diff --git a/src/Artemis.Core/Models/Profile/Conditions/DataModelConditionListPredicate.cs b/src/Artemis.Core/Models/Profile/Conditions/DataModelConditionListPredicate.cs
index 601483aef..a297c65c2 100644
--- a/src/Artemis.Core/Models/Profile/Conditions/DataModelConditionListPredicate.cs
+++ b/src/Artemis.Core/Models/Profile/Conditions/DataModelConditionListPredicate.cs
@@ -181,6 +181,24 @@ namespace Artemis.Core
             return true;
         }
 
+        /// <summary>
+        ///     Determines the best type to use for the right side op this predicate
+        /// </summary>
+        public Type? GetPreferredRightSideType()
+        {
+            Type? preferredType = Operator?.RightSideType;
+            Type? leftSideType = DataModelConditionList.IsPrimitiveList
+                ? DataModelConditionList.ListType
+                : LeftPath?.GetPropertyType();
+            if (preferredType == null)
+                return null;
+
+            if (leftSideType != null && preferredType.IsAssignableFrom(leftSideType))
+                preferredType = leftSideType;
+
+            return preferredType;
+        }
+
         #region IDisposable
 
         /// <inheritdoc />
@@ -411,13 +429,14 @@ namespace Artemis.Core
             }
 
             // If not null ensure the types match and if not, convert it
-            if (staticValue != null && staticValue.GetType() == Operator.RightSideType)
+            Type? preferredType = GetPreferredRightSideType();
+            if (staticValue != null && staticValue.GetType() == preferredType || preferredType == null)
                 RightStaticValue = staticValue;
             else if (staticValue != null)
-                RightStaticValue = Convert.ChangeType(staticValue, Operator.RightSideType);
+                RightStaticValue = Convert.ChangeType(staticValue, preferredType);
             // If null create a default instance for value types or simply make it null for reference types
-            else if (Operator.RightSideType.IsValueType)
-                RightStaticValue = Activator.CreateInstance(Operator.RightSideType);
+            else if (preferredType.IsValueType)
+                RightStaticValue = Activator.CreateInstance(preferredType);
             else
                 RightStaticValue = null;
         }
diff --git a/src/Artemis.Core/Models/Profile/Conditions/DataModelConditionPredicate.cs b/src/Artemis.Core/Models/Profile/Conditions/DataModelConditionPredicate.cs
index db96b8c22..72b693f5d 100644
--- a/src/Artemis.Core/Models/Profile/Conditions/DataModelConditionPredicate.cs
+++ b/src/Artemis.Core/Models/Profile/Conditions/DataModelConditionPredicate.cs
@@ -1,6 +1,4 @@
 using System;
-using System.IO;
-using Artemis.Core.DataModelExpansions;
 using Artemis.Storage.Entities.Profile.Abstract;
 using Artemis.Storage.Entities.Profile.Conditions;
 using Newtonsoft.Json;
@@ -113,6 +111,7 @@ namespace Artemis.Core
                 RightStaticValue = staticValue;
                 return;
             }
+
             // If the operator does not support a right side, always set it to null
             if (Operator.RightSideType == null)
             {
@@ -121,13 +120,14 @@ namespace Artemis.Core
             }
 
             // If not null ensure the types match and if not, convert it
-            if (staticValue != null && staticValue.GetType() == Operator.RightSideType)
+            Type? preferredType = GetPreferredRightSideType();
+            if (staticValue != null && staticValue.GetType() == preferredType || preferredType == null)
                 RightStaticValue = staticValue;
             else if (staticValue != null)
-                RightStaticValue = Convert.ChangeType(staticValue, Operator.RightSideType);
+                RightStaticValue = Convert.ChangeType(staticValue, preferredType);
             // If null create a default instance for value types or simply make it null for reference types
-            else if (Operator.RightSideType.IsValueType)
-                RightStaticValue = Activator.CreateInstance(Operator.RightSideType);
+            else if (preferredType.IsValueType)
+                RightStaticValue = Activator.CreateInstance(preferredType);
             else
                 RightStaticValue = null;
         }
@@ -184,6 +184,22 @@ namespace Artemis.Core
             return Operator.InternalEvaluate(LeftPath.GetValue(), RightPath.GetValue());
         }
 
