diff --git a/changelog/1238.feature.rst b/changelog/1238.feature.rst
new file mode 100644
index 0000000000..29445fc514
--- /dev/null
+++ b/changelog/1238.feature.rst
@@ -0,0 +1 @@
+Add support for ``BaseFlags`` to allow comparison with ``flag_values`` and vice versa.
diff --git a/disnake/flags.py b/disnake/flags.py
index de753b30ba..6b2c24e71c 100644
--- a/disnake/flags.py
+++ b/disnake/flags.py
@@ -55,6 +55,16 @@ def __init__(self, func: Callable[[Any], int]) -> None:
         self.__doc__ = func.__doc__
         self._parent: Type[T] = MISSING
 
+    def __eq__(self, other: Any) -> bool:
+        if isinstance(other, flag_value):
+            return self.flag == other.flag
+        if isinstance(other, BaseFlags):
+            return self._parent is other.__class__ and self.flag == other.value
+        return False
+
+    def __ne__(self, other: Any) -> bool:
+        return not self.__eq__(other)
+
     def __or__(self, other: Union[flag_value[T], T]) -> T:
         if isinstance(other, BaseFlags):
             if self._parent is not other.__class__:
@@ -148,7 +158,11 @@ def _from_value(cls, value: int) -> Self:
         return self
 
     def __eq__(self, other: Any) -> bool:
-        return isinstance(other, self.__class__) and self.value == other.value
+        if isinstance(other, self.__class__):
+            return self.value == other.value
+        if isinstance(other, flag_value):
+            return self.__class__ is other._parent and self.value == other.flag
+        return False
 
     def __ne__(self, other: Any) -> bool:
         return not self.__eq__(other)
diff --git a/tests/test_flags.py b/tests/test_flags.py
index cb9d64b0ea..575851c26e 100644
--- a/tests/test_flags.py
+++ b/tests/test_flags.py
@@ -184,6 +184,21 @@ def test__eq__(self) -> None:
         assert not ins == other
         assert ins != other
 
+    def test__eq__flag_value(self) -> None:
+        ins = TestFlags(one=True)
+        other = TestFlags(one=True, two=True)
+
+        assert ins == TestFlags.one
+        assert TestFlags.one == ins
+
+        assert not ins != TestFlags.one
+        assert ins != TestFlags.two
+
+        assert other != TestFlags.one
+        assert other != TestFlags.two
+
+        assert other == TestFlags.three
+
     def test__and__(self) -> None:
         ins = TestFlags(one=True, two=True)
         other = TestFlags(one=True, two=True)