diff --git a/ext/reflection/tests/ReflectionExtension_getClassNames_basic.phpt b/ext/reflection/tests/ReflectionExtension_getClassNames_basic.phpt
index 4f1da6fc6677e..f5697e0bc667d 100644
--- a/ext/reflection/tests/ReflectionExtension_getClassNames_basic.phpt
+++ b/ext/reflection/tests/ReflectionExtension_getClassNames_basic.phpt
@@ -8,7 +8,7 @@ $standard = new ReflectionExtension('standard');
 var_dump($standard->getClassNames());
 ?>
 --EXPECT--
-array(9) {
+array(11) {
   [0]=>
   string(22) "__PHP_Incomplete_Class"
   [1]=>
@@ -18,13 +18,17 @@ array(9) {
   [3]=>
   string(15) "FileSystemError"
   [4]=>
-  string(23) "InsufficientPermissions"
+  string(12) "FileNotFound"
   [5]=>
-  string(16) "TemporaryFailure"
+  string(12) "NotDirectory"
   [6]=>
-  string(15) "php_user_filter"
+  string(23) "InsufficientPermissions"
   [7]=>
-  string(9) "Directory"
+  string(16) "TemporaryFailure"
   [8]=>
+  string(15) "php_user_filter"
+  [9]=>
+  string(9) "Directory"
+  [10]=>
   string(14) "AssertionError"
 }
diff --git a/ext/standard/dir.c b/ext/standard/dir.c
index 69c9de886d7da..fbef40f60ce66 100644
--- a/ext/standard/dir.c
+++ b/ext/standard/dir.c
@@ -279,7 +279,7 @@ PHP_FUNCTION(chroot)
 
 	ret = chroot(str);
 	if (ret != 0) {
-		php_exception_or_warning_docref(NULL, zend_ce_filesystem_error, "%s (errno %d)", strerror(errno), errno);
+		handle_io_error(errno, str);
 		RETURN_FALSE;
 	}
 
diff --git a/ext/standard/io_exceptions.c b/ext/standard/io_exceptions.c
index a86e9b4cbe5b7..1a4e5f70e0c53 100644
--- a/ext/standard/io_exceptions.c
+++ b/ext/standard/io_exceptions.c
@@ -24,6 +24,8 @@
 PHPAPI zend_class_entry *zend_ce_filesystem;
 PHPAPI zend_class_entry *zend_ce_network;
 PHPAPI zend_class_entry *zend_ce_filesystem_error;
+PHPAPI zend_class_entry *zend_ce_file_not_found;
+PHPAPI zend_class_entry *zend_ce_not_directory;
 PHPAPI zend_class_entry *zend_ce_insufficient_permissions;
 PHPAPI zend_class_entry *zend_ce_temporary_failure;
 
@@ -42,6 +44,14 @@ PHP_MINIT_FUNCTION(io_exceptions) {
 	zend_ce_filesystem_error = zend_register_internal_class_ex(&ce, zend_ce_exception);
 	zend_class_implements(zend_ce_filesystem_error, 1, zend_ce_filesystem);
 
+	INIT_CLASS_ENTRY(ce, "FileNotFound", class_FileNotFound_methods);
+	zend_ce_file_not_found = zend_register_internal_class_ex(&ce, zend_ce_exception);
+	zend_class_implements(zend_ce_file_not_found, 1, zend_ce_filesystem);
+
+	INIT_CLASS_ENTRY(ce, "NotDirectory", class_FileNotFound_methods);
+	zend_ce_not_directory = zend_register_internal_class_ex(&ce, zend_ce_exception);
+	zend_class_implements(zend_ce_not_directory, 1, zend_ce_filesystem);
+
 	INIT_CLASS_ENTRY(ce, "InsufficientPermissions", class_InsufficientPermissions_methods);
 	zend_ce_insufficient_permissions = zend_register_internal_class_ex(&ce, zend_ce_exception);
 	zend_class_implements(zend_ce_insufficient_permissions, 1, zend_ce_filesystem);
@@ -52,3 +62,20 @@ PHP_MINIT_FUNCTION(io_exceptions) {
 
 	return SUCCESS;
 }
+
+PHPAPI void handle_io_error(int error, const char *path) {
+	if (path == NULL) {
+		path = "[unknown]";
+	}
+	switch (error) {
+		case ENOENT:
+            php_exception_or_warning_docref(NULL, zend_ce_file_not_found, "File not found: \"%s\"", path);
+		    break;
+		case ENOTDIR:
+            php_exception_or_warning_docref(NULL, zend_ce_not_directory, "\"%s\" is not a directory", path);
+		    break;
+		default:
+            php_exception_or_warning_docref(NULL, zend_ce_filesystem_error, "%s (path: \"%s\", errno %d)", strerror(errno), path, errno);
+			break;
+	}
+}
diff --git a/ext/standard/io_exceptions.h b/ext/standard/io_exceptions.h
index ab653b2253277..1f4c36b8400b7 100644
--- a/ext/standard/io_exceptions.h
+++ b/ext/standard/io_exceptions.h
@@ -24,9 +24,13 @@ BEGIN_EXTERN_C()
 extern PHPAPI zend_class_entry *zend_ce_filesystem;
 extern PHPAPI zend_class_entry *zend_ce_network;
 extern PHPAPI zend_class_entry *zend_ce_filesystem_error;
+extern PHPAPI zend_class_entry *zend_ce_file_not_found;
+extern PHPAPI zend_class_entry *zend_ce_not_directory;
 extern PHPAPI zend_class_entry *zend_ce_insufficient_permissions;
 extern PHPAPI zend_class_entry *zend_ce_temporary_failure;
 
