diff --git a/.github/CODEOWNERS b/.github/CODEOWNERS
index 496e05e233a..74bdd4be963 100644
--- a/.github/CODEOWNERS
+++ b/.github/CODEOWNERS
@@ -58,6 +58,7 @@
 /code/modules/preferences_menu.dm @Mothblocks
 /code/modules/preferences_savefile.dm @Mothblocks
 /tgui/packages/tgui/interfaces/PreferencesMenu/ @Mothblocks
+/tools/pull_request_hooks/ @Mothblocks
 /tools/screenshot-test-comparison/ @Mothblocks
 /tools/test_merge_bot/ @Mothblocks
 
diff --git a/.github/workflows/auto_changelog.yml b/.github/workflows/auto_changelog.yml
new file mode 100644
index 00000000000..cb7c073f5cb
--- /dev/null
+++ b/.github/workflows/auto_changelog.yml
@@ -0,0 +1,23 @@
+# Creates an entry in html/changelogs automatically, to eventually be compiled by compile_changelogs
+name: Auto Changelog
+on:
+  pull_request_target:
+    types:
+      - closed
+    branches:
+      - master
+permissions:
+  contents: write
+jobs:
+  auto_labeler:
+    runs-on: ubuntu-latest
+    if: github.event.pull_request.merged == true
+    steps:
+    - name: Checkout
+      uses: actions/checkout@v3
+    - name: Run auto labeler
+      uses: actions/github-script@v6
+      with:
+        script: |
+          const { processAutoChangelog } = await import('${{ github.workspace }}/tools/pull_request_hooks/autoChangelog.js')
+          await processAutoChangelog({ github, context })
diff --git a/tools/WebhookProcessor/github_webhook_processor.php b/tools/WebhookProcessor/github_webhook_processor.php
index 4ee4dba83c7..2c3f60ec9ad 100644
--- a/tools/WebhookProcessor/github_webhook_processor.php
+++ b/tools/WebhookProcessor/github_webhook_processor.php
@@ -240,7 +240,7 @@ function tag_pr($payload, $opened) {
 	$tags = array();
 	$title = $payload['pull_request']['title'];
 	if($opened) {	//you only have one shot on these ones so as to not annoy maintainers
-		$tags = checkchangelog($payload, false);
+		$tags = checkchangelog($payload);
 
 		if(strpos(strtolower($title), 'refactor') !== FALSE)
 			$tags[] = 'Refactor';
@@ -302,7 +302,7 @@ function check_dismiss_changelog_review($payload){
 		return;
 
 	if(!$no_changelog)
-		checkchangelog($payload, false);
+		checkchangelog($payload);
 
 	$review_message = 'Your changelog for this PR is either malformed or non-existent. Please create one to document your changes.';
 
@@ -362,7 +362,7 @@ function handle_pr($payload) {
 			else {
 				$action = 'merged';
 				auto_update($payload);
-				checkchangelog($payload, true);
+				checkchangelog($payload);
 				$validated = TRUE; //pr merged events always get announced.
 			}
 			break;
@@ -630,7 +630,7 @@ function has_tree_been_edited($payload, $tree){
 }
 
 $no_changelog = false;
-function checkchangelog($payload, $compile = true) {
+function checkchangelog($payload) {
 	global $no_changelog;
 	if (!isset($payload['pull_request']) || !isset($payload['pull_request']['body'])) {
 		return;
@@ -648,26 +648,16 @@ function checkchangelog($payload, $compile = true) {
 	$body = str_replace("\r\n", "\n", $body);
 	$body = explode("\n", $body);
 
-	$username = $payload['pull_request']['user']['login'];
 	$incltag = false;
-	$changelogbody = array();
-	$currentchangelogblock = array();
 	$foundcltag = false;
 	foreach ($body as $line) {
 		$line = trim($line);
 		if (substr($line,0,4) == ':cl:' || substr($line,0,1) == '??') {
 			$incltag = true;
 			$foundcltag = true;
-			$pos = strpos($line, " ");
-			if ($pos) {
-				$tmp = substr($line, $pos+1);
-				if (trim($tmp) != 'optional name here')
-					$username = $tmp;
-			}
 			continue;
 		} else if (substr($line,0,5) == '/:cl:' || substr($line,0,6) == '/ :cl:' || substr($line,0,5) == ':/cl:' || substr($line,0,5) == '/??' || substr($line,0,6) == '/ ??' ) {
 			$incltag = false;
-			$changelogbody = array_merge($changelogbody, $currentchangelogblock);
 			continue;
 		}
 		if (!$incltag)
@@ -683,47 +673,44 @@ function checkchangelog($payload, $compile = true) {
 			$firstword = $line;
 		}
 
