diff --git a/module/tweaks/chatImageLinks.mjs b/module/tweaks/chatImageLinks.mjs
index 1e6f708..b75ad9c 100644
--- a/module/tweaks/chatImageLinks.mjs
+++ b/module/tweaks/chatImageLinks.mjs
@@ -3,8 +3,6 @@ import { __ID__ } from "../consts.mjs";
 import { Logger } from "../utils/Logger.mjs";
 import { preventTweakRegistration } from "../utils/preRegisterTweak.mjs";
 
-// const { DialogV2 } = foundry.applications.api;
-
 const key = `chatImageLinks`;
 const IMAGE_TYPES = [
 	`png`,
@@ -18,6 +16,9 @@ export function chatImageLinks() {
 	status[key] = SettingStatusEnum.Unknown;
 	if (preventTweakRegistration(key)) { return };
 
+	/** @type {number|null} */
+	let hookID = null;
+
 	// #region Registration
 	Logger.log(`Registering setting: ${key}`);
 	game.settings.register(__ID__, key, {
@@ -28,6 +29,13 @@ export function chatImageLinks() {
 		default: true,
 		config: true,
 		requiresReload: true,
+		onChange: (newValue) => {
+			if (newValue) {
+				hookID = Hooks.on(`chatMessage`, chatMessageHandler);
+			} else if (hookID != null) {
+				Hooks.off(`chatMessage`, hookID);
+			};
+		},
 	});
 
 	game.settings.register(__ID__, key + `-showPromptAgain`, {
@@ -40,76 +48,71 @@ export function chatImageLinks() {
 
 	// #region Implementation
 	if (game.settings.get(__ID__, key)) {
-		Logger.log(`setting:${key} | Adding text enricher`);
-
-		// MARK: Enricher
-		const pattern = new RegExp(
-			`(?<!=|")(image:\\/\\/.*\\.(?:${IMAGE_TYPES.join(`|`)}))`,
-			`gi`,
-		);
-
-		CONFIG.TextEditor.enrichers.push({
-			pattern,
-			replaceParent: true,
-			enricher: async (url) => {
-				Logger.debug(url);
-				url = url[0].replace(/^image:\/\//, ``);
-				const secure = `https://${url}`;
-				const insecure = `http://${url}`;
-
-				if (await isAcceptableImage(secure)) {
-					const img = document.createElement(`img`);
-					img.src = secure;
-					img.alt = secure;
-					return img;
-				};
-
-				if (await isAcceptableImage(insecure)) {
-					const img = document.createElement(`img`);
-					img.src = insecure;
-					img.alt = insecure;
-					return img;
-				};
-
-				return null;
-			},
-		});
-
-		// MARK: Chat Input
-		// Hooks.on(`chatMessage`, (chatLog, message, options) => {
-		// 	if (!game.settings.get(__ID__, key)) { return };
-
-		// 	const match = message.match(pattern);
-		// 	if (!match) { return };
-
-		// 	DialogV2.wait({
-		// 		rejectClose: false,
-		// 		content: game.i18n.localize(`OFT.dialogs.chatImageLinks.didYouKnowImageLink`),
-		// 		buttons: [
-		// 			{ action: ``, label: `OFT.dialogs.chatImageLinks.convertAndDontShowAgain` },
-		// 			{ action: ``, label: `OFT.dialogs.chatImageLinks.justConvert` },
-		// 			{ action: ``, label: `OFT.dialogs.chatImageLinks.ignoreAndDontShowAgain` },
-		// 			{ action: ``, label: `OFT.dialogs.chatImageLinks.disableEntirely` },
-		// 		],
-		// 	})
-		// 		.then((selected) => {
-		// 			chatLog.processMessage(message, options);
-		// 		});
-
-		// 	return false;
-		// });
-	}
+		Logger.log(`setting:${key} | Adding chat message listener`);
+		Hooks.on(`chatMessage`, chatMessageHandler);
+	};
 	// #endregion Implementation
 
 	status[key] = SettingStatusEnum.Registered;
 };
 
 // #region Helpers
+const pattern = new RegExp(
+	`https?:\\/\\/\\S*\\.(?:${IMAGE_TYPES.join(`|`)})`,
+	`gi`,
+);
+
+// MARK: Mutate & Resend
+const handled = new Set();
+async function mutateAndResendMessage(chatLog, message, options) {
+	const match = message.match(pattern);
+	if (!match) { return };
+
+	const validMatches = new Set();
+
+	const matches = message.match(pattern);
+	for (const match of matches) {
+		if (await isAcceptableImage(match)) {
+			validMatches.add(match);
+		};
+	};
+
+	message = message.replaceAll(
+		pattern,
+		(url) => {
+			if (!validMatches.has(url)) {
+				return url;
+			};
+			return `<img src="${url}" alt="${url}">`;
+		},
+	);
+
+	handled.add(message);
+	chatLog.processMessage(message, options);
+};
+
+// MARK: Chat Message
+/**
+ * Must be synchronous since it is a hook handler, but the mutation +
+ * resending can be done asynchronously since it doesn't matter how
+ * long it takes.
+ */
+function chatMessageHandler(chatLog, message, options) {
+	if (!game.settings.get(__ID__, key)) { return };
+	if (handled.has(message)) { return };
+	mutateAndResendMessage(chatLog, message, options);
+	return false;
+};
+
+// MARK: isAcceptableImage
 async function isAcceptableImage(url) {
+	if (!URL.canParse(url)) { return false };
+
 	try {
 		const response = await fetch(url, { method: `HEAD` });
 		const contentType = response.headers.get(`Content-Type`);
 		Logger.debug(`Image data:`, { url, contentType });
+
 		let [ superType, subtype ] = contentType.split(`/`);
 		if (superType !== `image`) {
 			return false;