diff --git a/.circleci/config.yml b/.circleci/config.yml
index 4286abde9..1bacee3e9 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -233,11 +233,6 @@ jobs:
           command: |
             python3 ${CI_SCRIPTS_DIR}/bump-part.py
 
-      - run:
-          name: Update Changelog entries
-          command: |
-            python3 ${CI_SCRIPTS_DIR}/update-changelog.py
-
   # Publish a wheel and tarball of the Scenario Player to pypi.
   deploy-to-pypi:
     executor: default-executor
diff --git a/.circleci/scripts/bump-part.py b/.circleci/scripts/bump-part.py
index a08dd7920..abc9b30db 100755
--- a/.circleci/scripts/bump-part.py
+++ b/.circleci/scripts/bump-part.py
@@ -12,6 +12,7 @@
     REPO_NAME,
     REPO_OWNER,
 )
+from chlogger import make_chlog
 
 from scenario_player import __version__
 
@@ -65,6 +66,7 @@ def get_last_tag():
                 part = "minor"
                 break
 
+
 print(f"Bumping part {part}..")
 
 
@@ -85,6 +87,11 @@ def get_last_tag():
         stdout=subprocess.PIPE,
     )
 
+if CURRENT_BRANCH == "master" and COMMIT_TYPE == "RELEASE":
+    r = subprocess.run(f"git --git-dir={PROJECT_GIT_DIR} describe --abbrev=0 --tags", check=True)
+    tag = r.stdout.decode("UTF-8").strip(" ").strip("\n")
+    make_chlog(Path(f"{PROJECT_ROOT}/CHANGES.rst"), new_version=tag)
+
 print("Push Bump commit..")
 subprocess.run(
     f"git --git-dir={PROJECT_GIT_DIR} push --set-upstream origin {CURRENT_BRANCH}".split(" "),
diff --git a/.circleci/scripts/chlogger.py b/.circleci/scripts/chlogger.py
new file mode 100644
index 000000000..44a0cfd1a
--- /dev/null
+++ b/.circleci/scripts/chlogger.py
@@ -0,0 +1,137 @@
+import pathlib
+import re
+import subprocess
+
+from typing import List, Tuple
+from constants import PROJECT_GIT_DIR, CURRENT_BRANCH, COMMIT_PATTERN, COMMIT_TYPE
+
+
+def read_git_commit_history_since_tag(
+        tag
+    ) -> Tuple[List[Tuple[str, str]], List[Tuple[str, str]], List[Tuple[str, str]]]:
+    """Return a list of all git commit titles since the given `tag`.
+
+    If `tag` is not given, we'll use the previous tag and compare the log up
+    up to the current tag.
+
+    The commits are returned as three lists:
+        1. feature commits
+        2. bugfix commits
+        3. hotfix commits
+    """
+    completed_process = subprocess.run(
+        f"git --git-dir={PROJECT_GIT_DIR} log {tag}..master --format=%s".split(" "),
+        check=True,
+        stdout=subprocess.PIPE,
+    )
+    titles = completed_process.stdout.decode("UTF-8").split("\n")
+
+    # The body of a commit may include newline characters, so we need to specify
+    # a custom separator to indicate the end of the commit body.
+    separator = "<><><>"
+    completed_process = subprocess.run(
+        f"git --git-dir={PROJECT_GIT_DIR} log {tag}..master --format=%b{separator}".split(" "),
+        check=True,
+        stdout=subprocess.PIPE,
+    )
+    bodies = completed_process.stdout.decode("UTF-8").split(separator)
+
+    assert len(titles) == len(bodies)
+
+    pattern = re.compile(COMMIT_PATTERN)
+
+    feats, fixes, hotfixes = [], [], []
+
+    for title, body in zip(titles, bodies):
+        match = pattern.match(title)
+        if not match:
+            continue
+
+        commit_type = match.groupdict()["TYPE"]
+
+        if commit_type == "FEAT":
+            feats.append((title, body))
+        elif commit_type == "FIX":
+            fixes.append((title, body))
+        elif commit_type == "HOTFIX":
+            hotfixes.append((title, body))
+        else:
+            print(f"No type found, skipping commit '{title}'..")
+
+    return feats, fixes, hotfixes
+
+
+def format_commits(commits: List[Tuple[str, str]]) -> List[str]:
+    """Format the given commits for writing to the Changelog.
+
+    The expected input Tuple[str, str] format is:
+
+        ([(FEAT|FIX|HOTFIX)-#123] <Subject>, <Optional body with further details on the commit.>)
+
+    The output format is as follows::
+
+        r'- #123 <Subject>\n    <Optional body with further details on the commit.>\n'
+
+    Newlines in the body are honored, and each line indented by 4 spaces automatically.
+    TODO: Duplicate Issues should share a single Changelog Entry.
+    """
+    if not commits:
+        return []
+    pattern = re.compile(COMMIT_PATTERN)
+    formatted = set()
+    for title, body in commits:
+        match = pattern.match(title)
+        issue, subject = match.groupdict()["ISSUE"], match.groupdict()["SUBJECT"]
+
+        entry = f"- {issue} {subject}\n"
+
+        if body:
+            # Make sure the body is indented by 8 spaces.
+            formatted_body = "        ".join(body.split("\n"))
+            entry += f"{formatted_body}\n"
+        formatted.add(entry)
+    return sorted(formatted)
+
+
+def update_chlog(
+        tag: str,
+        feats: List[str],
+        fixes: List[str],
+        hotfixes: List[str],
+        chlog_path: pathlib.Path = pathlib.Path("CHANGELOG.rst"),
+):
+    try:
+        history = chlog_path.read_text()
+    except FileNotFoundError:
+        print("No Changelog file found - creating a new one.")
+        history = ""
+
+    chlog_entry = f"RELEASE {tag}\n=============\n\n"
+
+    if feats:
+        feats = "\n".join(feats)
+        chlog_entry += f"Features\n--------\n{feats}\n"""
+
+    if fixes:
+        fixes = "\n".join(fixes)
+
+        chlog_entry += f"Fixes\n-----\n{fixes}\n"
+
+    if hotfixes:
+        hotfixes = "\n".join(hotfixes)
+
+        chlog_entry += f"Hotfixes\n--------\n{hotfixes}\n"
+    chlog_path.write_text(f"{chlog_entry}\n{history}")
+
+
+def make_chlog(chlog_path, new_version):
+    feats, fixes, hotfixes = read_git_commit_history_since_tag(new_version)
+    update_chlog(
+        "0.4.0", format_commits(feats), format_commits(fixes), format_commits(hotfixes), chlog_path
+    )
+
+    subprocess.run(f"git --git-dir={PROJECT_GIT_DIR} git add CHANGELOG.rst".split(" "), check=True)
+    subprocess.run(
+        f"git --git-dir={PROJECT_GIT_DIR} git commit CHANGELOG.rst -m \"Update Changelog.\"".split(" "),
+        check=True
+    )
diff --git a/.circleci/scripts/constants.py b/.circleci/scripts/constants.py
index 342c2bfca..30e6893d5 100644
--- a/.circleci/scripts/constants.py
+++ b/.circleci/scripts/constants.py
@@ -9,7 +9,7 @@
 PROJECT_ROOT = os.environ["PROJECT_ROOT"]
 COMMIT_SHA = os.environ["CIRCLE_SHA1"]
 