+		// Line is empty
 		if (!strlen($firstword)) {
-			if (count($currentchangelogblock) <= 0)
-				continue;
-			$currentchangelogblock[count($currentchangelogblock)-1]['body'] .= "\n";
 			continue;
 		}
+
 		//not a prefix line.
-		//so we add it to the last changelog entry as a separate line
 		if (!strlen($firstword) || $firstword[strlen($firstword)-1] != ':') {
-			if (count($currentchangelogblock) <= 0)
-				continue;
-			$currentchangelogblock[count($currentchangelogblock)-1]['body'] .= "\n".$line;
 			continue;
 		}
+
 		$cltype = strtolower(substr($firstword, 0, -1));
+
+		// !!!
+		// !!! If you are changing any of these at the bottom, also edit `tools/pull_request_hooks/changelogConfig.js`.
+		// !!!
+
 		switch ($cltype) {
 			case 'fix':
 			case 'fixes':
 			case 'bugfix':
 				if($item != 'fixed a few things') {
 					$tags[] = 'Fix';
-					$currentchangelogblock[] = array('type' => 'bugfix', 'body' => $item);
 				}
 				break;
 			case 'qol':
 				if($item != 'made something easier to use') {
 					$tags[] = 'Quality of Life';
-					$currentchangelogblock[] = array('type' => 'qol', 'body' => $item);
 				}
 				break;
 			case 'soundadd':
 				if($item != 'added a new sound thingy') {
 					$tags[] = 'Sound';
-					$currentchangelogblock[] = array('type' => 'soundadd', 'body' => $item);
 				}
 				break;
 			case 'sounddel':
 				if($item != 'removed an old sound thingy') {
 					$tags[] = 'Sound';
 					$tags[] = 'Removal';
-					$currentchangelogblock[] = array('type' => 'sounddel', 'body' => $item);
 				}
 				break;
 			case 'add':
@@ -731,7 +718,6 @@ function checkchangelog($payload, $compile = true) {
 			case 'rscadd':
 				if($item != 'Added new mechanics or gameplay changes' && $item != 'Added more things') {
 					$tags[] = 'Feature';
-					$currentchangelogblock[] = array('type' => 'rscadd', 'body' => $item);
 				}
 				break;
 			case 'del':
@@ -739,95 +725,53 @@ function checkchangelog($payload, $compile = true) {
 			case 'rscdel':
 				if($item != 'Removed old things') {
 					$tags[] = 'Removal';
-					$currentchangelogblock[] = array('type' => 'rscdel', 'body' => $item);
 				}
 				break;
 			case 'imageadd':
 				if($item != 'added some icons and images') {
 					$tags[] = 'Sprites';
-					$currentchangelogblock[] = array('type' => 'imageadd', 'body' => $item);
 				}
 				break;
 			case 'imagedel':
 				if($item != 'deleted some icons and images') {
 					$tags[] = 'Sprites';
 					$tags[] = 'Removal';
-					$currentchangelogblock[] = array('type' => 'imagedel', 'body' => $item);
 				}
 				break;
 			case 'typo':
 			case 'spellcheck':
 				if($item != 'fixed a few typos') {
 					$tags[] = 'Grammar and Formatting';
-					$currentchangelogblock[] = array('type' => 'spellcheck', 'body' => $item);
 				}
 				break;
 			case 'balance':
 				if($item != 'rebalanced something'){
 					$tags[] = 'Balance';
-					$currentchangelogblock[] = array('type' => 'balance', 'body' => $item);
 				}
 				break;
 			case 'code_imp':
 			case 'code':
 				if($item != 'changed some code'){
 					$tags[] = 'Code Improvement';
-					$currentchangelogblock[] = array('type' => 'code_imp', 'body' => $item);
 				}
 				break;
 			case 'refactor':
 				if($item != 'refactored some code'){
 					$tags[] = 'Refactor';
-					$currentchangelogblock[] = array('type' => 'refactor', 'body' => $item);
 				}
 				break;
 			case 'config':
 				if($item != 'changed some config setting'){
 					$tags[] = 'Config Update';
-					$currentchangelogblock[] = array('type' => 'config', 'body' => $item);
 				}
 				break;
 			case 'admin':
 				if($item != 'messed with admin stuff'){
 					$tags[] = 'Administration';
-					$currentchangelogblock[] = array('type' => 'admin', 'body' => $item);
 				}
 				break;
-			case 'server':
-				if($item != 'something server ops should know')
-					$currentchangelogblock[] = array('type' => 'server', 'body' => $item);
-				break;
-			default:
-				//we add it to the last changelog entry as a separate line
-				if (count($currentchangelogblock) > 0)
-					$currentchangelogblock[count($currentchangelogblock)-1]['body'] .= "\n".$line;
-				break;
 		}
 	}
-
-	if(!count($changelogbody))
-		$no_changelog = true;
-
-	if ($no_changelog || !$compile)
-		return $tags;
-
-	$file = 'author: "'.trim(str_replace(array("\\", '"'), array("\\\\", "\\\""), $username)).'"'."\n";
-	$file .= "delete-after: True\n";
-	$file .= "changes: \n";
-	foreach ($changelogbody as $changelogitem) {
-		$type = $changelogitem['type'];
-		$body = trim(str_replace(array("\\", '"'), array("\\\\", "\\\""), $changelogitem['body']));
-		$file .= '  - '.$type.': "'.$body.'"';
-		$file .= "\n";
-	}
-	$content = array (
-		'branch' 	=> $payload['pull_request']['base']['ref'],
-		'message' 	=> 'Automatic changelog generation for PR #'.$payload['pull_request']['number'].' [ci skip]',
-		'content' 	=> base64_encode($file)
-	);
-
-	$filename = '/html/changelogs/AutoChangeLog-pr-'.$payload['pull_request']['number'].'.yml';
-	echo github_apisend($payload['pull_request']['base']['repo']['url'].'/contents'.$filename, 'PUT', $content);
 }
 
