Skip to content

πŸ›‘οΈ Sentinel: [HIGH] Fix TOCTOU vulnerability in SSH key creation#24

Open
kidchenko wants to merge 1 commit intomainfrom
sentinel-fix-ssh-toctou-11977943561005832187
Open

πŸ›‘οΈ Sentinel: [HIGH] Fix TOCTOU vulnerability in SSH key creation#24
kidchenko wants to merge 1 commit intomainfrom
sentinel-fix-ssh-toctou-11977943561005832187

Conversation

@kidchenko
Copy link
Owner

@kidchenko kidchenko commented Feb 8, 2026

πŸ›‘οΈ Sentinel: [HIGH] Fix TOCTOU vulnerability in SSH key creation

🚨 Severity: HIGH
πŸ’‘ Vulnerability: The SSH private key was being created with default permissions (potentially world-readable) before chmod 600 was applied. This created a Time-of-Check Time-of-Use (TOCTOU) race condition where the key could be read by other users on the system during the window between creation and permission modification.
🎯 Impact: An attacker with local access could potentially read the private key during the race condition window, compromising the user's SSH access.
πŸ”§ Fix:

  1. Used (umask 077; command > file) pattern to ensure the file is created with restricted permissions (-rw-------) atomically.
  2. Updated directory creation to use mkdir -p -m 700 and enforced chmod 700 even if the directory already exists.
    βœ… Verification:
  • Verified the issue with a reproduction script showing default file creation respects umask (often 022).
  • Verified the fix ensures files are created with 600 permissions immediately.
  • Validated script syntax with bash -n.

PR created automatically by Jules for task 11977943561005832187 started by @kidchenko

Summary by CodeRabbit

  • Bug Fixes
    • Enhanced SSH key creation to enforce appropriately restrictive permissions for both private key files and their containing directories.
    • Improved the SSH key restoration process with stricter permission controls during sensitive file creation and handling to better protect key material.

- Use `umask 077` in a subshell when writing SSH private keys to disk.
- Ensure SSH directory has 700 permissions on creation and if it already exists.
- Add security journal entry in `.jules/sentinel.md`.

This prevents a brief window where the private key file could be world-readable before `chmod 600` is applied.

Co-authored-by: kidchenko <5432753+kidchenko@users.noreply.github.com>
@google-labs-jules
Copy link
Contributor

πŸ‘‹ Jules, reporting for duty! I'm here to lend a hand with this pull request.

When you start a review, I'll add a πŸ‘€ emoji to each comment to let you know I've read it. I'll focus on feedback directed at me and will do my best to stay out of conversations between you and other bots or reviewers to keep the noise down.

I'll push a commit with your requested changes shortly after. Please note there might be a delay between these steps, but rest assured I'm on the job!

For more direct control, you can switch me to Reactive Mode. When this mode is on, I will only act on comments where you specifically mention me with @jules. You can find this option in the Pull Request section of your global Jules UI settings. You can always switch back!

New to Jules? Learn more at jules.google/docs.


For security, I will only act on instructions from the user who triggered this task.

@coderabbitai
Copy link

coderabbitai bot commented Feb 8, 2026

πŸ“ Walkthrough

Walkthrough

Documentation and code updates address SSH key file permission vulnerabilities. A sentinel entry documents a TOCTOU race condition in SSH private key creation with default permissions before chmod. The setup script now conditionally creates SSH directories with secure mode 700 and retrieves private keys within a restricted umask 077 environment.

Changes

Cohort / File(s) Summary
SSH Key Permission Security
tools/setup-ssh-keys.sh
SSH directory creation now conditional with secure mode 700; private key retrieval wrapped with strict umask 077 to ensure restricted permissions during file creation.
Vulnerability Documentation
.jules/sentinel.md
Added documentation of TOCTOU race condition in SSH key creation, with learning notes on shell redirection behavior with umask and prevention examples using subshell with umask 077.

Estimated code review effort

🎯 2 (Simple) | ⏱️ ~12 minutes

Poem

🐰 Hop, hop, hooray! The keys are now safe,
With umask 077, no permissions to chafe,
The directories whisper their secrets with care,
No races or vulnerabilities hiding in there! 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 directly addresses the main changeβ€”fixing a TOCTOU vulnerability in SSH key creationβ€”which aligns with the primary objective and changes across both modified files.
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-toctou-11977943561005832187

Thanks for using CodeRabbit! It's free for OSS, and your support helps us grow. If you like it, consider giving us a shout-out.

❀️ Share

Comment @coderabbitai help to get the list of available commands and usage tips.

Copy link

@coderabbitai coderabbitai bot left a comment

Choose a reason for hiding this comment

The reason will be displayed to describe this comment to others. Learn more.

