diff --git a/NEWS b/NEWS
index 474db936ef15..62353d3107b2 100644
--- a/NEWS
+++ b/NEWS
@@ -21,6 +21,8 @@ PHP                                                                        NEWS
 - Opcache:
   . Fixed bug GH-22857 (Function JIT emits wrong code for FETCH_OBJ_FUNC_ARG on a
     property hook getter, losing register-held variables). (Zhao Hao)
+  . Fixed crash in observer API calling cases() on an enum preloaded with
+    opcache_compile_file(). (Thomas Atkinson)
 
 - OpenSSL:
   . Fix missing error check on invalid alpn protocols. (ndossche)
diff --git a/Zend/zend_enum.c b/Zend/zend_enum.c
index 464e7d801a89..e1190d4e3289 100644
--- a/Zend/zend_enum.c
+++ b/Zend/zend_enum.c
@@ -418,10 +418,10 @@ static void zend_enum_register_func(zend_class_entry *ce, zend_known_string_id n
 	zif->module = EG(current_module);
 	zif->scope = ce;
 	zif->T = ZEND_OBSERVER_ENABLED;
+	if (CG(compiler_options) & ZEND_COMPILE_PRELOAD) {
+		zif->fn_flags |= ZEND_ACC_PRELOADED;
+	}
 	if (EG(active)) { // at run-time
-		if (CG(compiler_options) & ZEND_COMPILE_PRELOAD) {
-			zif->fn_flags |= ZEND_ACC_PRELOADED;
-		}
 		ZEND_MAP_PTR_INIT(zif->run_time_cache, zend_arena_calloc(&CG(arena), 1, zend_internal_run_time_cache_reserved_size()));
 	} else {
 #ifdef ZTS
diff --git a/ext/opcache/tests/preload_enum_compile_only.inc b/ext/opcache/tests/preload_enum_compile_only.inc
new file mode 100644
index 000000000000..fd7eeddd932e
--- /dev/null
+++ b/ext/opcache/tests/preload_enum_compile_only.inc
@@ -0,0 +1,3 @@
+<?php
+
+opcache_compile_file(__DIR__ . '/preload_enum.inc');
diff --git a/ext/opcache/tests/preload_enum_observed_compile_only.phpt b/ext/opcache/tests/preload_enum_observed_compile_only.phpt
new file mode 100644
index 000000000000..d2b7582e9683
--- /dev/null
+++ b/ext/opcache/tests/preload_enum_observed_compile_only.phpt
@@ -0,0 +1,30 @@
+--TEST--
+Crash in observer API calling cases() on a compile-only preloaded enum
+--EXTENSIONS--
+opcache
+zend_test
+--INI--
+opcache.enable=1
+opcache.enable_cli=1
+opcache.optimization_level=-1
+opcache.preload={PWD}/preload_enum_compile_only.inc
+zend_test.observer.enabled=1
+zend_test.observer.observe_all=1
+zend_test.observer.show_output=0
+--SKIPIF--
+<?php
+if (PHP_OS_FAMILY == 'Windows') die('skip Preloading is not supported on Windows');
+?>
+--FILE--
+<?php
+
+var_dump(MyEnum::cases());
+
+?>
+--EXPECT--
+array(2) {
+  [0]=>
+  enum(MyEnum::Foo)
+  [1]=>
+  enum(MyEnum::Bar)
+}