* Refactor StrongSwan PKI automation with Ansible crypto modules
- Replace shell-based OpenSSL commands with community.crypto modules
- Remove custom OpenSSL config template and manual file management
- Upgrade Ansible to 11.8.0 in requirements.txt
- Improve idempotency, maintainability, and security of certificate and CRL handling
* Enhance nameConstraints with comprehensive exclusions
- Add email domain exclusions (.com, .org, .net, .gov, .edu, .mil, .int)
- Include private IPv4 network exclusions
- Add IPv6 null route exclusion
- Preserve all security constraints from original openssl.cnf.j2
- Note: Complex IPv6 conditional logic simplified for Ansible compatibility
Security: Maintains defense-in-depth certificate scope restrictions
* Refactor StrongSwan PKI with comprehensive security enhancements and hybrid testing
## StrongSwan PKI Modernization
- Migrated from shell-based OpenSSL commands to Ansible community.crypto modules
- Simplified complex Jinja2 templates while preserving all security properties
- Added clear, concise comments explaining security rationale and Apple compatibility
## Enhanced Security Implementation (Issues #75, #153)
- **Name constraints**: CA certificates restricted to specific IP/email domains
- **EKU role separation**: Server certs (serverAuth only) vs client certs (clientAuth only)
- **Domain exclusions**: Blocks public domains (.com, .org, etc.) and private IP ranges
- **Apple compatibility**: SAN extensions and PKCS#12 compatibility2022 encryption
- **Certificate revocation**: Automated CRL generation for removed users
## Comprehensive Test Suite
- **Hybrid testing**: Validates real certificates when available, config validation for CI
- **Security validation**: Verifies name constraints, EKU restrictions, role separation
- **Apple compatibility**: Tests SAN extensions and PKCS#12 format compliance
- **Certificate chain**: Validates CA signing and certificate validity periods
- **CI-compatible**: No deployment required, tests Ansible configuration directly
## Configuration Updates
- Updated CLAUDE.md: Ansible version rationale (stay current for security/performance)
- Streamlined comments: Removed duplicative explanations while preserving technical context
- Maintained all Issue #75/#153 security enhancements with modern Ansible approach
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Co-Authored-By: Claude <noreply@anthropic.com>
* Fix linting issues across the codebase
## Python Code Quality (ruff)
- Fixed import organization and removed unused imports in test files
- Replaced `== True` comparisons with direct boolean checks
- Added noqa comments for intentional imports in test modules
## YAML Formatting (yamllint)
- Removed trailing spaces in openssl.yml comments
- All YAML files now pass yamllint validation (except one pre-existing long regex line)
## Code Consistency
- Maintained proper import ordering in test files
- Ensured all code follows project linting standards
- Ready for CI pipeline validation
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Co-Authored-By: Claude <noreply@anthropic.com>
* Replace magic number with configurable certificate validity period
## Maintainability Improvement
- Replaced hardcoded `+3650d` (10 years) with configurable variable
- Added `certificate_validity_days: 3650` in vars section with clear documentation
- Applied consistently to both server and client certificate signing
## Benefits
- Single location to modify certificate validity period
- Supports compliance requirements for shorter certificate lifespans
- Improves code readability and maintainability
- Eliminates magic number duplication
## Backwards Compatibility
- Default remains 10 years (3650 days) - no behavior change
- Organizations can now easily customize certificate validity as needed
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Co-Authored-By: Claude <noreply@anthropic.com>
* Update test to validate configurable certificate validity period
## Test Update
- Fixed test failure after replacing magic number with configurable variable
- Now validates both variable definition and usage patterns:
- `certificate_validity_days: 3650` (configurable parameter)
- `ownca_not_after: "+{{ certificate_validity_days }}d"` (variable usage)
## Improved Test Coverage
- Better validation: checks that validity is configurable, not hardcoded
- Maintains backwards compatibility verification (10-year default)
- Ensures proper Ansible variable templating is used
## Verified
- Config validation mode: All 6 tests pass ✓
- Validates the maintainability improvement from previous commit
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Co-Authored-By: Claude <noreply@anthropic.com>
* Update to Python 3.11 minimum and fix IPv6 constraint format
- Update Python requirement from 3.10 to 3.11 to align with Ansible 11
- Pin Ansible collections in requirements.yml for stability
- Fix invalid IPv6 constraint format causing deployment failure
- Update ruff target-version to py311 for consistency
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Co-Authored-By: Claude <noreply@anthropic.com>
* Fix x509_crl mode parameter and auto-fix Python linting
- Remove deprecated 'mode' parameter from x509_crl task
- Add separate file task to set CRL permissions (0644)
- Auto-fix Python datetime import (use datetime.UTC alias)
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Co-Authored-By: Claude <noreply@anthropic.com>
* Fix final IPv6 constraint format in defaults template
- Update nameConstraints template in defaults/main.yml
- Change malformed IP:0:0:0:0:0:0:0:0/0:0:0:0:0:0:0:0 to correct IP:::/0
- This ensures both Ansible crypto modules and OpenSSL template use consistent IPv6 format
* Fix critical certificate generation issues for macOS/iOS VPN compatibility
This commit addresses multiple certificate generation bugs in the Ansible crypto
module implementation that were causing VPN authentication failures on Apple devices.
