diff --git a/discord/flags.py b/discord/flags.py
index 841a9863f..b93a643e5 100644
--- a/discord/flags.py
+++ b/discord/flags.py
@@ -239,6 +239,12 @@ class SystemChannelFlags(BaseFlags):
                Returns an iterator of ``(name, value)`` pairs. This allows it
                to be, for example, constructed as a dict or a list of pairs.
 
+        .. describe:: bool(b)
+
+            Returns whether any flag is set to ``True``.
+
+            .. versionadded:: 2.0
+
     Attributes
     -----------
     value: :class:`int`
@@ -361,6 +367,12 @@ class MessageFlags(BaseFlags):
                Returns an iterator of ``(name, value)`` pairs. This allows it
                to be, for example, constructed as a dict or a list of pairs.
 
+        .. describe:: bool(b)
+
+            Returns whether any flag is set to ``True``.
+
+            .. versionadded:: 2.0
+
     .. versionadded:: 1.3
 
     Attributes
@@ -509,6 +521,12 @@ class PublicUserFlags(BaseFlags):
             to be, for example, constructed as a dict or a list of pairs.
             Note that aliases are not shown.
 
+        .. describe:: bool(b)
+
+            Returns whether any flag is set to ``True``.
+
+            .. versionadded:: 2.0
+
     .. versionadded:: 1.4
 
     Attributes
@@ -693,6 +711,12 @@ class Intents(BaseFlags):
                Returns an iterator of ``(name, value)`` pairs. This allows it
                to be, for example, constructed as a dict or a list of pairs.
 
+        .. describe:: bool(b)
+
+            Returns whether any intent is enabled.
+
+            .. versionadded:: 2.0
+
     Attributes
     -----------
     value: :class:`int`
@@ -1278,6 +1302,12 @@ class MemberCacheFlags(BaseFlags):
                Returns an iterator of ``(name, value)`` pairs. This allows it
                to be, for example, constructed as a dict or a list of pairs.
 
+        .. describe:: bool(b)
+
+            Returns whether any flag is set to ``True``.
+
+            .. versionadded:: 2.0
+
     Attributes
     -----------
     value: :class:`int`
@@ -1421,6 +1451,10 @@ class ApplicationFlags(BaseFlags):
             to be, for example, constructed as a dict or a list of pairs.
             Note that aliases are not shown.
 
+        .. describe:: bool(b)
+
+            Returns whether any flag is set to ``True``.
+
     .. versionadded:: 2.0
 
     Attributes
@@ -1556,6 +1590,10 @@ class ChannelFlags(BaseFlags):
             to be, for example, constructed as a dict or a list of pairs.
             Note that aliases are not shown.
 
+        .. describe:: bool(b)
+
+            Returns whether any flag is set to ``True``.
+
     .. versionadded:: 2.0
 
     Attributes
@@ -1652,6 +1690,10 @@ class AutoModPresets(ArrayFlags):
             to be, for example, constructed as a dict or a list of pairs.
             Note that aliases are not shown.
 
+        .. describe:: bool(b)
+
+            Returns whether any flag is set to ``True``.
+
     Attributes
     -----------
     value: :class:`int`
@@ -1736,6 +1778,10 @@ class MemberFlags(BaseFlags):
             to be, for example, constructed as a dict or a list of pairs.
             Note that aliases are not shown.
 
+        .. describe:: bool(b)
+
+            Returns whether any flag is set to ``True``.
+
 
     Attributes
     -----------
diff --git a/discord/permissions.py b/discord/permissions.py
index 6be0674c9..47c50c35f 100644
--- a/discord/permissions.py
+++ b/discord/permissions.py
@@ -119,6 +119,12 @@ class Permissions(BaseFlags):
                to be, for example, constructed as a dict or a list of pairs.
                Note that aliases are not shown.
 
+        .. describe:: bool(b)
+
+            Returns whether the permissions object has any permissions set to ``True``.
+
+            .. versionadded:: 2.0
+
     Attributes
     -----------
     value: :class:`int`
diff --git a/docs/migrating.rst b/docs/migrating.rst
index 8e31417fd..1a0b52158 100644
--- a/docs/migrating.rst
+++ b/docs/migrating.rst
@@ -1006,6 +1006,20 @@ Due to a breaking API change by Discord, :meth:`Guild.bans` no longer returns a
     async for ban in guild.bans(limit=1000):
         ...
 
+Flag classes now have a custom ``bool()`` implementation
+--------------------------------------------------------
+
+To allow library users to easily check whether an instance of a flag class has any flags enabled,
+using `bool` on them will now only return ``True`` if at least one flag is enabled.
+
+This means that evaluating instances of the following classes in a bool context (such as ``if obj:``) may no longer return ``True``:
+
+- :class:`Intents`
+- :class:`MemberCacheFlags`
+- :class:`MessageFlags`
+- :class:`Permissions`
+- :class:`PublicUserFlags`
+- :class:`SystemChannelFlags`
 
 Function Signature Changes
 ----------------------------