diff --git a/.chglog/CHANGELOG.tpl.md b/.chglog/CHANGELOG.tpl.md
new file mode 100755
index 00000000000..c2b5a55cdb4
--- /dev/null
+++ b/.chglog/CHANGELOG.tpl.md
@@ -0,0 +1,56 @@
+{{ if .Versions -}}
+<a name="unreleased"></a>
+## [Unreleased]
+
+{{ if .Unreleased.CommitGroups -}}
+{{ range .Unreleased.CommitGroups -}}
+### {{ .Title }}
+{{ range .Commits -}}
+- {{ if .Scope }}**{{ .Scope }}:** {{ end }}{{ .Subject }}
+{{ end }}
+{{ end -}}
+{{ end -}}
+{{ end -}}
+
+{{ range .Versions }}
+<a name="{{ .Tag.Name }}"></a>
+## {{ if .Tag.Previous }}[{{ .Tag.Name }}]{{ else }}{{ .Tag.Name }}{{ end }} - {{ datetime "2006-01-02" .Tag.Date }}
+{{ range .CommitGroups -}}
+### {{ .Title }}
+{{ range .Commits -}}
+- {{ if .Scope }}**{{ upperFirst .Scope }}:** {{ end }}{{ .Subject }}
+{{ end }}
+{{ end -}}
+
+{{- if .RevertCommits -}}
+### Reverts
+{{ range .RevertCommits -}}
+- {{ .Revert.Header }}
+{{ end }}
+{{ end -}}
+
+{{- if .MergeCommits -}}
+### Pull Requests
+{{ range .MergeCommits -}}
+- {{ .Header }}
+{{ end }}
+{{ end -}}
+
+{{- if .NoteGroups -}}
+{{ range .NoteGroups -}}
+### {{ .Title }}
+{{ range .Notes }}
+{{ .Body }}
+{{ end }}
+{{ end -}}
+{{ end -}}
+{{ end -}}
+
+{{- if .Versions }}
+[Unreleased]: {{ .Info.RepositoryURL }}/compare/{{ $latest := index .Versions 0 }}{{ $latest.Tag.Name }}...HEAD
+{{ range .Versions -}}
+{{ if .Tag.Previous -}}
+[{{ .Tag.Name }}]: {{ $.Info.RepositoryURL }}/compare/{{ .Tag.Previous.Name }}...{{ .Tag.Name }}
+{{ end -}}
+{{ end -}}
+{{ end -}}
diff --git a/.chglog/config.yml b/.chglog/config.yml
new file mode 100755
index 00000000000..294b3289981
--- /dev/null
+++ b/.chglog/config.yml
@@ -0,0 +1,32 @@
+style: github
+template: CHANGELOG.tpl.md
+info:
+  title: CHANGELOG
+  repository_url: https://github.com/awslabs/aws-lambda-powertools-python
+options:
+  commits:
+    filters:
+      Type:
+        - feat
+        - fix
+        - perf
+        - refactor
+        - docs
+        - chore
+  commit_groups:
+    title_maps:
+      feat: Features
+      fix: Bug Fixes
+      perf: Performance Improvements
+      refactor: Code Refactoring
+      docs: Documentation
+      chore: Project maintenance
+  header:
+    pattern: "^(\\w*)(?:\\(([\\w\\$\\.\\-\\*\\s]*)\\))?\\:\\s(.*)$"
+    pattern_maps:
+      - Type
+      - Scope
+      - Subject
+  notes:
+    keywords:
+      - BREAKING CHANGE
diff --git a/.github/auto-label.json b/.github/auto-label.json
deleted file mode 100644
index 1218790bdc4..00000000000
--- a/.github/auto-label.json
+++ /dev/null
@@ -1,10 +0,0 @@
-{
-  "rules": {
-    "area/utilities": ["aws_lambda_powertools_python/utilities/", "aws_lambda_powertools_python/utilities/", "aws_lambda_powertools_python/middleware_factory/"],
-    "area/logger": ["aws_lambda_powertools_python/logging/"],
-    "area/tracer": ["aws_lambda_powertools_python/tracing/"],
-    "area/metrics": ["aws_lambda_powertools_python/metrics/"],
-    "documentation": ["docs/", "mkdocs.yml"],
-    "internal": ["Makefile", "CHANGELOG.md", "CONTRIBUTING.md"]
-  }
-}
diff --git a/.github/boring-cyborg.yml b/.github/boring-cyborg.yml
index 89d93b17e37..f79494d01aa 100644
--- a/.github/boring-cyborg.yml
+++ b/.github/boring-cyborg.yml
@@ -1,21 +1,52 @@
 ##### Labeler ##########################################################################################################
 labelPRBasedOnFilePath:
   area/utilities:
+    - aws_lambda_powertools/utilities/*
     - aws_lambda_powertools/utilities/**/*
+    - aws_lambda_powertools_python/middleware_factory/*
+    - aws_lambda_powertools_python/middleware_factory/**/*
+  area/logger:
+    - aws_lambda_powertools_python/logging/*
+    - aws_lambda_powertools_python/logging/**/*
+    - aws_lambda_powertools_python/package_logger.py
+  area/tracer:
+    - aws_lambda_powertools_python/tracing/*
+    - aws_lambda_powertools_python/tracing/**/*
+  area/metrics:
+    - aws_lambda_powertools_python/metrics/*
+    - aws_lambda_powertools_python/metrics/**/*
+  area/event_handlers:
+    - aws_lambda_powertools_python/event_handler/*
+    - aws_lambda_powertools_python/event_handler/**/*
 