Actionable comments posted: 2

πŸ€– Fix all issues with AI agents
In @.jules/sentinel.md:
- Around line 2-4: The three long Markdown lines ("Vulnerability:", "Learning:",
"Prevention:") exceed the 80-character limit; reflow each paragraph to lines ≀80
chars by inserting line breaks at natural sentence or clause boundaries (e.g.,
after "race condition", after "umask", and before the example), keeping the
original headings and content intact and preserving the example command `(umask
077; command > file)` on its own wrapped line so the file complies with MD013.
- Line 1: Update the sentinel markdown: fix the date in the existing heading
from "2025-02-08" to "2026-02-08", add a top-level heading "# Sentinel" as the
first line to satisfy MD041, and insert a blank line between that top-level
heading and the "## 2026-02-08 - TOCTOU Race Condition in File Creation" entry
to satisfy MD022; ensure the second-level heading text is updated accordingly to
match the corrected date.
🧹 Nitpick comments (1)
tools/setup-ssh-keys.sh (1)

164-166: Public key file also created with default umask before chmod.

The public key isn't secret so this is low-risk, but for consistency with the private key hardening, you could wrap the public key write in a similar subshell pattern β€” e.g., (umask 133; op read ... > "$PUBLIC_KEY_FILE") to get 0644 immediately.

@@ -0,0 +1,4 @@
## 2025-02-08 - TOCTOU Race Condition in File Creation
Copy link

Choose a reason for hiding this comment

The reason will be displayed to describe this comment to others. Learn more.

⚠️ Potential issue | 🟑 Minor

Date typo: should be 2026, not 2025.

The PR was created on 2026-02-08, but the heading says 2025-02-08.

Also, the markdown linter flags MD041 (first line should be a top-level # heading) and MD022 (blank line required after headings). Consider adding a top-level # Sentinel heading and a blank line before the ## entry.

Proposed fix
-## 2025-02-08 - TOCTOU Race Condition in File Creation
+# Sentinel
+
+## 2026-02-08 - TOCTOU Race Condition in File Creation
+
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
## 2025-02-08 - TOCTOU Race Condition in File Creation
# Sentinel
## 2026-02-08 - TOCTOU Race Condition in File Creation
🧰 Tools
πŸͺ› GitHub Check: Lint Documentation

[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: "## 2025-02-08 - TOCTOU Race Co..."] 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: "## 2025-02-08 - TOCTOU Race Condition in File Creation"] https://github.com/DavidAnson/markdownlint/blob/v0.34.0/doc/md022.md

πŸ€– Prompt for AI Agents
In @.jules/sentinel.md at line 1, Update the sentinel markdown: fix the date in
the existing heading from "2025-02-08" to "2026-02-08", add a top-level heading
"# Sentinel" as the first line to satisfy MD041, and insert a blank line between
that top-level heading and the "## 2026-02-08 - TOCTOU Race Condition in File
Creation" entry to satisfy MD022; ensure the second-level heading text is
updated accordingly to match the corrected date.

Comment on lines +2 to +4
**Vulnerability:** The SSH private key was being created with default permissions (potentially world-readable) before `chmod 600` was applied. This created a race condition where the key could be read by other users on the system.
**Learning:** Shell redirection (`>`) creates files with the current `umask` before any subsequent `chmod` command is executed.
**Prevention:** Use `umask 077` in a subshell when creating sensitive files to ensure they are created with restricted permissions from the start. Example: `(umask 077; command > file)`.
Copy link

Choose a reason for hiding this comment

The reason will be displayed to describe this comment to others. Learn more.

⚠️ Potential issue | 🟑 Minor

Markdown lint: line length exceeds 80 characters (MD013).

Lines 2–4 all exceed the 80-character limit flagged by the linter. Wrap the long lines to comply.

🧰 Tools
πŸͺ› GitHub Check: Lint Documentation

[failure] 4-4: Line length
.jules/sentinel.md:4:81 MD013/line-length Line length [Expected: 80; Actual: 186] 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: 127] 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: 230] https://github.com/DavidAnson/markdownlint/blob/v0.34.0/doc/md013.md

πŸ€– Prompt for AI Agents
In @.jules/sentinel.md around lines 2 - 4, The three long Markdown lines
("Vulnerability:", "Learning:", "Prevention:") exceed the 80-character limit;
reflow each paragraph to lines ≀80 chars by inserting line breaks at natural
sentence or clause boundaries (e.g., after "race condition", after "umask", and
before the example), keeping the original headings and content intact and
preserving the example command `(umask 077; command > file)` on its own wrapped
line so the file complies with MD013.

Sign up for free to join this conversation on GitHub. Already have an account? Sign in to comment

Labels

None yet

Projects

None yet

Development

Successfully merging this pull request may close these issues.

1 participant