diff --git a/src/filters.php b/src/filters.php
index e06e954..9250554 100644
--- a/src/filters.php
+++ b/src/filters.php
@@ -55,7 +55,7 @@ function s3_multisite_upload_dir( $upload ) {
 // Conditionally adds a filter only during the upload process, this filter adds a second filter that removes all the image sizes.
 // It also adds a filter to preemptively add the sizes to the attachment metadata, otherwise the first filter would prevent the sizes from being added.
 add_filter(
-	'wp_handle_upload_prefilter',
+	'wp_handle_upload',
 	function( $file ) {
 		// This filters the image sizes that are generated during the upload process, removing all of them by returning an empty array.
 		add_filter(
@@ -140,3 +140,19 @@ function( $old_site ) {
 	10,
 	2
 );
+
+/**
+ * Add a filter to the wp_handle_replace event, declared by the enable-media-replace plugin.
+ * The filter passes the post ID of the file being replaced, and we use this to delete the old rendered media library files.
+ * Otherwise, the old scaled versions of the file won't be replaced with updated versions.
+ */
+add_filter(
+	'wp_handle_replace',
+	function( $post_details ) {
+		// Get the file path from the attachment ID.
+		$file = get_attached_file( $post_details['post_id'] );
+
+		// Delete the old rendered media library files for the file being replaced.
+		delete_scaled_for_s3_key( $file );
+	}
+);
diff --git a/src/s3-assets.php b/src/s3-assets.php
index 2704685..96babf7 100644
--- a/src/s3-assets.php
+++ b/src/s3-assets.php
@@ -123,3 +123,66 @@ function s3_object_exists( $key ) {
 
 	return $result;
 }
+
+/**
+ * Delete the rendered media library files from S3 for a given key.
+ *
+ * Takes a full s3:// path, extracts the path fragment from the key, and deletes all of the rendered media library files for that path fragment.
+ * The path fragment is everything after bucket name and 'original_media', like 'www.bu.edu/path/image.png'.
+ * Everything in the /rendered_media/ directory that matches 'www.bu.edu/path/image' will be deleted.
+ *
+ * @since 1.0.1
+ *
+ * @param string $s3_key The key of the object to delete.
+ *
+ * @return bool True if successful, false if not.
+ */
+function delete_scaled_for_s3_key( $s3_key ) {
+	// Extract everything after the occurence of the S3_UPLOADS_BUCKET constant (which includes the 'original_media').
+	$partial_path = substr( $s3_key, strpos( $s3_key, S3_UPLOADS_BUCKET ) + strlen( S3_UPLOADS_BUCKET ) );
+	// Strip the leading slash if it exists.
+	$partial_path = ltrim( $partial_path, '/' );
+
+	// Calculate the path fragment to use as the matching key fragment for the s3 deleteMatchingObjects method.
+	$filename_root = pathinfo( $partial_path, PATHINFO_FILENAME );
+	$path_fragment = dirname( $partial_path ) . '/' . $filename_root;
+
+	// Delete all of the rendered media library files.
+	return delete_scaled_for_original( $path_fragment );
+}
+
+/**
+ * Delete the rendered media library files from S3 for a given original path fragment.
+ *
+ * Deletes all of the rendered media library files from S3 for a given original path fragment.
+ * The path fragment is everything after bucket name and 'original_media', which will be
+ * the web url without the https:// protocol, like 'www.bu.edu/path/image.png'. This will delete any
+ * sized files like 'www.bu.edu/path/image-300x300.png'.
+ *
+ * @since 1.0.1
+ *
+ * @param string $path_fragment The path fragment to delete, like www.bu.edu/path/image.png.
+ *
+ * @return bool True if successful, false if not.
+ */
+function delete_scaled_for_original( $path_fragment ) {
+	// Create the S3 client, and get the bucket name and site key.
+	$s3_client = new_s3_client();
+	$bucket    = str_replace( '/original_media', '', S3_UPLOADS_BUCKET );
+
+	// Delete all of the rendered media library files.
+	try {
+		// Delete all of the rendered media library files.
+		$s3_client->deleteMatchingObjects( $bucket, "rendered_media/{$path_fragment}" );
+
+	} catch ( AwsException $e ) {
+		// Handle the exception.
+		// phpcs:ignore WordPress.PHP.DevelopmentFunctions.error_log_error_log
+		error_log( $e->getMessage() );
+		// Return false if unsuccessful.
+		return false;
+	}
+
+	// Return true if successful.
+	return true;
+}