diff --git a/src/Discord.Net.Core/Entities/Users/IGuildUser.cs b/src/Discord.Net.Core/Entities/Users/IGuildUser.cs
index 139640e5a..01ce78a24 100644
--- a/src/Discord.Net.Core/Entities/Users/IGuildUser.cs
+++ b/src/Discord.Net.Core/Entities/Users/IGuildUser.cs
@@ -6,7 +6,7 @@ using System.Threading.Tasks;
 namespace Discord
 {
     /// <summary> A Guild-User pairing. </summary>
-    public interface IGuildUser : IUser, IVoiceState, IComparable<IGuildUser>
+    public interface IGuildUser : IUser, IVoiceState, IComparable<IGuildUser>, IComparable<IRole>
     {
         /// <summary> Gets when this user joined this guild. </summary>
         DateTimeOffset? JoinedAt { get; }
diff --git a/src/Discord.Net.Core/Extensions/GuildUserExtensions.cs b/src/Discord.Net.Core/Extensions/GuildUserExtensions.cs
index 51e00fb42..b66a75b1f 100644
--- a/src/Discord.Net.Core/Extensions/GuildUserExtensions.cs
+++ b/src/Discord.Net.Core/Extensions/GuildUserExtensions.cs
@@ -22,10 +22,15 @@ namespace Discord
         }
 
         internal static int Compare(this IGuildUser u1, IGuildUser u2) {
+            // These should never be empty since the everyone role is always present
             var r1 = u1.GetRoles().Max();
             var r2 = u2.GetRoles().Max();
             var result = r1.CompareTo(r2);
             return result != 0 ? result : u1.Id.CompareTo(u2.Id);
         }
+
+        internal static int Compare(this IGuildUser user, IRole role) {
+            return user.GetRoles().Max().CompareTo(role);
+        }
     }
 }
diff --git a/src/Discord.Net.Rest/Entities/Users/RestGuildUser.cs b/src/Discord.Net.Rest/Entities/Users/RestGuildUser.cs
index 6e242e264..bebd245e6 100644
--- a/src/Discord.Net.Rest/Entities/Users/RestGuildUser.cs
+++ b/src/Discord.Net.Rest/Entities/Users/RestGuildUser.cs
@@ -98,6 +98,7 @@ namespace Discord.Rest
         }
     
         public int CompareTo(IGuildUser user) => this.Compare(user);
+        public int CompareTo(IRole role) => this.Compare(role);
 
         //IVoiceState
         bool IVoiceState.IsSelfDeafened => false;
diff --git a/src/Discord.Net.WebSocket/Entities/Users/SocketGuildUser.cs b/src/Discord.Net.WebSocket/Entities/Users/SocketGuildUser.cs
index 3610b6284..9c8165d30 100644
--- a/src/Discord.Net.WebSocket/Entities/Users/SocketGuildUser.cs
+++ b/src/Discord.Net.WebSocket/Entities/Users/SocketGuildUser.cs
@@ -97,6 +97,7 @@ namespace Discord.WebSocket
         ulong IGuildUser.GuildId => Guild.Id;
         IReadOnlyCollection<ulong> IGuildUser.RoleIds => RoleIds;
         public int CompareTo(IGuildUser user) => this.Compare(user);
+        public int CompareTo(IRole role) => this.Compare(role);
 
         //IUser
         Task<IDMChannel> IUser.GetDMChannelAsync(CacheMode mode, RequestOptions options)