diff --git a/.github/workflows/insert-checklist.yml b/.github/workflows/insert-checklist.yml
new file mode 100644
index 0000000..e329d04
--- /dev/null
+++ b/.github/workflows/insert-checklist.yml
@@ -0,0 +1,50 @@
+name: ☑️ Generate and insert markdown from YAML
+
+on:
+  workflow_dispatch:
+  push:
+    branches: [ main ]
+    paths: ['personal-security-checklist.yml']
+    
+jobs:
+  build:
+    runs-on: ubuntu-latest
+
+    steps:
+      - name: Checkout repository 🛎️
+        uses: actions/checkout@v2
+        
+      # Get current date-time (used for commit message)
+      - name: Get Date 📅
+        id: date
+        run: echo "::set-output name=date::$(date +'%d-%b-%Y')"
+        
+      # Downloads + installs Python (used for running gen scripts)  
+      - name: Set up Python 🐍
+        uses: actions/setup-python@v2
+        with:
+          python-version: '3.x'
+          
+      # Install contents of requirements.txt
+      - name: Install dependencies 📥
+        run: |
+          python -m pip install --upgrade pip
+          cd lib && pip install -r requirements.txt
+
+      # The make command triggers all the Python scripts, generates output
+      - name: Run make command 🔨
+        run: python lib/generate.py
+
+      # Commit and push the outputed JSON files
+      - name: Commit and push generated files ⤴️
+        run: |
+          git config --global user.name "Liss-Bot"
+          git config --global user.email "alicia-gh-bot@mail.as93.net"
+          git pull origin main
+          git add CHECKLIST.md
+          if git diff --staged --quiet; then
+            echo "Nothin new added, so nothing to commit, exiting..."
+          else
+            git commit -m "Updates checklist (auto-generated, on ${{ steps.date.outputs.date }})"
+            git push
+          fi
diff --git a/lib/generate.py b/lib/generate.py
index e69de29..b345a06 100644
--- a/lib/generate.py
+++ b/lib/generate.py
@@ -0,0 +1,65 @@
+import os
+import yaml
+import logging
+
+# Configure Logging
+logging.basicConfig(level=logging.INFO)
+logger = logging.getLogger(__name__)
+
+project_root = os.path.dirname(os.path.dirname(os.path.abspath(__file__)))
+yaml_file_path = os.path.join(project_root, 'personal-security-checklist.yml')
+markdown_file_path = os.path.join(project_root, 'CHECKLIST.md')
+
+
+def read_yaml(file_path):
+    logger.info(f"Reading YAML file from {file_path}...")
+    with open(file_path, 'r') as file:
+        return yaml.safe_load(file)
+
+def generate_markdown_section(section):
+    markdown = f"## {section['title']}\n\n"
+    markdown += f"{section['intro']}\n\n"
+    markdown += "**Security** | **Priority** | **Details and Hints**\n"
+    markdown += "--- | --- | ---\n"
+    for item in section['checklist']:
+        markdown += f"**{item['point']}** | {item['priority']} | {item['details']}\n"
+    
+    if 'softwareLinks' in section:
+        software_links = [software for software in section['softwareLinks'] if 'title' in software and 'url' in software]
+        if software_links:
+            markdown += "\n### Recommended Software\n"
+            for software in software_links:
+                markdown += f"- [{software['title']}]({software['url']})\n"
+    
+    return markdown
+
+def insert_markdown_content(md_file_path, new_content):
+    start_marker, end_marker = "<!-- checklist-start -->", "<!-- checklist-end -->"
+    logger.info(f"Inserting generated markdown into {md_file_path} between markers...")
+    
+    with open(md_file_path, 'r') as file:
+        content = file.read()
+    
+    start_index = content.find(start_marker)
+    end_index = content.find(end_marker, start_index)
+    
+    if start_index == -1 or end_index == -1:
+        logger.error("Markers not found in the markdown file.")
+        return
+    
+    updated_content = content[:start_index + len(start_marker)] + "\n" + new_content + "\n" + content[end_index:]
+    
+    with open(md_file_path, 'w') as file:
+        file.write(updated_content)
+    logger.info("Markdown content successfully inserted.")
+
+def main():
+    yaml_data = read_yaml(yaml_file_path)
+    markdown_content = ""
+    for section in yaml_data:
+        markdown_content += generate_markdown_section(section) + "\n\n"
+    insert_markdown_content(markdown_file_path, markdown_content)
+    logger.info("Script completed successfully!")
+
+if __name__ == "__main__":
+    main()
diff --git a/lib/requirements.txt b/lib/requirements.txt
new file mode 100644
index 0000000..b369901
--- /dev/null
+++ b/lib/requirements.txt
@@ -0,0 +1,2 @@
+PyYAML==6.0.1
+requests==2.31.0