 function game_server_send($addr, $port, $str) {
diff --git a/tools/pull_request_hooks/autoChangelog.js b/tools/pull_request_hooks/autoChangelog.js
new file mode 100644
index 00000000000..bc24481f182
--- /dev/null
+++ b/tools/pull_request_hooks/autoChangelog.js
@@ -0,0 +1,42 @@
+import { parseChangelog } from "./changelogParser.js";
+
+const safeYml = (string) =>
+	string.replace(/\\/g, "\\\\").replace(/"/g, '\\"').replace(/\n/g, "\\n");
+
+export function changelogToYml(changelog, login) {
+	const author = changelog.author || login;
+	const ymlLines = [];
+
+	ymlLines.push(`author: "${safeYml(author)}"`);
+	ymlLines.push(`delete-after: True`);
+	ymlLines.push(`changes:`);
+
+	for (const change of changelog.changes) {
+		ymlLines.push(
+			`  - ${change.type.changelogKey}: "${safeYml(change.description)}"`
+		);
+	}
+
+	return ymlLines.join("\n");
+}
+
+export async function processAutoChangelog({ github, context }) {
+	const changelog = parseChangelog(context.payload.pull_request.body);
+	if (!changelog || changelog.changes.length === 0) {
+		console.log("no changelog found");
+		return;
+	}
+
+	const yml = changelogToYml(
+		changelog,
+		context.payload.pull_request.user.login
+	);
+
+	github.rest.repos.createOrUpdateFileContents({
+		owner: context.repo.owner,
+		repo: context.repo.repo,
+		path: `html/changelogs/AutoChangeLog-pr-${context.payload.pull_request.number}.yml`,
+		message: `Automatic changelog for PR #${context.payload.pull_request.number} [ci skip]`,
+		content: Buffer.from(yml).toString("base64"),
+	});
+}
diff --git a/tools/pull_request_hooks/autoChangelog.test.js b/tools/pull_request_hooks/autoChangelog.test.js
new file mode 100644
index 00000000000..e7c29c384a9
--- /dev/null
+++ b/tools/pull_request_hooks/autoChangelog.test.js
@@ -0,0 +1,21 @@
+import assert from "node:assert/strict";
+import { changelogToYml } from "./autoChangelog.js";
+import { parseChangelog } from "./changelogParser.js";
+
+assert.equal(
+	changelogToYml(
+		parseChangelog(`
+			My cool PR!
+			:cl: DenverCoder9
+			add: Adds new stuff
+			add: Adds more stuff
+			/:cl:
+		`)
+	),
+
+	`author: "DenverCoder9"
+delete-after: True
+changes:
+  - rscadd: "Adds new stuff"
+  - rscadd: "Adds more stuff"`
+);
diff --git a/tools/pull_request_hooks/changelogConfig.js b/tools/pull_request_hooks/changelogConfig.js
new file mode 100644
index 00000000000..a607fd9a457
--- /dev/null
+++ b/tools/pull_request_hooks/changelogConfig.js
@@ -0,0 +1,127 @@
+/**
+ * A map of changelog phrases to meta-information.
+ *
+ * The first entry in the list is used in the changelog YML file as the key when
+ * used, but other than that all entries are equivalent.
+ *
+ * placeholders - The default messages, if the changelog has this then we pretend it
+ * doesn't exist.
+ */
+export const CHANGELOG_ENTRIES = [
+	[
+		["rscadd", "add", "adds"],
+		{
+			placeholders: [
+				"Added new mechanics or gameplay changes",
