docs: add known issues documentation for Darwin 15.5 upgrade issue

Documents the self-upgrade issue on macOS Darwin 15.5 affecting
ctrld v1.4.2+ and provides workarounds for affected users.

docs/known-issues.md

@@ -0,0 +1,42 @@
+# Known Issues
+
+This document outlines known issues with ctrld and their current status, workarounds, and recommendations.
+
+## macOS (Darwin) Issues
+
+### Self-Upgrade Issue on Darwin 15.5
+
+**Issue**: ctrld self-upgrading functionality may not work on macOS Darwin 15.5.
+
+**Status**: Under investigation
+
+**Description**: Users on macOS Darwin 15.5 may experience issues when ctrld attempts to perform automatic self-upgrades. The upgrade process would be triggered, but ctrld won't be upgraded.
+
+**Workarounds**:
+1. **Recommended**: Upgrade your macOS system to Darwin 15.6 or later, which has been tested and verified to work correctly with ctrld self-upgrade functionality.
+2. **Alternative**: Run `ctrld upgrade prod` directly to manually upgrade ctrld to the latest version on Darwin 15.5.
+
+**Affected Versions**: ctrld v1.4.2 and later on macOS Darwin 15.5
+
+**Last Updated**: 05/09/2025
+
+---
+
+## Contributing to Known Issues
+
+If you encounter an issue not listed here, please:
+
+1. Check the [GitHub Issues](https://github.com/Control-D-Inc/ctrld/issues) to see if it's already reported
+2. If not reported, create a new issue with:
+   - Detailed description of the problem
+   - Steps to reproduce
+   - Expected vs actual behavior
+   - System information (OS, version, architecture)
+   - ctrld version
+
+## Issue Status Legend
+
+- **Under investigation**: Issue is confirmed and being analyzed
+- **Workaround available**: Temporary solution exists while permanent fix is developed
+- **Fixed**: Issue has been resolved in a specific version
+- **Won't fix**: Issue is acknowledged but will not be addressed due to technical limitations or design decisions