diff --git a/.github/release-drafter.yml b/.github/release-drafter.yml
index f5c816a08..7dfec8dda 100644
--- a/.github/release-drafter.yml
+++ b/.github/release-drafter.yml
@@ -3,6 +3,9 @@ tag-template: 'Boxed.Templates.$RESOLVED_VERSION'
 change-template: '- $TITLE by @$AUTHOR (#$NUMBER)'
 no-changes-template: '- No changes'
 categories:
+  - title: '📚 Documentation'
+    labels:
+      - 'documentation'
   - title: '📦 ASP.NET Core API Boxed'
     labels:
       - 'template/API'
@@ -39,6 +42,9 @@ template: |
 
   $CONTRIBUTORS
 autolabeler:
+  - label: 'documentation'
+    files:
+      - 'Docs/**/*'
   - label: 'maintenance'
     files:
       - '.github/**/*'
diff --git a/Source/NuGetTemplate/.github/release-drafter.yml b/Source/NuGetTemplate/.github/release-drafter.yml
index 987f83608..f6f00d446 100644
--- a/Source/NuGetTemplate/.github/release-drafter.yml
+++ b/Source/NuGetTemplate/.github/release-drafter.yml
@@ -9,6 +9,9 @@ tag-template: '$RESOLVED_VERSION'
 change-template: '- $TITLE by @$AUTHOR (#$NUMBER)'
 no-changes-template: '- No changes'
 categories:
+  - title: '📚 Documentation'
+    labels:
+      - 'documentation'
   - title: '🚀 New Features'
     labels:
       - 'enhancement'
@@ -35,3 +38,17 @@ template: |
   ## 👨🏼‍💻 Contributors
 
   $CONTRIBUTORS
+autolabeler:
+  - label: 'documentation'
+    files:
+      - '**/*.md'
+  - label: 'enhancement'
+    files:
+      - 'Source/**/*'
+  - label: 'maintenance'
+    files:
+#if (GitHub)
+      - '.github/**/*'
+#endif
+      - 'Images/**/*'
+      - 'Tests/**/*'
\ No newline at end of file