-  # Add 'label2' to any file changes within 'example2' folder
   documentation:
     - docs/*
     - docs/**/*
+    - mkdocs.yml
 
-#  # Complex: Add 'area/core' label to any change within the 'core' package
-#  area/core:
-#    - src/core/*
-#    - src/core/**/*
-#
-#  # Add 'test' label to any change to *.spec.js files within the source dir
-#  test:
-#    - src/**/*.spec.js
+  internal:
+    - .github/*
+    - .github/**/*
+    - .chglog/*
+    - .flake8
+    - .gitignore
+    - .pre-commit-config.yaml
+    - Makefile
+    - CONTRIBUTING.md
+    - CODE_OF_CONDUCT.md
+    - LICENSE
+    - aws_lambda_powertools_python/shared/*
+    - aws_lambda_powertools_python/shared/**
+
+  dependencies:
+    - pyproject.toml
+    - poetry.lock
+
+  tests:
+    - tests/*
+    - tests/**/*
+    - benchmark/*
+    - benchmark/**/*
 
 ##### Greetings ########################################################################################################
 firstPRWelcomeComment: >
diff --git a/.github/workflows/publish.yml b/.github/workflows/publish.yml
index 246992ec244..42eeae4b0f0 100644
--- a/.github/workflows/publish.yml
+++ b/.github/workflows/publish.yml
@@ -4,7 +4,7 @@ name: Publish to PyPi
 #
 # === Manual activities ===
 #
-# 1. Document human readable changes in CHANGELOG
+# 1. Document human readable changes in CHANGELOG (pre-generate unreleased changes with `make changelog`)
 # 2. Bump package version using poetry version <major|minor|patch|specific version>
 # 3. Merge version changes to develop branch
 # 4. Edit the current draft release notes
diff --git a/.gitignore b/.gitignore
index ace70c8192d..ce5e32bd3e1 100644
--- a/.gitignore
+++ b/.gitignore
@@ -295,6 +295,7 @@ test_report
 wheelhouse
 /.idea/*
 *.html
+TMP_CHANGELOG.md
 
 # Docs files
 docs/.cache/
diff --git a/Makefile b/Makefile
index b0a075d39a2..018f9c9420d 100644
--- a/Makefile
+++ b/Makefile
@@ -79,3 +79,7 @@ release: pr
 	poetry build
 	$(MAKE) release-test
 	$(MAKE) release-prod
+
+changelog:
+	 @echo "[+] Pre-generating CHANGELOG for tag: $$(git describe --abbrev=0 --tag)"
+	 docker run -v ${PWD}:/workdir quay.io/git-chglog/git-chglog $$(git describe --abbrev=0 --tag).. -o TMP_CHANGELOG.md