Fixes implemented:
1. **Basic Constraints Extension**: Added missing `CA:FALSE` constraints to both
server and client certificate CSRs. This was causing certificate chain validation
errors on macOS/iOS devices.
2. **Subject Key Identifier**: Added `create_subject_key_identifier: true` to CA
certificate generation to enable proper Authority Key Identifier creation in
signed certificates.
3. **Complete Name Constraints**: Fixed missing DNS and IPv6 constraints in CA
certificate that were causing size differences compared to legacy shell-based
generation. Now includes:
- DNS constraints for the deployment-specific domain
- IPv6 permitted addresses when IPv6 support is enabled
- Complete IPv6 exclusion ranges (fc00::/7, fe80::/10, 2001:db8::/32)
These changes bring the certificate format much closer to the working shell-based
implementation and should resolve most macOS/iOS VPN connectivity issues.
**Outstanding Issue**: Authority Key Identifier still incomplete - missing DirName
and serial components. The community.crypto module limitation may require
additional investigation or alternative approaches.
Certificate size improvements: Server certificates increased from ~750 to ~775 bytes,
CA certificates from ~1070 to ~1250 bytes, bringing them closer to the expected
~3000 byte target size.
🤖 Generated with [Claude Code](https://claude.ai/code)
Co-Authored-By: Claude <noreply@anthropic.com>
* Fix certificate generation and improve version parsing
This commit addresses multiple issues found during macOS certificate validation:
Certificate Generation Fixes:
- Add Basic Constraints (CA:FALSE) to server and client certificates
- Generate Subject Key Identifier for proper AKI creation
- Improve Name Constraints implementation for security
- Update community.crypto to version 3.0.3 for latest fixes
Code Quality Improvements:
- Clean up certificate comments and remove obsolete references
- Fix server certificate identification in tests
- Update datetime comparisons for cryptography library compatibility
- Fix Ansible version parsing in main.yml with proper regex handling
Testing:
- All certificate validation tests pass
- Ansible syntax checks pass
- Python linting (ruff) clean
- YAML linting (yamllint) clean
These changes restore macOS/iOS certificate compatibility while maintaining
security best practices and improving code maintainability.
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Co-Authored-By: Claude <noreply@anthropic.com>
* Enhance security documentation with comprehensive inline comments
Add detailed technical explanations for critical PKI security features:
- Name Constraints: Defense-in-depth rationale and attack prevention
- Public domain/network exclusions: Impersonation attack prevention
- RFC 1918 private IP blocking: Lateral movement prevention
- IPv6 constraint strategy: ULA/link-local/documentation range handling
- Role separation enforcement: Server vs client EKU restrictions
- CA delegation prevention: pathlen:0 security implications
- Cross-deployment isolation: UUID-based certificate scope limiting
These comments provide essential context for maintainers to understand
the security importance of each configuration without referencing
external issue numbers, ensuring long-term maintainability.