+        /// <summary>
+        ///     Determines the best type to use for the right side op this predicate
+        /// </summary>
+        public Type? GetPreferredRightSideType()
+        {
+            Type? preferredType = Operator?.RightSideType;
+            Type? leftSideType = LeftPath?.GetPropertyType();
+            if (preferredType == null)
+                return null;
+
+            if (leftSideType != null && preferredType.IsAssignableFrom(leftSideType))
+                preferredType = leftSideType;
+
+            return preferredType;
+        }
+
         /// <inheritdoc />
         public override string ToString()
         {
diff --git a/src/Artemis.UI.Shared/DataModelVisualization/Input/DataModelStaticViewModel.cs b/src/Artemis.UI.Shared/DataModelVisualization/Input/DataModelStaticViewModel.cs
index 343f01028..11c993fc9 100644
--- a/src/Artemis.UI.Shared/DataModelVisualization/Input/DataModelStaticViewModel.cs
+++ b/src/Artemis.UI.Shared/DataModelVisualization/Input/DataModelStaticViewModel.cs
@@ -69,7 +69,7 @@ namespace Artemis.UI.Shared.Input
         public Type TargetType
         {
             get => _targetType;
-            set => SetAndNotify(ref _targetType, value);
+            private set => SetAndNotify(ref _targetType, value);
         }
 
         public DataModelPropertyAttribute TargetDescription
diff --git a/src/Artemis.UI/Screens/ProfileEditor/Conditions/DataModelConditionListPredicateViewModel.cs b/src/Artemis.UI/Screens/ProfileEditor/Conditions/DataModelConditionListPredicateViewModel.cs
index 658ac8c92..535bdb323 100644
--- a/src/Artemis.UI/Screens/ProfileEditor/Conditions/DataModelConditionListPredicateViewModel.cs
+++ b/src/Artemis.UI/Screens/ProfileEditor/Conditions/DataModelConditionListPredicateViewModel.cs
@@ -156,14 +156,16 @@ namespace Artemis.UI.Screens.ProfileEditor.Conditions
             {
                 DisposeRightSideDynamicViewModel();
                 if (RightSideInputViewModel == null)
-                    CreateRightSideInputViewModel(SelectedOperator.RightSideType);
+                    CreateRightSideInputViewModel();
 
                 if (SelectedOperator.RightSideType.IsValueType && DataModelConditionListPredicate.RightStaticValue == null)
                     RightSideInputViewModel.Value = SelectedOperator.RightSideType.GetDefault();
                 else
                     RightSideInputViewModel.Value = DataModelConditionListPredicate.RightStaticValue;
-                if (RightSideInputViewModel.TargetType != SelectedOperator.RightSideType)
-                    RightSideInputViewModel.UpdateTargetType(SelectedOperator.RightSideType);
+
+                Type preferredType = DataModelConditionListPredicate.GetPreferredRightSideType();
+                if (RightSideInputViewModel.TargetType != preferredType)
+                    RightSideInputViewModel.UpdateTargetType(preferredType);
             }
         }
 
@@ -222,7 +224,7 @@ namespace Artemis.UI.Screens.ProfileEditor.Conditions
             SelectedOperator = dataModelConditionOperator;
             ApplyOperator();
         }
-
+        
         #region IDisposable
 
         public void Dispose()
@@ -286,9 +288,10 @@ namespace Artemis.UI.Screens.ProfileEditor.Conditions
                 RightSideSelectionViewModel.ExtraDataModelViewModels.Add(listValue);
         }
 
