It turns out that installing spyware on smartphones isn’t as easy as it sounds.

Lawyers for Sam Bankman-Fried said that they have encountered unexpected challenges while attempting to comply with specific bail conditions set forth by the court. The issue in question is installing software on his parents’ smartphones that would take pictures of the user every five minutes in order to constantly monitor who was using them.

“We learned recently that the monitoring software installed on the new cellphones we purchased for Mr. Bankman-Fried’s parents cannot, in fact, automatically photograph the device’s user every five minutes as required by the order,” wrote attorneys Mark Cohen and Christian Everdell.

While the model of mobile phones being used was not disclosed, modern smartphones—including iPhones running iOS, Google Android, and devices running privacy-focused operating systems like GrapheneOS—have stepped up their security measures, including app sandboxing.

Sandboxing in mobile phones is a security practice that isolates applications in a restricted environment, protecting the device’s operating system and other data from potential harm. It creates a “safe zone” for apps, limiting the impact of malicious software or vulnerabilities.

Also, in October, Apple rolled out a new lockdown mode for iOS 16, iPadOS 16, and macOS Ventura. The optional security feature is designed for those facing advanced digital threats, and limits device functionality—including web browsing restrictions and blocking inbound FaceTime calls—in order to reduce spyware exposure.

“If they wanted to do this, they could either force the use of an [Android-based] device and employ a rootkit to install a custom app, or develop an application that complies with Apple’s App Store terms and conditions,” Steven Walbroehl, co-founder and CTO at blockchain cybersecurity firm Halborn, told Decrypt. “Alternatively, they can jailbreak the device and bypass the operating system’s restrictions.”.

While not illegal, jailbreaking violates Apple’s terms of service and invalidates any warranties.


The defense said it is exploring “alternative solutions” that would monitor Bankman-Fried’s parents’ cell phones as called for in the stipulations of the order.

“It’s not illegal to jailbreak a phone,” Walbroehl said. “The Digital Copyright Act of 2010 grants users the right to root access their phones, but they are legally responsible for abiding by copyright law on what they put it on it.”

In the letter to presiding Judge Lewis Kaplan, SBF’s legal team has requested an extension until Friday, April 21, 2023, to comply with his orders.  The request for an extension is the third one filed by the defense since the initial order on March 28, 2023; previous extensions were granted on April 4 and April 11.

Judge Kaplan approved the request, and until a working solution can be found, Bankman-Fried’s attorneys have asked that his parents be allowed to continue using their existing cell phones.

“We are optimistic that we have found a solution but need until the end of this week to conduct further tests on the monitoring software to confirm its capabilities," the attorneys reported.

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