diff --git a/src/Kook.Net.Rest/Entities/Channels/ChannelHelper.cs b/src/Kook.Net.Rest/Entities/Channels/ChannelHelper.cs
index afe2c0d8..475b0b08 100644
--- a/src/Kook.Net.Rest/Entities/Channels/ChannelHelper.cs
+++ b/src/Kook.Net.Rest/Entities/Channels/ChannelHelper.cs
@@ -514,7 +514,9 @@ public static async Task<UserPermissionOverwrite> ModifyPermissionOverwriteAsync
         IGuildUser user, Func<OverwritePermissions, OverwritePermissions> func, RequestOptions options)
     {
         OverwritePermissions? perms = channel.UserPermissionOverwrites.SingleOrDefault(x => x.Target.Id == user.Id)?.Permissions;
-        if (!perms.HasValue) return null;
+        if (!perms.HasValue)
+            throw new ArgumentNullException(nameof(user),
+                "The user does not have any permission overwrites on this channel.");
 
         perms = func(perms.Value);
         ModifyChannelPermissionOverwriteParams args = new(channel.Id, PermissionOverwriteTargetType.User,
@@ -530,7 +532,9 @@ public static async Task<RolePermissionOverwrite> ModifyPermissionOverwriteAsync
         IRole role, Func<OverwritePermissions, OverwritePermissions> func, RequestOptions options)
     {
         OverwritePermissions? perms = channel.RolePermissionOverwrites.SingleOrDefault(x => x.Target == role.Id)?.Permissions;
-        if (!perms.HasValue) return null;
+        if (!perms.HasValue)
+            throw new ArgumentNullException(nameof(role),
+                "The role does not have any permission overwrites on this channel.");
 
         perms = func(perms.Value);
         ModifyChannelPermissionOverwriteParams args = new(channel.Id, PermissionOverwriteTargetType.Role,
diff --git a/src/Kook.Net.WebSocket/Entities/Channels/SocketGuildChannel.cs b/src/Kook.Net.WebSocket/Entities/Channels/SocketGuildChannel.cs
index 3cb41443..cae91948 100644
--- a/src/Kook.Net.WebSocket/Entities/Channels/SocketGuildChannel.cs
+++ b/src/Kook.Net.WebSocket/Entities/Channels/SocketGuildChannel.cs
@@ -170,8 +170,11 @@ public Task DeleteAsync(RequestOptions options = null)
     /// <returns>
     ///     A task representing the asynchronous permission operation for adding the specified permissions to the channel.
     /// </returns>
-    public async Task AddPermissionOverwriteAsync(IGuildUser user, RequestOptions options = null) =>
-        await ChannelHelper.AddPermissionOverwriteAsync(this, Kook, user, options).ConfigureAwait(false);
+    public async Task AddPermissionOverwriteAsync(IGuildUser user, RequestOptions options = null)
+    {
+        UserPermissionOverwrite perms = await ChannelHelper.AddPermissionOverwriteAsync(this, Kook, user, options).ConfigureAwait(false);
+        _userPermissionOverwrites = _userPermissionOverwrites.Add(perms);
+    }
 
     /// <summary>
     ///     Adds or updates the permission overwrite for the given role.
@@ -181,8 +184,11 @@ public async Task AddPermissionOverwriteAsync(IGuildUser user, RequestOptions op
     /// <returns>
     ///     A task representing the asynchronous permission operation for adding the specified permissions to the channel.
     /// </returns>
-    public async Task AddPermissionOverwriteAsync(IRole role, RequestOptions options = null) =>
-        await ChannelHelper.AddPermissionOverwriteAsync(this, Kook, role, options).ConfigureAwait(false);
+    public async Task AddPermissionOverwriteAsync(IRole role, RequestOptions options = null)
+    {
+        RolePermissionOverwrite perms = await ChannelHelper.AddPermissionOverwriteAsync(this, Kook, role, options).ConfigureAwait(false);
+        _rolePermissionOverwrites = _rolePermissionOverwrites.Add(perms);
+    }
 
     /// <summary>
     ///     Removes the permission overwrite for the given user, if one exists.
@@ -192,9 +198,18 @@ public async Task AddPermissionOverwriteAsync(IRole role, RequestOptions options
     /// <returns>
     ///     A task representing the asynchronous operation for removing the specified permissions from the channel.
     /// </returns>
-    public async Task RemovePermissionOverwriteAsync(IGuildUser user, RequestOptions options = null) =>
+    public async Task RemovePermissionOverwriteAsync(IGuildUser user, RequestOptions options = null)
+    {
         await ChannelHelper.RemovePermissionOverwriteAsync(this, Kook, user, options).ConfigureAwait(false);
 