-COMMIT_PATTERN = r"^\[(?P<TYPE>(FEAT|FIX|HOTFIX))-(?P<ISSUE>#\d+)\]\w?(?P<SUBJECT>)"
+COMMIT_PATTERN = r"^\[(?P<TYPE>(FEAT|FIX|HOTFIX))-(?P<ISSUE>#\d+)\]\w?(?P<SUBJECT>.*$)"
 RELEASE_COMMIT_PATTERN = r"^\[(?P<TYPE>RELEASE)\]\w?(?P<SUBJECT>)"
 BUMPVERSION_PREFIX = "Cut New Release:"
 CURRENT_BRANCH = os.environ.get("CIRCLE_BRANCH")
diff --git a/.circleci/scripts/update-changelog.py b/.circleci/scripts/update-changelog.py
deleted file mode 100644
index 6b92746c7..000000000
--- a/.circleci/scripts/update-changelog.py
+++ /dev/null
@@ -1,51 +0,0 @@
-"""TODO: This script is a stub."""
-from typing import List, Tuple
-from constants import PROJECT_GIT_DIR, CURRENT_BRANCH
-
-
-if CURRENT_BRANCH != "master":
-    exit(0)
-
-
-def read_git_commit_history_since_tag(tag=None) -> Tuple[List[str], List[str], List[str]]:
-    """Return a list of all git commit titles since the given `tag`.
-
-    If `tag` is not given, we'll use the previous tag and compare the log up
-    up to the current tag.
-
-    The commits are returned as three lists:
-        feature commits
-        2. bugfix commits
-        3. hotfix commits
-    """
-    completed_process = subprocess.run(
-        f"git --git-dir={PROJECT_GIT_DIR} log master..release --format=%s".split(" "),
-        check=True,
-        stdout=subprocess.PIPE,
-    )
-    titles = completed_process.stdout.decode("UTF-8").split("\n")
-
-    completed_process = subprocess.run(
-        f"git --git-dir={PROJECT_GIT_DIR} log master..release --format=%b".split(" "),
-        check=True,
-        stdout=subprocess.PIPE,
-    )
-    bodies = completed_process.stdout.decode("UTF-8").split("\n")
-
-
-def format_commits(*commits) -> List[str]:
-    """Format the given commits for writing to the Changelog.
-
-    The expected input str format is:
-
-        [(FEAT|FIX|HOTFIX)-#123] <Subject>
-
-        <Optional body with further details on the commit.>
-
-    The output format is as follows::
-
-        - #123 <Subject>
-            <Optional body with further details on the commit.>
-
-    """
-