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@kidchenko kidchenko commented Feb 4, 2026

πŸ›‘οΈ Sentinel: [CRITICAL] Fix TOCTOU race condition in SSH key setup

🚨 Severity: CRITICAL
πŸ’‘ Vulnerability: Time-of-Check Time-of-Use (TOCTOU) race condition where SSH private key was written with default permissions before being restricted.
🎯 Impact: On a multi-user system, an attacker could potentially read the private key during the brief window between file creation and chmod.
πŸ”§ Fix: Wrapped the file creation in a subshell with umask 077 to ensure atomic 0600 permissions.
βœ… Verification: Verified syntax with bash -n and visual inspection. The umask 077 guarantees the file is created with read/write access for the owner only.


PR created automatically by Jules for task 13455434870920061545 started by @kidchenko

Summary by CodeRabbit

  • Bug Fixes

    • Enhanced SSH private key file permission handling during restoration to improve security.
  • Documentation

    • Added documentation regarding shell script file permission considerations.

Wrapping the private key file creation in a subshell with `umask 077`
ensures the file is created with restricted permissions (0600)
atomically, preventing a window where it might be world-readable.

- tools/setup-ssh-keys.sh: Use umask 077 for private key creation
- .jules/sentinel.md: Record security learning

Co-authored-by: kidchenko <5432753+kidchenko@users.noreply.github.com>
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coderabbitai bot commented Feb 4, 2026

πŸ“ Walkthrough

Walkthrough

A TOCTOU vulnerability in SSH key file handling was documented and fixed. The code change modifies the private key restoration process to use umask 077 within a subshell, ensuring atomic file creation with secure 0600 permissions instead of the prior approach of writing first, then applying chmod separately.

Changes

Cohort / File(s) Summary
Security Documentation
.jules/sentinel.md
New file documenting a TOCTOU vulnerability in SSH key handling, detailing the race condition where private keys could briefly be world-readable, and prescribing mitigation using umask 077.
SSH Key Permission Hardening
tools/setup-ssh-keys.sh
Modified private key restoration process to write the key within a subshell with umask 077, replacing the separate write-then-chmod pattern with atomic secure creation.

Estimated code review effort

🎯 2 (Simple) | ⏱️ ~12 minutes

Poem

🐰 A rabbit hops through keys so bright,
Once written bare to prying sightβ€”
With umask's shield, secure and tight,
No window open for the night,
Our secrets safe, permissions right! πŸ”

πŸš₯ Pre-merge checks | βœ… 3
βœ… Passed checks (3 passed)
Check name Status Explanation
Description Check βœ… Passed Check skipped - CodeRabbit’s high-level summary is enabled.
Title check βœ… Passed The title 'Fix SSH key creation race condition' directly addresses the main security vulnerability being fixed (TOCTOU race condition in SSH key creation) and is specific and clear.
Docstring Coverage βœ… Passed Docstring coverage is 100.00% which is sufficient. The required threshold is 80.00%.

✏️ Tip: You can configure your own custom pre-merge checks in the settings.

✨ Finishing touches
  • πŸ“ Generate docstrings
πŸ§ͺ Generate unit tests (beta)
  • Create PR with unit tests
  • Post copyable unit tests in a comment
  • Commit unit tests in branch sentinel/fix-ssh-key-race-condition-13455434870920061545

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Actionable comments posted: 1

πŸ€– Fix all issues with AI agents
In @.jules/sentinel.md:
- Around line 1-4: Update the markdown to satisfy the linter: change the first
heading from "## 2024-10-24 - Shell Script Race Conditions" to a top-level
heading using "#" and add a blank line after it, then wrap or break long lines
(lines describing Vulnerability, Learning, and Prevention) so they are <=80
characters; keep the same content but reflow text or split into multiple short
lines and ensure the code reference `tools/setup-ssh-keys.sh` and the
recommendation `umask 077`/`chmod` remain intact.

Comment on lines +1 to +4
## 2024-10-24 - Shell Script Race Conditions
**Vulnerability:** Found a Time-of-Check Time-of-Use (TOCTOU) race condition in `tools/setup-ssh-keys.sh` where a private key was written to disk with default permissions before being restricted with `chmod`.
**Learning:** Shell scripts often default to permissive `umask` (e.g., 022), making files world-readable for a brief window during creation.
**Prevention:** Always use `umask 077` in a subshell before writing sensitive files to ensure they are created with restricted permissions (0600) atomically.
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⚠️ Potential issue | 🟑 Minor

Fix markdown linting failures flagged by CI.