+        for (int i = 0; i < _userPermissionOverwrites.Length; i++)
+            if (_userPermissionOverwrites[i].Target.Id == user.Id)
+            {
+                _userPermissionOverwrites = _userPermissionOverwrites.RemoveAt(i);
+                return;
+            }
+    }
+
     /// <summary>
     ///     Removes the permission overwrite for the given role, if one exists.
     /// </summary>
@@ -203,9 +218,18 @@ public async Task RemovePermissionOverwriteAsync(IGuildUser user, RequestOptions
     /// <returns>
     ///     A task representing the asynchronous operation for removing the specified permissions from the channel.
     /// </returns>
-    public async Task RemovePermissionOverwriteAsync(IRole role, RequestOptions options = null) =>
+    public async Task RemovePermissionOverwriteAsync(IRole role, RequestOptions options = null)
+    {
         await ChannelHelper.RemovePermissionOverwriteAsync(this, Kook, role, options).ConfigureAwait(false);
 
+        for (int i = 0; i < _rolePermissionOverwrites.Length; i++)
+            if (_rolePermissionOverwrites[i].Target == role.Id)
+            {
+                _rolePermissionOverwrites = _rolePermissionOverwrites.RemoveAt(i);
+                return;
+            }
+    }
+
     /// <summary>
     ///     Updates the permission overwrite for the given user, if one exists.
     /// </summary>
@@ -215,9 +239,18 @@ public async Task RemovePermissionOverwriteAsync(IRole role, RequestOptions opti
     /// <returns>
     ///     A task representing the asynchronous operation for removing the specified permissions from the channel.
     /// </returns>
-    public async Task ModifyPermissionOverwriteAsync(IGuildUser user, Func<OverwritePermissions, OverwritePermissions> func,
-        RequestOptions options = null) =>
-        await ChannelHelper.ModifyPermissionOverwriteAsync(this, Kook, user, func, options).ConfigureAwait(false);
+    public async Task ModifyPermissionOverwriteAsync(IGuildUser user, Func<OverwritePermissions, OverwritePermissions> func, RequestOptions options = null)
+    {
+        UserPermissionOverwrite perms = await ChannelHelper.ModifyPermissionOverwriteAsync(this, Kook, user, func, options).ConfigureAwait(false);
+
+        for (int i = 0; i < _userPermissionOverwrites.Length; i++)
+            if (_userPermissionOverwrites[i].Target.Id == user.Id)
+            {
+                _userPermissionOverwrites = _userPermissionOverwrites.RemoveAt(i);
+                _userPermissionOverwrites = _userPermissionOverwrites.Add(perms);
+                return;
+            }
+    }
 
     /// <summary>
     ///     Updates the permission overwrite for the given role, if one exists.
@@ -228,9 +261,18 @@ public async Task ModifyPermissionOverwriteAsync(IGuildUser user, Func<Overwrite
     /// <returns>
     ///     A task representing the asynchronous operation for removing the specified permissions from the channel.
     /// </returns>
-    public async Task
-        ModifyPermissionOverwriteAsync(IRole role, Func<OverwritePermissions, OverwritePermissions> func, RequestOptions options = null) =>
-        await ChannelHelper.ModifyPermissionOverwriteAsync(this, Kook, role, func, options).ConfigureAwait(false);
+    public async Task ModifyPermissionOverwriteAsync(IRole role, Func<OverwritePermissions, OverwritePermissions> func, RequestOptions options = null)
+    {
+        RolePermissionOverwrite perms = await ChannelHelper.ModifyPermissionOverwriteAsync(this, Kook, role, func, options).ConfigureAwait(false);
+
+        for (int i = 0; i < _rolePermissionOverwrites.Length; i++)
+            if (_rolePermissionOverwrites[i].Target == role.Id)
+            {
+                _rolePermissionOverwrites = _rolePermissionOverwrites.RemoveAt(i);
+                _rolePermissionOverwrites = _rolePermissionOverwrites.Add(perms);
+                return;
+            }
+    }
 
     /// <summary>
     ///     Gets a <see cref="SocketGuildUser"/> from this channel.