, and there’s reason to believe what they’re saying.

O’Brien refers to this discrepancy as a “culture clash” between news organizations and the hacker subculture. Leak platforms that come from the latter are often constructed in a way that’s “far less easy to use in order to insure against even very uncommon attacks,” says O’Brien, while news organizations have taken a “good-enough approach.”

WikiLeaks’s guarantee of anonymity is such that even they don’t know who’s leaking to them, because, as Assange put it to Frontline in May, “the best way to keep a secret is to never have it.” But it’s now been over 400 days since Assange’s house arrest and the financial embargo on WikiLeaks’s donations, not exactly the most inviting circumstances for developing a whistleblower platform. “Large media organizations have a lot to lose,” says O’Brien, “and they don’t appear prepared to lose it.” WikiLeaks’s homepage says their hardships have forced them to devote all their energy to fundraising. This December, they published for the first time in eight months with the “Spy Files,” an inside look at the booming surveillance industry and its government customers (more on that here). Following that release, Assange said he would be revamping WikiLeaks’s submission system to deal with outdated security features on the site.

Alysia Santo is a former assistant editor at CJR.