 END_EXTERN_C()
 
+PHPAPI void handle_io_error(int error, const char *path);
+
 #endif /* PHP_IO_EXCEPTION */
diff --git a/ext/standard/io_exceptions.stub.php b/ext/standard/io_exceptions.stub.php
index 8e93b24c66af9..06dae6d317e14 100644
--- a/ext/standard/io_exceptions.stub.php
+++ b/ext/standard/io_exceptions.stub.php
@@ -9,6 +9,10 @@ interface Network extends IO {}
 /* Should use more specialized ones instead but for PoC will use this instead */
 class FileSystemError extends Exception implements FileSystem {}
 
+class FileNotFound extends Exception implements FileSystem {}
+
+class NotDirectory extends Exception implements FileSystem {}
+
 class InsufficientPermissions extends Exception implements FileSystem {}
 
 class TemporaryFailure extends Exception implements Network {}
diff --git a/ext/standard/io_exceptions_arginfo.h b/ext/standard/io_exceptions_arginfo.h
index afc77e11761e5..2b8acb4bdbebf 100644
--- a/ext/standard/io_exceptions_arginfo.h
+++ b/ext/standard/io_exceptions_arginfo.h
@@ -1,5 +1,5 @@
 /* This is a generated file, edit the .stub.php file instead.
- * Stub hash: 68880a94d8393c0d367cee9e9c18c8ac6d16d9f2 */
+ * Stub hash: c4ecc9d6fb58a424dc63d5c5a039843b89273142 */
 
 
 
@@ -19,6 +19,16 @@ static const zend_function_entry class_FileSystemError_methods[] = {
 };
 
 
+static const zend_function_entry class_FileNotFound_methods[] = {
+	ZEND_FE_END
+};
+
+
+static const zend_function_entry class_NotDirectory_methods[] = {
+	ZEND_FE_END
+};
+
+
 static const zend_function_entry class_InsufficientPermissions_methods[] = {
 	ZEND_FE_END
 };
diff --git a/ext/standard/tests/dir/chroot_throw_on_error.phpt b/ext/standard/tests/dir/chroot_throw_on_error.phpt
new file mode 100644
index 0000000000000..27b8ac373c590
--- /dev/null
+++ b/ext/standard/tests/dir/chroot_throw_on_error.phpt
@@ -0,0 +1,33 @@
+--TEST--
+Test chroot() function error conditions with throw on error declare enabled - Non-existent directory
+--SKIPIF--
+<?php
+if (substr(PHP_OS, 0, 3) == 'WIN') {
+    die('skip.. Not valid for Windows');
+}
+
+if (!function_exists('chroot')) {
+    die('skip.. chroot() not defined in this build');
+}
+?>
+--FILE--
+<?php
+
+declare(throw_on_error=1);
+
+echo "*** Testing chroot() : error conditions ***\n";
+$directory = __DIR__ . '/idonotexist';
+
+echo "\n-- Pass chroot() an absolute path that does not exist --\n";
+try {
+    chroot($directory);
+} catch (\FileNotFound $e) {
+    echo $e->getMessage() . \PHP_EOL;
+}
+
+?>
+--EXPECTF--
+*** Testing chroot() : error conditions ***
+
+-- Pass chroot() an absolute path that does not exist --
+File not found: "%sidonotexist"
diff --git a/ext/standard/tests/dir/chroot_throw_on_error_file_in_path.phpt b/ext/standard/tests/dir/chroot_throw_on_error_file_in_path.phpt
new file mode 100644
index 0000000000000..4dc2f72ec5704
--- /dev/null
+++ b/ext/standard/tests/dir/chroot_throw_on_error_file_in_path.phpt
@@ -0,0 +1,33 @@
+--TEST--
+Test chroot() function error conditions with throw on error declare enabled - Non-existent directory
+--SKIPIF--
+<?php
+if (substr(PHP_OS, 0, 3) == 'WIN') {
+    die('skip.. Not valid for Windows');
+}
+
+if (!function_exists('chroot')) {
+    die('skip.. chroot() not defined in this build');
+}
+?>
+--FILE--
+<?php
+
+declare(throw_on_error=1);
+
+echo "*** Testing chroot() : error conditions ***\n";
+$directory = __FILE__;
+
+echo "\n-- Pass chroot() a non directory --\n";
+try {
+    chroot($directory);
+} catch (\NotDirectory $e) {
+    echo $e->getMessage() . \PHP_EOL;
+}
+
+?>
+--EXPECTF--
+*** Testing chroot() : error conditions ***
+
+-- Pass chroot() a non directory --
+"%schroot_throw_on_error_file_in_path.php" is not a directory