diff --git a/Modules.Interfaces/ActiveDirectoryInterface/SyncUsers.MSSQL.vb b/Modules.Interfaces/ActiveDirectoryInterface/SyncUsers.MSSQL.vb
index 3e4dbe5d..1d57e2d3 100644
--- a/Modules.Interfaces/ActiveDirectoryInterface/SyncUsers.MSSQL.vb
+++ b/Modules.Interfaces/ActiveDirectoryInterface/SyncUsers.MSSQL.vb
@@ -20,6 +20,8 @@ Namespace SyncUsers
         Public Function SyncUsers(GroupName As String, Users As List(Of ADUser), PropertyMapping As List(Of AttributeMapping)) As List(Of ADUser) Implements ISyncUsers.SyncUsers
             Dim oGroupId As Integer
             Dim oSyncedUsers As New List(Of ADUser)
+            Dim oSyncedUserIds As New List(Of Int64)
+
             Dim oCreatedUsers As New List(Of ADUser)
             Dim oUpdatedUsers As New List(Of ADUser)
 
@@ -40,7 +42,7 @@ Namespace SyncUsers
 
             For Each oUser In Users
                 Dim oUserId As Int64
-                Dim oUserExists As Boolean = False
+                Dim oUserExists As Boolean
 
                 ' Check if user already exists
                 Try
@@ -54,6 +56,11 @@ Namespace SyncUsers
                     Continue For
                 End Try
 
+                ' Collect user ids from existing users
+                If oUserExists Then
+                    oSyncedUserIds.Add(oUserId)
+                End If
+
                 ' Create or update user
                 Try
                     If Not oUserExists Then
@@ -99,6 +106,11 @@ Namespace SyncUsers
                 oSyncedUsers.Add(oUser)
             Next
 
+            Dim oUserIdString = String.Join(",", oSyncedUserIds)
+            Dim oSQL As String = $"SELECT COUNT(*) FROM TBDD_GROUPS_USER WHERE USER_ID NOT IN (${oUserIdString}) AND GROUP_ID = {oGroupId}"
+            Dim oDeletedRelations = _mssql.GetScalarValue(oSQL)
+
+            _logger.Info("Deleted [{0}] user to group relations [TEST RUN]", oDeletedRelations)
             _logger.Info("Created [{0}] new users", oCreatedUsers.Count)
             _logger.Info("Updated [{0}] users", oUpdatedUsers.Count)