diff --git a/Sources/Autolinker.php b/Sources/Autolinker.php
index 6d3b370a2b..3208667b54 100644
--- a/Sources/Autolinker.php
+++ b/Sources/Autolinker.php
@@ -217,6 +217,13 @@ class Autolinker
 	 */
 	protected string $js_email_regex;
 
+	/**
+	 * @var string
+	 *
+	 * Regular expression to match the named entities in HTML5.
+	 */
+	protected string $entities_regex;
+
 	/****************************
 	 * Internal static properties
 	 ****************************/
@@ -377,10 +384,9 @@ public function detectUrls(string $string, bool $plaintext_only = false): array
 	{
 		static $no_autolink_regex;
 
-		// An   right after a URL can break the autolinker
-		if (str_contains($string, ' ')) {
-			$string = strtr($string, [' ' => str_repeat(html_entity_decode(' ', 0, $this->encoding), 3)]);
-		}
+		// An entity right after the URL can break the autolinker.
+		$this->setEntitiesRegex();
+		$string = preg_replace('~(' . $this->entities_regex . ')*(?=\s|$)~u', ' ', $string);
 
 		$this->setUrlRegex();
 
@@ -467,10 +473,9 @@ public function detectUrls(string $string, bool $plaintext_only = false): array
 	 */
 	public function detectEmails(string $string, bool $plaintext_only = false): array
 	{
-		// An   right after a email address can break the autolinker
-		if (str_contains($string, ' ')) {
-			$string = strtr($string, [' ' => str_repeat(html_entity_decode(' ', 0, $this->encoding), 3)]);
-		}
+		// An entity right after the email address can break the autolinker.
+		$this->setEntitiesRegex();
+		$string = preg_replace('~(' . $this->entities_regex . ')*(?=\s|$)~u', ' ', $string);
 
 		$this->setEmailRegex();
 
@@ -758,10 +763,63 @@ public static function load(bool $only_basic = false): object
 		return self::$instance;
 	}
 
+	/**
+	 * Creates the JavaScript file used for autolinking in the editor.
+	 *
+	 * @param bool $force Whether to overwrite an existing file. Default: false.
+	 */
+	public static function createJavaScriptFile(bool $force = false): void
+	{
+		if (empty(Config::$modSettings['autoLinkUrls'])) {
+			return;
+		}
+
+		if (!isset(Theme::$current)) {
+			Theme::loadEssential();
+		}
+
+		if (!$force && file_exists(Theme::$current->settings['default_theme_dir'] . '/scripts/autolinker.js')) {
+			return;
+		}
+
+		$js[] = 'const autolinker_regexes = new Map();';
+
+		$regexes = self::load()->getJavaScriptUrlRegexes();
+		$regexes['email'] = self::load()->getJavaScriptEmailRegex();
+
+		foreach ($regexes as $key => $value) {
+			$js[] = 'autolinker_regexes.set(' . Utils::escapeJavaScript($key) . ', new RegExp(' . Utils::escapeJavaScript($value) . ', "giu"));';
+
+			$js[] = 'autolinker_regexes.set(' . Utils::escapeJavaScript('paste_' . $key) . ', new RegExp(' . Utils::escapeJavaScript('(?<=^|\s|<br>)' . $value . '(?=$|\s|<br>|[' . self::$excluded_trailing_chars . '])') . ', "giu"));';
+
+			$js[] = 'autolinker_regexes.set(' . Utils::escapeJavaScript('keypress_' . $key) . ', new RegExp(' . Utils::escapeJavaScript($value . '(?=[' . self::$excluded_trailing_chars . preg_quote(implode(array_merge(array_keys(self::$balanced_pairs), self::$balanced_pairs)), '/') . ']*\s$)') . ', "giu"));';
+		}
+
+		$js[] = 'const autolinker_balanced_pairs = new Map();';
+
+		foreach (self::$balanced_pairs as $opener => $closer) {
+			$js[] = 'autolinker_balanced_pairs.set(' . Utils::escapeJavaScript($opener) . ', ' . Utils::escapeJavaScript($closer) . ');';
+		}
+
+		file_put_contents(Theme::$current->settings['default_theme_dir'] . '/scripts/autolinker.js', implode("\n", $js));
+	}
+
 	/*******************
 	 * Internal methods.
 	 *******************/
 
