diff --git a/news/400.feature b/news/400.feature
new file mode 100644
index 000000000..95e5c300b
--- /dev/null
+++ b/news/400.feature
@@ -0,0 +1 @@
+flag_override can now override multiple flags at the same time
diff --git a/omegaconf/omegaconf.py b/omegaconf/omegaconf.py
index df681b1ab..b063a2ddb 100644
--- a/omegaconf/omegaconf.py
+++ b/omegaconf/omegaconf.py
@@ -708,14 +708,21 @@ def to_yaml(cfg: Any, *, resolve: bool = False, sort_keys: bool = False) -> str:
 
 @contextmanager
 def flag_override(
-    config: Node, name: str, value: Optional[bool]
+    config: Node, names: Union[List[str], str], value: Optional[bool]
 ) -> Generator[Node, None, None]:
-    prev_state = config._get_flag(name)
+
+    if isinstance(names, str):
+        names = [names]
+
+    prev_states = [config._get_flag(name) for name in names]
+
     try:
-        config._set_flag(name, value)
+        for idx, name in enumerate(names):
+            config._set_flag(name, value)
         yield config
     finally:
-        config._set_flag(name, prev_state)
+        for idx, name in enumerate(names):
+            config._set_flag(name, prev_states[idx])
 
 
 @contextmanager
diff --git a/tests/test_base_config.py b/tests/test_base_config.py
index cd21df7cb..fc343d26f 100644
--- a/tests/test_base_config.py
+++ b/tests/test_base_config.py
@@ -18,7 +18,7 @@
     open_dict,
     read_write,
 )
-from omegaconf.errors import ConfigKeyError
+from omegaconf.errors import ConfigAttributeError, ConfigKeyError
 
 from . import Color, StructuredWithMissing, User, does_not_raise
 
@@ -440,6 +440,24 @@ def test_flag_override(
             func(c)
 
 
+def test_multiple_flags_override() -> None:
+    c = OmegaConf.create({"foo": "bar"})
+    with flag_override(c, ["readonly"], True):
+        with pytest.raises(ReadonlyConfigError):
+            c.foo = 10
+
+    with flag_override(c, ["struct"], True):
+        with pytest.raises(ConfigAttributeError):
+            c.x = 10
+
+    with flag_override(c, ["struct", "readonly"], True):
+        with pytest.raises(ConfigAttributeError):
+            c.x = 10
+
+        with pytest.raises(ReadonlyConfigError):
+            c.foo = 20
+
+
 @pytest.mark.parametrize(  # type: ignore
     "src, func, expectation",
     [