Before Ross Ulbricht has even been sentenced for his conviction last month of running the Silk Road's massive online narcotics operation, his defense team has launched a motion to grant him another trial. And their request is based in part on fresh evidence that the federal government surveilled the Silk Road's server in Iceland without a warrant, and may have even launched hacking attacks against the site.

On Friday evening, Ulbricht's attorneys filed a new memo to Judge Katherine Forrest seeking to not only give Ulbricht a new trial, but to re-open an earlier motion to suppress all the evidence in the case that resulted from law enforcement's identification of the Silk Road server. The defense team argues that investigation included illegal searches tantamount to hacking the server without a warrant, which would violate Ulbricht's Fourth Amendment rights. Records of the investigation that were made available to Ulbricht only just before his trial in January, the defense says, show that Department of Homeland Security investigators were actively attempting to break the protections of the anonymity software Tor, which hid the Silk Road's location.

"[This evidence] requires the Court to reopen Mr. Ulbricht's suppression motion and to grant it in its entirety on the basis of this information, or at the very least conduct an evidentiary hearing," the memo reads. "In the context of Mr. Ulbricht's suppression motion, this surveillance raises some novel Fourth Amendment issues, also provides further evidence that the government discovered the [IP] address for the Iceland server...through warrantless Tor network surveillance."

The memo references a text message conversation between DHS special agent Jared Der-Yeghiayan and a confidential informant in which the two discuss running or gaining control of a Tor exit node, one of the thousands of proxy computers in Tor's volunteer network that represent the last "hop" a user's data takes before reaching a destination website. "Are we up yet on the exit node yet?" Der-Yeghiayan wrote to the unidentified informant on August 4th, 2012. "Success!" the informant responds. "100 percent running, logging, and recording."

On another occasion, according to the defense's memo, Der-Yeghiayan and the informant discussed the possibility of using a distributed denial of service attack against the Silk Road. That sort of attack, which floods a target site with fraudulent data requests. Security researchers and Dark Web users have long speculated that denial of service attacks in combination with running malicious exit nodes might reveal the IP address of a "Tor hidden service" like the Silk Road.

The defense admits it doesn't know if law enforcement investigators ever carried out their DDOS attack idea. But its memo points out that the Silk Road is known to have suffered from serious DDOS attacks in the spring of 2013, the same time that the government has previously claimed to have located the Silk Road's Icelandic server through less controversial means.

The question of just how law enforcement identified the Silk Road server was never broached in Ulbricht's trial, but it was a major focus of the case's pre-trial arguments. In response to the defense's initial questions about how the site's hidden server was found, prosecutors first responded that a misconfiguration of the site's CAPTCHA had leaked its IP address when FBI investigators typed some "miscellaneous" characters into entry fields on the site's homepage. But security researchers and Ulbricht's defense immediately began poking holes in that story, arguing that the FBI's actions sounded more like warrantless hacking than a simple observation of identifying data revealed by the site's homepage. In response, the prosecution all but admitted that the site was hacked, arguing that even if the FBI had compromised the site with hacking techniques, that intrusion would have been legal based on the server's foreign location and Ulbricht's unwillingness to declare his ownership of the machine. The judge in the case ultimately agreed, denying the defense's request for an evidentiary hearing about the server investigation.

The possibility of an illegal search is only one of the issues the defense raises in its call for a new trial. It also claims that the prosecution didn't give the defense enough time to review the evidence it provided for the trial. And it protests the judge's decision not to allow the defense to call bitcoin expert Andreas Antonopoulos as a witness. Earlier, Ulbricht's defense team used both of those issues as grounds to call for a mistrial. In all, Ulbricht's lead defense attorney Joshua Dratel called for a mistrial five times over the month-long trial.

With that track record—and given that Ulbricht has already been tried and convicted—it seems highly unlikely that he'll be granted a new trial based on the defense's new memo. But the filing is no doubt a part of the defense's larger strategy to highlight issues in the case that warrant an appeal, which Dratel has already said he plans to file.

Aside from Ulbricht's legal fate, the security community has closely watched the Silk Road case in part due to the mystery of how the feds initially discovered the site's server despite Tor's anonymity protections. That question holds significance not just for Ulbricht, but for the entire Dark Web of Tor hidden services that seek to evade law enforcement. And with the defense's latest hail-mary tactic, there's once again hope that question will be answered.

Here's the full filing from Ulbricht's defense team.

Ulbricht Appeal