The documentation content is accurate, but the linter reports several issues:

  • MD041: First line should be a top-level heading (# not ##)
  • MD022: Heading needs a blank line after it
  • MD013: Lines 2-4 exceed 80 characters
πŸ“ Proposed fix to address linting issues
-## 2024-10-24 - Shell Script Race Conditions
-**Vulnerability:** Found a Time-of-Check Time-of-Use (TOCTOU) race condition in `tools/setup-ssh-keys.sh` where a private key was written to disk with default permissions before being restricted with `chmod`.
-**Learning:** Shell scripts often default to permissive `umask` (e.g., 022), making files world-readable for a brief window during creation.
-**Prevention:** Always use `umask 077` in a subshell before writing sensitive files to ensure they are created with restricted permissions (0600) atomically.
+# Sentinel Security Learnings
+
+## 2024-10-24 - Shell Script Race Conditions
+
+**Vulnerability:** Found a Time-of-Check Time-of-Use (TOCTOU) race condition
+in `tools/setup-ssh-keys.sh` where a private key was written to disk with
+default permissions before being restricted with `chmod`.
+
+**Learning:** Shell scripts often default to permissive `umask` (e.g., 022),
+making files world-readable for a brief window during creation.
+
+**Prevention:** Always use `umask 077` in a subshell before writing sensitive
+files to ensure they are created with restricted permissions (0600) atomically.
πŸ“ Committable suggestion

‼️ IMPORTANT
Carefully review the code before committing. Ensure that it accurately replaces the highlighted code, contains no missing lines, and has no issues with indentation. Thoroughly test & benchmark the code to ensure it meets the requirements.

Suggested change
## 2024-10-24 - Shell Script Race Conditions
**Vulnerability:** Found a Time-of-Check Time-of-Use (TOCTOU) race condition in `tools/setup-ssh-keys.sh` where a private key was written to disk with default permissions before being restricted with `chmod`.
**Learning:** Shell scripts often default to permissive `umask` (e.g., 022), making files world-readable for a brief window during creation.
**Prevention:** Always use `umask 077` in a subshell before writing sensitive files to ensure they are created with restricted permissions (0600) atomically.
# Sentinel Security Learnings
## 2024-10-24 - Shell Script Race Conditions
**Vulnerability:** Found a Time-of-Check Time-of-Use (TOCTOU) race condition
in `tools/setup-ssh-keys.sh` where a private key was written to disk with
default permissions before being restricted with `chmod`.
**Learning:** Shell scripts often default to permissive `umask` (e.g., 022),
making files world-readable for a brief window during creation.
**Prevention:** Always use `umask 077` in a subshell before writing sensitive
files to ensure they are created with restricted permissions (0600) atomically.
🧰 Tools
πŸͺ› GitHub Check: Lint Documentation

[failure] 4-4: Line length
.jules/sentinel.md:4:81 MD013/line-length Line length [Expected: 80; Actual: 157] https://github.com/DavidAnson/markdownlint/blob/v0.34.0/doc/md013.md


[failure] 3-3: Line length
.jules/sentinel.md:3:81 MD013/line-length Line length [Expected: 80; Actual: 140] https://github.com/DavidAnson/markdownlint/blob/v0.34.0/doc/md013.md


[failure] 2-2: Line length
.jules/sentinel.md:2:81 MD013/line-length Line length [Expected: 80; Actual: 208] https://github.com/DavidAnson/markdownlint/blob/v0.34.0/doc/md013.md


[failure] 1-1: First line in a file should be a top-level heading
.jules/sentinel.md:1 MD041/first-line-heading/first-line-h1 First line in a file should be a top-level heading [Context: "## 2024-10-24 - Shell Script R..."] https://github.com/DavidAnson/markdownlint/blob/v0.34.0/doc/md041.md


[failure] 1-1: Headings should be surrounded by blank lines
.jules/sentinel.md:1 MD022/blanks-around-headings Headings should be surrounded by blank lines [Expected: 1; Actual: 0; Below] [Context: "## 2024-10-24 - Shell Script Race Conditions"] https://github.com/DavidAnson/markdownlint/blob/v0.34.0/doc/md022.md

πŸ€– Prompt for AI Agents
In @.jules/sentinel.md around lines 1 - 4, Update the markdown to satisfy the
linter: change the first heading from "## 2024-10-24 - Shell Script Race
Conditions" to a top-level heading using "#" and add a blank line after it, then
wrap or break long lines (lines describing Vulnerability, Learning, and
Prevention) so they are <=80 characters; keep the same content but reflow text
or split into multiple short lines and ensure the code reference
`tools/setup-ssh-keys.sh` and the recommendation `umask 077`/`chmod` remain
intact.

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