+				"Added more things",
+			],
+		},
+	],
+
+	[
+		["bugfix", "fix", "fixes"],
+		{
+			placeholders: ["fixed a few things"],
+		},
+	],
+
+	[
+		["rscdel", "del", "dels"],
+		{
+			placeholders: ["Removed old things"],
+		},
+	],
+
+	[
+		["qol"],
+		{
+			placeholders: ["made something easier to use"],
+		},
+	],
+
+	[
+		["soundadd"],
+		{
+			placeholders: ["added a new sound thingy"],
+		},
+	],
+
+	[
+		["sounddel"],
+		{
+			placeholders: ["removed an old sound thingy"],
+		},
+	],
+
+	[
+		["imageadd"],
+		{
+			placeholders: ["added some icons and images"],
+		},
+	],
+
+	[
+		["imagedel"],
+		{
+			placeholders: ["deleted some icons and images"],
+		},
+	],
+
+	[
+		["spellcheck", "typo"],
+		{
+			placeholders: ["fixed a few typos"],
+		},
+	],
+
+	[
+		["balance"],
+		{
+			placeholders: ["rebalanced something"],
+		},
+	],
+
+	[
+		["code_imp", "code"],
+		{
+			placeholders: ["changed some code"],
+		},
+	],
+
+	[
+		["refactor"],
+		{
+			placeholders: ["refactored some code"],
+		},
+	],
+
+	[
+		["config"],
+		{
+			placeholders: ["changed some config setting"],
+		},
+	],
+
+	[
+		["admin"],
+		{
+			placeholders: ["messed with admin stuff"],
+		},
+	],
+
+	[
+		["server"],
+		{
+			placeholders: ["something server ops should know"],
+		},
+	],
+];
+
+// Valid changelog openers
+export const CHANGELOG_OPEN_TAGS = [":cl:", "??"];
+
+// Valid changelog closers
+export const CHANGELOG_CLOSE_TAGS = ["/:cl:", "/ :cl:", ":/cl:", "/??", "/ ??"];
+
+// Placeholder value for an author
+export const CHANGELOG_AUTHOR_PLACEHOLDER_NAME = "optional name here";
diff --git a/tools/pull_request_hooks/changelogParser.js b/tools/pull_request_hooks/changelogParser.js
new file mode 100644
index 00000000000..2daa2a57989
--- /dev/null
+++ b/tools/pull_request_hooks/changelogParser.js
@@ -0,0 +1,80 @@
+import * as changelogConfig from "./changelogConfig.js";
+
+const REGEX_CHANGELOG_LINE = /^(\w+): (.+)$/;
+
+const CHANGELOG_KEYS_TO_ENTRY = {};
+for (const [types, entry] of changelogConfig.CHANGELOG_ENTRIES) {
+	const entryWithChangelogKey = {
+		...entry,
+		changelogKey: types[0],
+	};
+
+	for (const type of types) {
+		CHANGELOG_KEYS_TO_ENTRY[type] = entryWithChangelogKey;
+	}
+}
+
+function parseChangelogBody(lines, openTag) {
+	const [changelogOpening] = lines.splice(0, 1);
+
+	const author =
+		changelogOpening.substring(openTag.length).trim() || undefined;
+
+	const changelog = {
+		author,
+		changes: [],
+	};
+
+	for (const line of lines) {
+		if (line.trim().length === 0) {
+			continue;
+		}
+
+		for (const closeTag of changelogConfig.CHANGELOG_CLOSE_TAGS) {
+			if (line.startsWith(closeTag)) {
+				return changelog;
+			}
+		}
+
+		const match = line.match(REGEX_CHANGELOG_LINE);
+		if (match) {
+			const [_, type, description] = match;
+
+			const entry = CHANGELOG_KEYS_TO_ENTRY[type];
+
+			if (entry.placeholders.includes(description)) {