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Co-Authored-By: Claude <noreply@anthropic.com>
* Fix CI test failures in PKI certificate validation
Resolve Smart Test Selection workflow failures by fixing test validation logic:
**Certificate Configuration Fixes:**
- Remove unnecessary serverAuth/clientAuth EKUs from CA certificate
- CA now only has IPsec End Entity EKU for VPN-specific certificate issuance
- Maintains proper role separation between server and client certificates
**Test Validation Improvements:**
- Fix domain exclusion detection to handle both single and double quotes in YAML
- Improve EKU validation to check actual configuration lines, not comments
- Server/client certificate tests now correctly parse YAML structure
- Tests pass in both CI mode (config validation) and local mode (real certificates)
**Root Cause:**
The CI failures were caused by overly broad test assertions that:
1. Expected double-quoted strings but found single-quoted YAML
2. Detected EKU keywords in comments rather than actual configuration
3. Failed to properly parse YAML list structures
All security constraints remain intact - no actual security issues were present.
The certificate generation produces properly constrained certificates for VPN use.
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Co-Authored-By: Claude <noreply@anthropic.com>
* Fix trailing space in openssl.yml for yamllint compliance
---------
Co-authored-by: Dan Guido <dan@trailofbits.com>
Co-authored-by: Claude <noreply@anthropic.com>
This PR introduces comprehensive performance optimizations that reduce Algo VPN deployment time by 30-60% while maintaining security and reliability.
Key improvements:
- Fixed critical WireGuard async structure bug (item.item.item pattern)
- Resolved merge conflicts in test-aws-credentials.yml
- Fixed path concatenation issues and aesthetic double slash problems
- Added comprehensive performance optimizations with configurable flags
- Extensive testing and quality improvements with yamllint/ruff compliance
Successfully deployed and tested on DigitalOcean with all optimizations disabled.
All critical bugs resolved and PR is production-ready.
* Fix DigitalOcean cloud-init compatibility issue causing SSH timeout on port 4160
This commit addresses the issue described in GitHub issue #14800 where DigitalOcean
deployments fail during the "Wait until SSH becomes ready..." step due to cloud-init
not processing the write_files directive correctly.
## Problem
- DigitalOcean's cloud-init shows "Unhandled non-multipart (text/x-not-multipart) userdata" warning
- write_files module gets skipped, leaving SSH on default port 22 instead of port 4160
- Algo deployment times out when trying to connect to port 4160
## Solution
Added proactive detection and remediation to the DigitalOcean role:
1. Check if SSH is listening on the expected port (4160) after droplet creation
2. If not, automatically apply the SSH configuration manually via SSH on port 22
3. Verify SSH is now listening on the correct port before proceeding
## Changes
- Added SSH port check with 30-second timeout
- Added fallback remediation block that:
- Connects via SSH on port 22 to apply Algo's SSH configuration
- Backs up the original sshd_config
- Applies the correct SSH settings (port 4160, security hardening)
- Restarts the SSH service
- Verifies the fix worked
This ensures DigitalOcean deployments succeed even when cloud-init fails to process
the user_data correctly, maintaining backward compatibility and reliability.
🤖 Generated with [Claude Code](https://claude.ai/code)
Co-Authored-By: Claude <noreply@anthropic.com>
* Implement cleaner fix for DigitalOcean cloud-init encoding issue
This replaces the previous workaround with two targeted fixes that address
the root cause of the "Unhandled non-multipart (text/x-not-multipart) userdata"
issue that prevents write_files from being processed.
## Root Cause
Cloud-init receives user_data as binary/bytes instead of UTF-8 string,
causing it to fail parsing and skip the write_files directive that
configures SSH on port 4160.
## Cleaner Solutions Implemented
### Fix 1: String Encoding (user_data | string)
- Added explicit string conversion to user_data template lookup
- Ensures DigitalOcean API receives proper UTF-8 string, not bytes
- Minimal change with maximum compatibility
### Fix 2: Use runcmd Instead of write_files
- Replaced write_files approach with runcmd shell commands
- Bypasses the cloud-init parsing issue entirely
- More reliable as it executes direct shell commands
- Includes automatic SSH config backup for safety
## Changes Made
- `roles/cloud-digitalocean/tasks/main.yml`: Added | string filter to user_data
- `files/cloud-init/base.yml`: Replaced write_files with runcmd approach
- Removed complex SSH detection/remediation workaround (no longer needed)
## Benefits
- ✅ Fixes root cause instead of working around symptoms
- ✅ Much simpler and more maintainable code
- ✅ Backward compatible - no API changes required
- ✅ Handles both potential failure modes (encoding + parsing)
- ✅ All tests pass, linters clean
This should resolve DigitalOcean SSH timeout issues while being much
cleaner than the previous workaround approach.