-        private void CreateRightSideInputViewModel(Type leftSideType)
+        private void CreateRightSideInputViewModel()
         {
-            RightSideInputViewModel = _dataModelUIService.GetStaticInputViewModel(leftSideType, LeftSideSelectionViewModel.DataModelPath?.GetPropertyDescription());
+            Type preferredType = DataModelConditionListPredicate.GetPreferredRightSideType();
+            RightSideInputViewModel = _dataModelUIService.GetStaticInputViewModel(preferredType, LeftSideSelectionViewModel.DataModelPath?.GetPropertyDescription());
             RightSideInputViewModel.ButtonBrush = (SolidColorBrush) Application.Current.FindResource("PrimaryHueMidBrush");
             RightSideInputViewModel.DisplaySwitchButton = true;
             RightSideInputViewModel.ValueUpdated += RightSideOnValueEntered;
diff --git a/src/Artemis.UI/Screens/ProfileEditor/Conditions/DataModelConditionPredicateViewModel.cs b/src/Artemis.UI/Screens/ProfileEditor/Conditions/DataModelConditionPredicateViewModel.cs
index a67214d63..4f1fa2f08 100644
--- a/src/Artemis.UI/Screens/ProfileEditor/Conditions/DataModelConditionPredicateViewModel.cs
+++ b/src/Artemis.UI/Screens/ProfileEditor/Conditions/DataModelConditionPredicateViewModel.cs
@@ -131,14 +131,16 @@ namespace Artemis.UI.Screens.ProfileEditor.Conditions
             {
                 DisposeRightSideDynamicViewModel();
                 if (RightSideInputViewModel == null)
-                    CreateRightSideInputViewModel(SelectedOperator.RightSideType);
+                    CreateRightSideInputViewModel();
 
                 if (SelectedOperator.RightSideType.IsValueType && DataModelConditionPredicate.RightStaticValue == null)
                     RightSideInputViewModel.Value = SelectedOperator.RightSideType.GetDefault();
                 else
                     RightSideInputViewModel.Value = DataModelConditionPredicate.RightStaticValue;
-                if (RightSideInputViewModel.TargetType != SelectedOperator.RightSideType)
-                    RightSideInputViewModel.UpdateTargetType(SelectedOperator.RightSideType);
+
+                Type preferredType = DataModelConditionPredicate.GetPreferredRightSideType();
+                if (RightSideInputViewModel.TargetType != preferredType)
+                    RightSideInputViewModel.UpdateTargetType(preferredType);
             }
         }
 
@@ -188,7 +190,7 @@ namespace Artemis.UI.Screens.ProfileEditor.Conditions
             SelectedOperator = DataModelConditionOperator;
             ApplyOperator();
         }
-
+        
         #region IDisposable
 
         public void Dispose()
@@ -217,9 +219,10 @@ namespace Artemis.UI.Screens.ProfileEditor.Conditions
             RightSideSelectionViewModel.SwitchToStaticRequested += RightSideSelectionViewModelOnSwitchToStaticRequested;
         }
 
-        private void CreateRightSideInputViewModel(Type leftSideType)
+        private void CreateRightSideInputViewModel()
         {
-            RightSideInputViewModel = _dataModelUIService.GetStaticInputViewModel(leftSideType, LeftSideSelectionViewModel.DataModelPath?.GetPropertyDescription());
+            Type preferredType = DataModelConditionPredicate.GetPreferredRightSideType();
+            RightSideInputViewModel = _dataModelUIService.GetStaticInputViewModel(preferredType, LeftSideSelectionViewModel.DataModelPath?.GetPropertyDescription());
             RightSideInputViewModel.ButtonBrush = (SolidColorBrush) Application.Current.FindResource("PrimaryHueMidBrush");
             RightSideInputViewModel.DisplaySwitchButton = true;
             RightSideInputViewModel.ValueUpdated += RightSideOnValueEntered;