+				continue;
+			}
+
+			if (entry) {
+				changelog.changes.push({
+					type: entry,
+					description,
+				});
+			}
+		} else {
+			const lastChange = changelog.changes[changelog.changes.length - 1];
+			if (lastChange) {
+				lastChange.description += `\n${line}`;
+			}
+		}
+	}
+
+	return changelog;
+}
+
+export function parseChangelog(text) {
+	const lines = text.split("\n").map((line) => line.trim());
+
+	for (let index = 0; index < lines.length; index++) {
+		const line = lines[index];
+
+		for (const openTag of changelogConfig.CHANGELOG_OPEN_TAGS) {
+			if (line.startsWith(openTag)) {
+				return parseChangelogBody(lines.slice(index), openTag);
+			}
+		}
+	}
+
+	return undefined;
+}
diff --git a/tools/pull_request_hooks/changelogParser.test.js b/tools/pull_request_hooks/changelogParser.test.js
new file mode 100644
index 00000000000..bcf044ee36d
--- /dev/null
+++ b/tools/pull_request_hooks/changelogParser.test.js
@@ -0,0 +1,72 @@
+import { strict as assert } from "node:assert";
+import { parseChangelog } from "./changelogParser.js";
+
+// Basic test
+const basicChangelog = parseChangelog(`
+	My cool PR!
+	:cl: DenverCoder9
+	add: Adds new stuff
+	/:cl:
+`);
+
+assert.equal(basicChangelog.author, "DenverCoder9");
+assert.equal(basicChangelog.changes.length, 1);
+assert.equal(basicChangelog.changes[0].type.changelogKey, "rscadd");
+assert.equal(basicChangelog.changes[0].description, "Adds new stuff");
+
+// Multi-line test
+const multiLineChangelog = parseChangelog(`
+	My cool PR!
+	:cl:
+	add: Adds new stuff
+	to the game
+	/:cl:
+`);
+
+assert.equal(multiLineChangelog.author, undefined);
+assert.equal(multiLineChangelog.changes.length, 1);
+assert.equal(multiLineChangelog.changes[0].type.changelogKey, "rscadd");
+assert.equal(
+	multiLineChangelog.changes[0].description,
+	"Adds new stuff\nto the game"
+);
+
+// Placeholders
+const placeholderChangelog = parseChangelog(`
+	My cool PR!
+	:cl:
+	add: Added new mechanics or gameplay changes
+	/:cl:
+`);
+
+assert.equal(placeholderChangelog.changes.length, 0);
+
+// No changelog
+const noChangelog = parseChangelog(`
+	My cool PR!
+`);
+
+assert.equal(noChangelog, undefined);
+
+// No /:cl:
+
+const noCloseChangelog = parseChangelog(`
+	My cool PR!
+	:cl:
+	add: Adds new stuff
+`);
+
+assert.equal(noCloseChangelog.changes.length, 1);
+assert.equal(noCloseChangelog.changes[0].type.changelogKey, "rscadd");
+assert.equal(noCloseChangelog.changes[0].description, "Adds new stuff");
+
+// :cl: with arbitrary text
+
+const arbitraryTextChangelog = parseChangelog(`
+	My cool PR!
+	:cl:
+	Adds new stuff
+	/:cl:
+`);
+
+assert.equal(arbitraryTextChangelog.changes.length, 0);
diff --git a/tools/pull_request_hooks/package.json b/tools/pull_request_hooks/package.json
new file mode 100644
index 00000000000..bedb411a912
--- /dev/null
+++ b/tools/pull_request_hooks/package.json
@@ -0,0 +1,3 @@
+{
+	"type": "module"
+}