+	/**
+	 * Sets $this->entities_regex.
+	 */
+	protected function setEntitiesRegex(): void
+	{
+		if (isset($this->entities_regex)) {
+			return;
+		}
+
+		$this->entities_regex = '(?' . '>&(?' . '>' . Utils::buildRegex(array_map(fn ($ent) => ltrim($ent, '&'), get_html_translation_table(HTML_ENTITIES, ENT_HTML5 | ENT_QUOTES)), '~') . '|(?' . '>#(?' . '>x[0-9a-fA-F]{1,6}|\d{1,7});)))';
+	}
+
 	/**
 	 * Sets $this->tld_regex.
 	 */
diff --git a/Sources/Editor.php b/Sources/Editor.php
index d4d4274b14..7266e9b2f7 100644
--- a/Sources/Editor.php
+++ b/Sources/Editor.php
@@ -227,7 +227,7 @@ public function __construct(array $options)
 		$this->columns = (int) ($options['columns'] ?? 60);
 		$this->rows = (int) ($options['rows'] ?? 18);
 		$this->width = (string) ($options['width'] ?? '70%');
-		$this->height = (string) ($options['height'] ?? '175px');
+		$this->height = (string) ($options['height'] ?? '250px');
 		$this->form = (string) ($options['form'] ?? 'postmodify');
 		$this->preview_type = (int) ($options['preview_type'] ?? self::PREVIEW_HTML);
 		$this->labels = (array) ($options['labels'] ?? []);
@@ -775,34 +775,19 @@ protected function setSCEditorOptions(): void
 		// Set up the SCEditor options
 		$this->sce_options = [
 			'width' => $this->width ?? '100%',
-			'height' => $this->height ?? '175px',
+			'height' => $this->height ?? '250px',
 			'style' => Theme::$current->settings[file_exists(Theme::$current->settings['theme_dir'] . '/css/jquery.sceditor.default.css') ? 'theme_url' : 'default_theme_url'] . '/css/jquery.sceditor.default.css' . Utils::$context['browser_cache'],
 			'emoticonsCompat' => true,
 			'colors' => 'black,maroon,brown,green,navy,grey,red,orange,teal,blue,white,hotpink,yellow,limegreen,purple',
 			'format' => 'bbcode',
-			'plugins' => !empty(Config::$modSettings['autoLinkUrls']) ? 'autolinker' : '',
+			'plugins' => '',
 			'bbcodeTrim' => false,
 		];
 
 		if (!empty(Config::$modSettings['autoLinkUrls'])) {
-			$js = "\n\t\t" . 'const autolinker_regexes = new Map();';
-
-			$regexes = Autolinker::load()->getJavaScriptUrlRegexes();
-			$regexes['email'] = Autolinker::load()->getJavaScriptEmailRegex();
-
-			foreach ($regexes as $key => $value) {
-				$js .= "\n\t\t" . 'autolinker_regexes.set(' . Utils::escapeJavaScript($key) . ', new RegExp(' . Utils::escapeJavaScript($value) . ', "giu"));';
-				$js .= "\n\t\t" . 'autolinker_regexes.set(' . Utils::escapeJavaScript('paste_' . $key) . ', new RegExp(' . Utils::escapeJavaScript('(?<=^|\s|<br>)' . $value . '(?=$|\s|<br>|[' . Autolinker::$excluded_trailing_chars . '])') . ', "giu"));';
-				$js .= "\n\t\t" . 'autolinker_regexes.set(' . Utils::escapeJavaScript('keypress_' . $key) . ', new RegExp(' . Utils::escapeJavaScript($value . '(?=[' . Autolinker::$excluded_trailing_chars . preg_quote(implode(array_merge(array_keys(Autolinker::$balanced_pairs), Autolinker::$balanced_pairs)), '/') . ']*\s$)') . ', "giu"));';
-			}
-
-			$js .= "\n\t\t" . 'const autolinker_balanced_pairs = new Map();';
-
-			foreach (Autolinker::$balanced_pairs as $opener => $closer) {
-				$js .= "\n\t\t" . 'autolinker_balanced_pairs.set(' . Utils::escapeJavaScript($opener) . ', ' . Utils::escapeJavaScript($closer) . ');';
-			}
-
-			Theme::addInlineJavaScript($js);
+			$this->sce_options['plugins'] = 'autolinker';
+			Autolinker::createJavaScriptFile();
+			Theme::loadJavaScriptFile('autolinker.js', ['minimize' => true], 'smf_autolinker');
 		}
 
 		if (!empty($this->locale)) {
diff --git a/Sources/Url.php b/Sources/Url.php
index 32432b4e03..c06e8c3cec 100644
--- a/Sources/Url.php
+++ b/Sources/Url.php
@@ -753,6 +753,11 @@ function ($line) {
 		// Remember the new regex in Config::$modSettings
 		Config::updateModSettings(['tld_regex' => $tld_regex]);
 
+		// Update the editor's autolinker JavaScript.
+		if ($update) {
+			Autolinker::createJavaScriptFile(true);
+		}
+
 		// Redundant repetition is redundant
 		$done = true;
 	}