diff --git a/MILESTONES.md b/MILESTONES.md
index 10ddc3e4..71dfd4a9 100644
--- a/MILESTONES.md
+++ b/MILESTONES.md
@@ -27,9 +27,18 @@ DocuElevate follows [Semantic Versioning 2.0.0](https://semver.org/):
 - **Database-backed settings management with encryption**
 - **Setup wizard for first-time configuration**
 - **Admin UI for runtime configuration**
+- **Automated semantic versioning and releases**
 - OAuth2 authentication with admin group support
 - Basic web UI and REST API
 
+### Important Note on Versioning
+As of February 2026, DocuElevate uses **automated semantic versioning**:
+- Version management handled by `python-semantic-release`
+- Releases automated via GitHub Actions on merge to main
+- Version bumps determined by conventional commit messages
+- `VERSION` and `CHANGELOG.md` automatically updated
+- GitHub Releases created automatically with release notes
+
 ---
 
 ## Previous Releases
@@ -237,7 +246,27 @@ This is our first major release, marking production-ready enterprise capabilitie
 
 ## Release Process
 
-### Pre-release Checklist
+### Automated Semantic Versioning (v0.6.0+)
+Starting with v0.6.0, releases are fully automated using `python-semantic-release`:
+
+1. **Commit with Conventional Format**: Use conventional commit messages (feat, fix, etc.)
+2. **Merge to Main**: PR merges trigger semantic-release workflow
+3. **Automated Analysis**: semantic-release determines version from commits
+4. **Automatic Updates**:
+   - Updates `VERSION` file
+   - Generates/updates `CHANGELOG.md`
+   - Creates Git tag (e.g., `v0.6.0`)
+   - Creates GitHub Release with notes
+   - Triggers Docker image builds
+5. **No Manual Steps**: VERSION and CHANGELOG are never edited manually
+
+### Version Bump Rules
+- `feat:` commits → Minor version (0.5.0 → 0.6.0)
+- `fix:`, `perf:` → Patch version (0.5.0 → 0.5.1)
+- `feat!:`, `BREAKING CHANGE:` → Major version (0.5.0 → 1.0.0)
+- Other types (docs, chore, etc.) → No version bump
+
+### Pre-release Checklist (Automated)
 - [ ] All tests passing
 - [ ] Security scan passed
 - [ ] Code review completed
diff --git a/ROADMAP.md b/ROADMAP.md
index e121b8ce..389693fe 100644
--- a/ROADMAP.md
+++ b/ROADMAP.md
@@ -46,6 +46,12 @@ DocuElevate aims to be the premier open-source intelligent document processing p
   - [ ] Implement API key rotation
   - [ ] Add audit logging for sensitive operations
 
+- **Release Automation** (Completed ✅)
+  - [x] Implement semantic-release for automated versioning
+  - [x] Add conventional commit validation
+  - [x] Automate CHANGELOG generation
+  - [x] Integrate Docker builds with releases
+
 ### Features - v0.4.0
 - **Enhanced Search & Filtering**
   - [ ] Full-text search across documents
diff --git a/TODO.md b/TODO.md
index 7f735a8e..4042e3cf 100644
--- a/TODO.md
+++ b/TODO.md
@@ -7,6 +7,15 @@ This document tracks actionable tasks for the current development cycle. For lon
 
 ---
 
+## ⚠️ Important Note on Versioning
+
+As of this update, DocuElevate uses **automated semantic versioning** via `python-semantic-release`:
+- **DO NOT** manually edit `VERSION` or `CHANGELOG.md` 
+- Version bumps are automated based on conventional commit messages
+- See [CONTRIBUTING.md](CONTRIBUTING.md) for commit message format
+
+---
+
 ## 🔴 Critical Priority (This Week)
 
 ### Security
@@ -46,6 +55,8 @@ This document tracks actionable tasks for the current development cycle. For lon
 - [x] Enable tests in GitHub Actions
 - [x] Add coverage reporting
 - [x] Add CodeQL scanning
+- [x] Implement semantic-release for automated versioning
+- [x] Add conventional commit validation (commitlint)
 - [ ] Add dependency scanning (Dependabot or similar)
 - [ ] Make linting checks blocking (once critical issues fixed)
 - [ ] Add build status badges to README.md
@@ -55,8 +66,9 @@ This document tracks actionable tasks for the current development cycle. For lon
 - [x] Create MILESTONES.md
 - [x] Create TODO.md
 - [x] Create SECURITY_AUDIT.md
-- [ ] Create AGENTIC_CODING.md
-- [ ] Update CONTRIBUTING.md with testing guidelines
+- [x] Create AGENTIC_CODING.md
+- [x] Update CONTRIBUTING.md with testing guidelines and conventional commits
+- [x] Archive one-off documentation files to docs/archive/
 - [ ] Add architecture diagram to docs/
 - [ ] Document all environment variables in docs/ConfigurationGuide.md
 - [ ] Add troubleshooting section for common test failures
@@ -214,7 +226,18 @@ This document tracks actionable tasks for the current development cycle. For lon
 
 ## ✅ Completed (Recent)
 
-### 2026-02-08
+### 2026-02-08 (Semantic Release & Documentation Overhaul)
+- [x] Implemented semantic-release with python-semantic-release
+- [x] Created pyproject.toml with semantic-release configuration
+- [x] Added .github/workflows/release.yml for automated releases
+- [x] Added conventional commit validation (commitlint) to pre-commit hooks
+- [x] Updated Docker workflow to use docuelevate image name
+- [x] Archived one-off documentation to docs/archive/
+- [x] Updated CONTRIBUTING.md with conventional commits guide
+- [x] Updated AGENTIC_CODING.md with versioning/release process
+- [x] Updated .github/copilot-instructions.md with commit format rules
+
+### 2026-02-08 (Settings Management)
 - [x] Implemented database-backed settings management system
 - [x] Added Fernet encryption for sensitive settings in database
 - [x] Created 3-step setup wizard for fresh installations