Coding Agent Horror Stories: The rm -rf ~/ Incident | Docker

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This is Part 2 of our AI Coding Agent Horror Stories series, an in-depth look at real-world security incidents exposing the vulnerabilities in AI coding agents, and how Docker Sandboxes deliver workspace-scoped isolation that contains the worst failures at the execution layer.
In part 1 of this series, we mapped six categories of AI coding agent failures and the architectural reason they keep happening: the agent runs as you, on your filesystem, with your credentials, and nothing sits between the model’s decision and the shell’s execution. For Part 2, we’re going deep on the most destructive failure mode in the entire ecosystem: an AI coding agent deleting a developer’s entire home directory in a single command.
In December 2025, a Reddit user posting under the handle u/LovesWorkin shared what became one of the most-discussed AI coding agent incidents of the year. They had asked Claude Code to clean up an old repository. Claude executed rm -rf tests/ patches/ plan/ ~/, and the trailing ~/ wiped their entire Mac.
This wasn’t a CVE. It wasn’t a sophisticated attack. It was the AI coding agent doing exactly what it was told, in a way the user did not anticipate, with no architectural boundary to catch the mistake.
In this issue, you’ll learn:
Each “Horror Story” in this series examines a real-world incident that turns laboratory findings into production disasters. These aren’t hypothetical attacks. They’re documented cases with named victims, screenshotted command logs, and in several cases, public apologies from the vendors. Our goal is to show the human impact behind the security statistics, demonstrate how these failures unfold in practice, and provide concrete guidance on protecting your AI development infrastructure through Docker’s workspace-scoped execution model.
The story begins with something every developer has done: asking the agent to clean up an old repository.
On December 8, 2025,a developer posting under the handle u/LovesWorkin shared a Reddit thread on r/ClaudeAI with the title that says everything: “Claude CLI deleted my entire home directory! Wiped my whole mac.” The post climbed past 1,500 upvotes within hours, was amplified by Simon Willison on X, covered by Gigazine in Japan on December 16, and became one of the most-discussed AI coding agent incidents of 2025.
The setup was unremarkable. The user asked Claude Code to clean up packages in an old repository. Routine maintenance, the kind any developer would hand off without thinking. Claude generated and executed:
On the surface, this is a command to delete three project directories. The fatal error is the trailing ~/. In Unix, ~ expands to the user’s home directory. ~/ with the trailing slash means “everything inside the home directory.” Combined with rm -rf, which removes recursively and without confirmation, the command deletes the user’s entire home directory in a single shot.
Within seconds, the developer had lost:
There was no recovery. As the developer put it in the original thread: “It nuked my whole Mac! What the hell?”
Caption: Once an AI agent gains direct filesystem access, “organize my desktop” can become catastrophic.
This wasn’t a one-off. It was an instance of a pattern.
On October 21, 2025, weeks before the LovesWorkin incident, developer Mike Wolak filed GitHub issue #10077 against the Claude Code repository. Wolak’s report described a similar failure on Ubuntu/WSL2: Claude Code had executed rm -rf starting from root, and the logs showed thousands of “Permission denied” messages for /bin, /boot, and /etc as the agent worked its way through the system trying to delete files it didn’t own. Every user-owned file on the system was gone. Anthropic tagged the issue area:security and bug. The damning detail in Wolak’s report: he was not running with --dangerously-skip-permissions. Claude Code’s permission system simply failed to detect that the agent’s command would expand destructively before the user approved it.
Two weeks later, on November 28, 2025, GitHub issue #12637 documented yet another variant. Claude Code had earlier created a directory literally named ~ by mistake. Later, when the agent tried to clean up that directory by running an unquoted rm -rf ~, the shell expanded ~ to the user’s actual home directory before rm saw the argument. Same destructive outcome, completely different mechanism. The agent had found a new way to destroy a developer’s work.
Shortly after the January 2026 launch of Anthropic’s Claude Cowork, Nick Davidov, founder of a venture capital firm, used Anthropic’s Claude Cowork, a general-purpose AI agent product to organize his wife’s desktop. He explicitly granted permission for temporary Office files only. The agent deleted a folder containing 15 years of family photos, somewhere between 15,000 and 27,000 files, via terminal commands that bypassed the macOS Trash entirely. Davidov recovered the photos only because iCloud’s 30-day retention happened to still be in effect. The Trash had been bypassed entirely.
These aren’t isolated stories. They’re the same story with different file paths.
To understand why these incidents keep happening, we need to look at the architecture of how a modern AI coding agent executes commands on a developer’s machine. The agent is doing exactly what its design says it should do. The architecture is the failure.
That last point is the one that matters. The flag exists because the default behavior, asking for confirmation on every shell command, makes multi-step tasks tedious. Developers add the flag to make the agent useful. The agent then becomes capable of executing destructive commands without intervention. The flag is named honestly. It is a dangerous flag. But it is also a popular one, because the alternative is approving every ls and cat the agent runs.
The vulnerability happens between steps 2 and 3. The agent reasons about what command to run. The sh