diff --git a/packages/js/email-editor/src/blocks/core/rich-text.tsx b/packages/js/email-editor/src/blocks/core/rich-text.tsx
index 7b656f3da6..8e11e0745d 100644
--- a/packages/js/email-editor/src/blocks/core/rich-text.tsx
+++ b/packages/js/email-editor/src/blocks/core/rich-text.tsx
@@ -7,9 +7,14 @@ import {
 	createTextToHtmlMap,
 	getCursorPosition,
 	isMatchingComment,
+	replacePersonalizationTagsWithHTMLComments,
 } from '../../components/personalization-tags/rich-text-utils';
 import { PersonalizationTagsModal } from '../../components/personalization-tags/personalization-tags-modal';
 import { useCallback, useState } from '@wordpress/element';
+import { addFilter } from '@wordpress/hooks';
+import * as React from 'react';
+import { storeName } from '../../store';
+import { createHigherOrderComponent } from '@wordpress/compose';
 
 /**
  * Disable Rich text formats we currently cannot support
@@ -121,4 +126,82 @@ function extendRichTextFormats() {
 	} );
 }
 
-export { disableCertainRichTextFormats, extendRichTextFormats };
+const personalizationTagsLiveContentUpdate = createHigherOrderComponent(
+	( BlockEdit ) => ( props ) => {
+		const { attributes, setAttributes, name } = props;
+		const { content } = attributes;
+
+		// Fetch the personalization tags list
+		const list = useSelect(
+			( select ) => select( storeName ).getPersonalizationTagsList(),
+			[]
+		);
+
+		// Memoized function to replace content tags
+		const updatedContent = useCallback( () => {
+			if ( ! content ) {
+				return '';
+			}
+			return replacePersonalizationTagsWithHTMLComments( content, list );
+		}, [ content, list ] );
+
+		// Handle content updates
+		const handleSetAttributes = useCallback(
+			( newAttributes ) => {
+				if ( newAttributes.content !== undefined ) {
+					const replacedContent =
+						replacePersonalizationTagsWithHTMLComments(
+							newAttributes.content,
+							list
+						);
+					setAttributes( {
+						...newAttributes,
+						content: replacedContent,
+					} );
+				} else {
+					setAttributes( newAttributes );
+				}
+			},
+			[ list, setAttributes ]
+		);
+
+		// Only process supported blocks
+		if (
+			name === 'core/paragraph' ||
+			name === 'core/heading' ||
+			name === 'core/list-item'
+		) {
+			return (
+				<BlockEdit
+					{ ...props }
+					attributes={ {
+						...attributes,
+						content: updatedContent(),
+					} }
+					setAttributes={ handleSetAttributes }
+				/>
+			);
+		}
+
+		// Return default for unsupported blocks
+		return <BlockEdit { ...props } />;
+	},
+	'personalizationTagsLiveContentUpdate'
+);
+
+/**
+ * Replace written personalization tags with HTML comments in real-time.
+ */
+function replaceWrittenPersonalizationTags() {
+	addFilter(
+		'editor.BlockEdit',
+		'mailpoet-email-editor/with-live-content-update',
+		personalizationTagsLiveContentUpdate
+	);
+}
+
+export {
+	disableCertainRichTextFormats,
+	extendRichTextFormats,
+	replaceWrittenPersonalizationTags,
+};
diff --git a/packages/js/email-editor/src/blocks/index.ts b/packages/js/email-editor/src/blocks/index.ts
index 5093bd243a..4c6d71c20f 100644
--- a/packages/js/email-editor/src/blocks/index.ts
+++ b/packages/js/email-editor/src/blocks/index.ts
@@ -11,6 +11,7 @@ import { disableImageFilter, hideExpandOnClick } from './core/image';
 import {
 	disableCertainRichTextFormats,
 	extendRichTextFormats,
+	replaceWrittenPersonalizationTags,
 } from './core/rich-text';
 import { enhanceButtonBlock } from './core/button';
 import { enhanceButtonsBlock } from './core/buttons';
@@ -29,6 +30,7 @@ export function initBlocks() {
 	enhanceColumnsBlock();
 	enhancePostContentBlock();
 	extendRichTextFormats();
+	replaceWrittenPersonalizationTags();
 	alterSupportConfiguration();
 	registerCoreBlocks();
 }
diff --git a/packages/js/email-editor/src/components/personalization-tags/rich-text-utils.ts b/packages/js/email-editor/src/components/personalization-tags/rich-text-utils.ts
index b3b4d660f3..5b72d26ee9 100644
--- a/packages/js/email-editor/src/components/personalization-tags/rich-text-utils.ts
+++ b/packages/js/email-editor/src/components/personalization-tags/rich-text-utils.ts
@@ -1,4 +1,5 @@
 import * as React from '@wordpress/element';
+import { PersonalizationTag } from '../../store';
 
 /**
  * Maps indices of characters in HTML representation of the value to corresponding characters of stored value in RichText content. The stored value doesn't contain tags.
@@ -184,9 +185,35 @@ const isMatchingComment = (
 	return htmlCommentRegex.test( substring );
 };
 
+/**
+ * Replace registered personalization tags with HTML comments in content.
+ * @param content string The content to replace the tags in.
+ * @param tags    PersonalizationTag[] The tags to replace in the content.
+ */
+const replacePersonalizationTagsWithHTMLComments = (
+	content: string,
+	tags: PersonalizationTag[]
+) => {
+	tags.forEach( ( tag ) => {
+		if ( ! content.includes( tag.token ) ) {
+			// Skip if the token is not in the content
+			return;
+		}
+
+		const escapedRegExp = tag.token.replace(
+			/[.*+?^${}()|[\]\\]/g,
+			'\\$&'
+		); // Escape special characters
+		const regex = new RegExp( `(?<!<!--)${ escapedRegExp }(?!-->)`, 'g' ); // Match token not inside HTML comments
+		content = content.replace( regex, `<!--${ tag.token }-->` );
+	} );
+	return content;
+};
+
 export {
 	isMatchingComment,
 	getCursorPosition,
 	createTextToHtmlMap,
 	mapRichTextToValue,
+	replacePersonalizationTagsWithHTMLComments,
 };