🤖 Generated with [Claude Code](https://claude.ai/code)
Co-Authored-By: Claude <noreply@anthropic.com>
* Fix cloud-init header format for DigitalOcean compatibility
The space in '# cloud-config' (introduced in PR #14775) breaks cloud-init
YAML parsing on DigitalOcean, causing SSH configuration to be skipped.
Cloud-init documentation requires '#cloud-config' without a space.
Fixes#14800🤖 Generated with [Claude Code](https://claude.ai/code)
Co-Authored-By: Claude <noreply@anthropic.com>
* Revert to write_files approach for SSH configuration
Using write_files is more maintainable and Ansible-native than runcmd.
The root cause was the cloud-config header format, not write_files itself.
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Co-Authored-By: Claude <noreply@anthropic.com>
* Fix Ansible deprecation and variable warnings
- Replace deprecated network filters with ansible.utils equivalents:
- ipaddr → ansible.utils.ipaddr
- ipmath → ansible.utils.ipmath
- ipv4 → ansible.utils.ipv4
- ipv6 → ansible.utils.ipv6
- next_nth_usable → ansible.utils.next_nth_usable
- Fix reserved variable name: no_log → algo_no_log
- Fix SSH user groups warning by explicitly specifying groups parameter
Addresses deprecation warnings that would become errors after 2024-01-01.
All linter checks pass with only cosmetic warnings remaining.
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Co-Authored-By: Claude <noreply@anthropic.com>
* Add comprehensive protection for cloud-config header format
- Add inline documentation explaining critical #cloud-config format requirement
- Exclude files/cloud-init/ from yamllint and ansible-lint to prevent automatic 'fixes'
- Create detailed README.md documenting the issue and protection measures
- Reference GitHub issue #14800 for future maintainers
This prevents regression of the critical cloud-init header format that
causes deployment failures when changed from '#cloud-config' to '# cloud-config'.
🤖 Generated with [Claude Code](https://claude.ai/code)
Co-Authored-By: Claude <noreply@anthropic.com>
* Add test for cloud-init header format to prevent regression
This test ensures the cloud-init header remains exactly ''#cloud-config''
without a space. The regression in PR #14775 that added a space broke
DigitalOcean deployments by causing cloud-init YAML parsing to fail,
resulting in SSH timeouts on port 4160.
Co-authored-by: Dan Guido <dguido@users.noreply.github.com>
* Refactor SSH config template and fix MOTD task permissions
- Use dedicated sshd_config template instead of inline content
- Add explicit become: true to MOTD task to fix permissions warning
🤖 Generated with [Claude Code](https://claude.ai/code)
Co-Authored-By: Claude <noreply@anthropic.com>
* Fix no_log variable references after renaming to algo_no_log
Update all remaining references from old 'no_log' variable to 'algo_no_log'
in WireGuard, SSH tunneling, and StrongSwan roles. This fixes deployment
failures caused by undefined variable references.
🤖 Generated with [Claude Code](https://claude.ai/code)
Co-Authored-By: Claude <noreply@anthropic.com>
* fix: Correct YAML indentation in cloud-init template for DigitalOcean
The indent filter was not indenting the first line of the sshd_config content,
causing invalid YAML structure that cloud-init couldn't parse. This resulted
in SSH timeouts during deployment as the port was never changed from 22 to 4160.
- Add first=True parameter to indent filter to ensure all lines are indented
- Remove extra indentation in base template to prevent double-indentation
- Add comprehensive test suite to validate template rendering and prevent regressions
Fixes deployment failures where cloud-init would show:
"Invalid format at line X: expected <block end>, but found '<scalar>'"
🤖 Generated with [Claude Code](https://claude.ai/code)
Co-Authored-By: Claude <noreply@anthropic.com>
---------
Co-authored-by: Claude <noreply@anthropic.com>
Co-authored-by: claude[bot] <209825114+claude[bot]@users.noreply.github.com>
Co-authored-by: Dan Guido <dguido@users.noreply.github.com>
* fix: Remove POSIX-incompatible 'local' keyword from install.sh
The install.sh script uses #\!/usr/bin/env sh (POSIX shell) but was using
the 'local' keyword in the tryGetMetadata function, which is a bash-specific
feature. This caused shellcheck to fail with SC3043 warnings in CI.
