diff --git a/src/wp-admin/includes/misc.php b/src/wp-admin/includes/misc.php
index 2a07061796..13552d56cf 100644
--- a/src/wp-admin/includes/misc.php
+++ b/src/wp-admin/includes/misc.php
@@ -39,11 +39,12 @@ function got_mod_rewrite() {
  * @since 3.7.0
  *
  * @global bool $is_nginx
+ * @global bool $is_caddy
  *
  * @return bool Whether the server supports URL rewriting.
  */
 function got_url_rewrite() {
-	$got_url_rewrite = ( got_mod_rewrite() || $GLOBALS['is_nginx'] || iis7_supports_permalinks() );
+	$got_url_rewrite = ( got_mod_rewrite() || $GLOBALS['is_nginx'] || $GLOBALS['is_caddy'] || iis7_supports_permalinks() );
 
 	/**
 	 * Filters whether URL rewriting is available.
diff --git a/src/wp-admin/options-permalink.php b/src/wp-admin/options-permalink.php
index 379dc8a0f5..46da9be8f3 100644
--- a/src/wp-admin/options-permalink.php
+++ b/src/wp-admin/options-permalink.php
@@ -154,7 +154,7 @@ if ( $iis7_permalinks ) {
 	} else {
 		$writable = false;
 	}
-} elseif ( $is_nginx ) {
+} elseif ( $is_nginx || $is_caddy ) {
 	$writable = false;
 } else {
 	if ( ( ! file_exists( $home_path . '.htaccess' )
@@ -190,7 +190,7 @@ if ( $structure_updated ) {
 					'<code>web.config</code>'
 				);
 			}
-		} elseif ( ! $is_nginx && $htaccess_update_required && ! $writable ) {
+		} elseif ( ! $is_nginx && ! $is_caddy && $htaccess_update_required && ! $writable ) {
 			$message = sprintf(
 				/* translators: %s: .htaccess */
 				__( 'You should update your %s file now.' ),
diff --git a/src/wp-includes/vars.php b/src/wp-includes/vars.php
index dc28b8509a..05df7ec99a 100644
--- a/src/wp-includes/vars.php
+++ b/src/wp-includes/vars.php
@@ -17,7 +17,7 @@
 
 global $pagenow,
 	$is_lynx, $is_gecko, $is_winIE, $is_macIE, $is_opera, $is_NS4, $is_safari, $is_chrome, $is_iphone, $is_IE, $is_edge,
-	$is_apache, $is_IIS, $is_iis7, $is_nginx;
+	$is_apache, $is_IIS, $is_iis7, $is_nginx, $is_caddy;
 
 // On which page are we?
 if ( is_admin() ) {
@@ -126,6 +126,13 @@ $is_apache = ( str_contains( $_SERVER['SERVER_SOFTWARE'], 'Apache' ) || str_cont
  */
 $is_nginx = ( str_contains( $_SERVER['SERVER_SOFTWARE'], 'nginx' ) );
 
+/**
+ * Whether the server software is Caddy or something else
+ *
+ * @global bool $is_caddy
+ */
+$is_caddy = ( str_contains( $_SERVER['SERVER_SOFTWARE'], 'Caddy' ) );
+
 /**
  * Whether the server software is IIS or something else
  *