diff --git a/src/DynamoCoreWpf/ViewModels/Preview/WatchViewModel.cs b/src/DynamoCoreWpf/ViewModels/Preview/WatchViewModel.cs
index 9d4b692b4b4..19f8e2bdbed 100644
--- a/src/DynamoCoreWpf/ViewModels/Preview/WatchViewModel.cs
+++ b/src/DynamoCoreWpf/ViewModels/Preview/WatchViewModel.cs
@@ -153,7 +153,6 @@ public bool IsOneRowContent
             }
         }
 
-
         /// <summary>
         /// Number of items in the overall list if node output is a list
         /// </summary>
@@ -256,13 +255,17 @@ private Tuple<int, int> GetMaximumDepthAndItemNumber(WatchViewModel wvm)
             {
                 return GetMaximumDepthAndItemNumber(wvm.Children[0]);
             }
-            else
+
+            // if it's a list, recurse
+            if (wvm.NodeLabel == LIST)
             {
                 var depthAndNumbers = wvm.Children.Select(GetMaximumDepthAndItemNumber);
                 var maxDepth = depthAndNumbers.Select(t => t.Item1).DefaultIfEmpty(1).Max() + 1;
                 var itemNumber = depthAndNumbers.Select(t => t.Item2).Sum();
                 return new Tuple<int, int>(maxDepth, itemNumber);
             }
+
+            return new Tuple<int, int>(1,1);
         }
 
         /// <summary>
diff --git a/test/DynamoCoreWpfTests/WatchNodeTests.cs b/test/DynamoCoreWpfTests/WatchNodeTests.cs
index 5059ade3e3d..f49abdbd314 100644
--- a/test/DynamoCoreWpfTests/WatchNodeTests.cs
+++ b/test/DynamoCoreWpfTests/WatchNodeTests.cs
@@ -230,5 +230,25 @@ public void WatchFunctionObject_collection_5033()
 
             Assert.AreEqual("Function", watchVM.NodeLabel);
         }
+
+        [Test]
+        public void WatchNestedDictionary()
+        {
+            string openPath = Path.Combine(TestDirectory, @"core\watch\watchNestedDictionaryList.dyn");
+            ViewModel.OpenCommand.Execute(openPath);
+            ViewModel.HomeSpace.Run();
+
+            var watchNode = ViewModel.Model.CurrentWorkspace.FirstNodeFromWorkspace<CodeBlockNodeModel>();
+            var watchVM = ViewModel.WatchHandler.GenerateWatchViewModelForData(
+                watchNode.CachedValue,
+                ViewModel.Model.EngineController.LiveRunnerRuntimeCore,
+                watchNode.AstIdentifierForPreview.Name);
+
+            watchVM.CountNumberOfItems();
+            watchVM.CountLevels();
+
+            Assert.AreEqual(3, watchVM.Levels.ElementAt(0));
+            Assert.AreEqual(2, watchVM.NumberOfItems);
+        }
     }
 }
diff --git a/test/core/watch/watchNestedDictionaryList.dyn b/test/core/watch/watchNestedDictionaryList.dyn
new file mode 100644
index 00000000000..79152c51424
--- /dev/null
+++ b/test/core/watch/watchNestedDictionaryList.dyn
@@ -0,0 +1,76 @@
+{
+  "Uuid": "b3971a38-9e42-4229-9ebd-7fa012a6ac9b",
+  "IsCustomNode": false,
+  "Description": null,
+  "Name": "watchNestedDictionaryList",
+  "ElementResolver": {
+    "ResolutionMap": {
+      "DesignScript.Builtin.Dictionary": {
+        "Key": "DesignScript.Builtin.Dictionary",
+        "Value": "Builtin.dll"
+      }
+    }
+  },
+  "Inputs": [],
+  "Nodes": [
+    {
+      "ConcreteType": "Dynamo.Graph.Nodes.CodeBlockNodeModel, DynamoCore",
+      "NodeType": "CodeBlockNode",
+      "Code": "[[{\"foo\": [1,2]}, {\"bar\": [1,2,3,4], \"baz\": 1}]];",
+      "Id": "937132ee84a64220b496e9f7d86f477a",
+      "Inputs": [],
+      "Outputs": [
+        {
+          "Id": "65eb03b27fd64885a55e921c23592d61",
+          "Name": "",
+          "Description": "Value of expression at line 1",
+          "UsingDefaultValue": false,
+          "Level": 2,
+          "UseLevels": false,
+          "KeepListStructure": false
+        }
+      ],
+      "Replication": "Disabled",
+      "Description": "Allows for DesignScript code to be authored directly"
+    }
+  ],
+  "Connectors": [],
+  "Dependencies": [],
+  "Bindings": [],
+  "View": {
+    "Dynamo": {
+      "ScaleFactor": 1.0,
+      "HasRunWithoutCrash": true,
+      "IsVisibleInDynamoLibrary": true,
+      "Version": "2.0.0.2821",
+      "RunType": "Automatic",
+      "RunPeriod": "1000"
+    },
+    "Camera": {
+      "Name": "Default Camera",
+      "EyeX": -17.0,
+      "EyeY": 24.0,
+      "EyeZ": 50.0,
+      "LookX": 12.0,
+      "LookY": -13.0,
+      "LookZ": -58.0,
+      "UpX": 0.0,
+      "UpY": 1.0,
+      "UpZ": 0.0
+    },
+    "NodeViews": [
+      {
+        "ShowGeometry": true,
+        "Name": "Code Block",
+        "Id": "937132ee84a64220b496e9f7d86f477a",
+        "Excluded": false,
+        "X": 119.0,
+        "Y": 213.0
+      }
+    ],
+    "Annotations": [],
+    "X": 0.0,
+    "Y": 0.0,
+    "Zoom": 1.0
+  }
+}
\ No newline at end of file