Fixed by removing 'local' keywords from variable declarations in the
tryGetMetadata function. The variables are still function-scoped in practice
since they're assigned at the beginning of the function.
This resolves the CI failure introduced in PR #14788 (run #919).
* ci: Make ansible-lint stricter and fix basic issues
- Remove || true from ansible-lint CI job to enforce linting
- Enable name[play] rule - all plays should be named
- Enable yaml[new-line-at-end-of-file] rule
- Move name[missing] from skip_list to warn_list (first step)
- Add names to plays in main.yml and users.yml
- Document future linting improvements in comments
This makes the CI stricter while fixing the easy issues first.
More comprehensive fixes for the 113 name[missing] warnings can
be addressed in future PRs.
* fix: Add name[missing] to skip_list temporarily
The ansible-lint CI is failing because name[missing] was not properly
added to skip_list. This causes 113 name[missing] errors to fail the CI.
Adding it to skip_list for now to fix the CI. The rule can be moved to
warn_list and eventually enabled once all tasks are properly named in
future PRs.
* fix: Fix ansible-lint critical errors
- Fix schema[tasks] error in roles/local/tasks/prompts.yml by removing with_items loop
- Add missing newline at end of requirements.yml
- Replace ignore_errors with failed_when in reboot task
- Add pipefail to shell command with pipes in strongswan openssl task
These fixes address all critical ansible-lint errors that were causing CI failures.
* X.509 Name Constraints
* nameConstraints to a random generated uuid
* Second level domain
* nameConstraints fixes
* critical in nameConstraints lost after last refactoring
<!--- Provide a general summary of your changes in the Title above -->
## Description
Renames the vpn role to strongswan, and split up the variables to support 2 separate VPNs. Closes#1330 and closes#1162
Configures Ansible to use python3 on the server side. Closes#1024
Removes unneeded playbooks, reorganises a lot of variables
Reorganises the `config` folder. Closes#1330
<details><summary>Here is how the config directory looks like now</summary>
<p>
```
configs/X.X.X.X/
|-- ipsec
| |-- apple
| | |-- desktop.mobileconfig
| | |-- laptop.mobileconfig
| | `-- phone.mobileconfig
| |-- manual
| | |-- cacert.pem
| | |-- desktop.p12
| | |-- desktop.ssh.pem
| | |-- ipsec_desktop.conf
| | |-- ipsec_desktop.secrets
| | |-- ipsec_laptop.conf
| | |-- ipsec_laptop.secrets
| | |-- ipsec_phone.conf
| | |-- ipsec_phone.secrets
| | |-- laptop.p12
| | |-- laptop.ssh.pem
| | |-- phone.p12
| | `-- phone.ssh.pem
| `-- windows
| |-- desktop.ps1
| |-- laptop.ps1
| `-- phone.ps1
|-- ssh-tunnel
| |-- desktop.pem
| |-- desktop.pub
| |-- laptop.pem
| |-- laptop.pub
| |-- phone.pem
| |-- phone.pub
| `-- ssh_config
`-- wireguard
|-- desktop.conf
|-- desktop.png
|-- laptop.conf
|-- laptop.png
|-- phone.conf
`-- phone.png
```
</p>
</details>
## Motivation and Context
This refactoring is focused to aim to the 1.0 release
## How Has This Been Tested?
Deployed to several cloud providers with various options enabled and disabled
## Types of changes
<!--- What types of changes does your code introduce? Put an `x` in all the boxes that apply: -->
- [x] Refactoring
## Checklist:
<!--- Go over all the following points, and put an `x` in all the boxes that apply. -->
<!--- If you're unsure about any of these, don't hesitate to ask. We're here to help! -->
- [x] I have read the **CONTRIBUTING** document.
- [x] My code follows the code style of this project.
- [x] My change requires a change to the documentation.
- [x] I have updated the documentation accordingly.
- [x] All new and existing tests passed.
