diff --git a/Engine/Settings.cs b/Engine/Settings.cs
index a4931978c..b0c424c64 100644
--- a/Engine/Settings.cs
+++ b/Engine/Settings.cs
@@ -497,6 +497,13 @@ private static bool IsBuiltinSettingPreset(object settingPreset)
         internal static SettingsMode FindSettingsMode(object settings, string path, out object settingsFound)
         {
             var settingsMode = SettingsMode.None;
+
+            // if the provided settings argument is wrapped in an expressions then PowerShell resolves it but it will be of type PSObject and we have to operate then on the BaseObject
+            if (settings is PSObject settingsFoundPSObject)
+            {
+                settings = settingsFoundPSObject.BaseObject;
+            }
+
             settingsFound = settings;
             if (settingsFound == null)
             {
@@ -532,11 +539,6 @@ internal static SettingsMode FindSettingsMode(object settings, string path, out
                     {
                         settingsMode = SettingsMode.Hashtable;
                     }
-                    // if the provided argument is wrapped in an expressions then PowerShell resolves it but it will be of type PSObject and we have to operate then on the BaseObject
-                    else if (settingsFound is PSObject settingsFoundPSObject)
-                    {
-                        TryResolveSettingForStringType(settingsFoundPSObject.BaseObject, ref settingsMode, ref settingsFound);
-                    }
                 }
             }
 
diff --git a/Tests/Engine/Settings.tests.ps1 b/Tests/Engine/Settings.tests.ps1
index 2e95bdd04..917b4ed8e 100644
--- a/Tests/Engine/Settings.tests.ps1
+++ b/Tests/Engine/Settings.tests.ps1
@@ -377,4 +377,34 @@ Describe "Settings Class" {
             @{ Expr = ';)' }
         )
     }
+
+    Context "FindSettingsMode" {
+        BeforeAll {
+            $findSettingsMode = ($settingsTypeName -as [type]).GetMethod(
+                'FindSettingsMode',
+                [System.Reflection.BindingFlags]::NonPublic -bor [System.Reflection.BindingFlags]::Static)
+
+            $outputObject = [System.Object]::new()
+        }
+
+        It "Should detect hashtable" {
+            $settings = @{}
+            $findSettingsMode.Invoke($null, @($settings, $null, [ref]$outputObject)) | Should -Be "Hashtable"
+        }
+
+        It "Should detect hashtable wrapped by a PSObject" {
+            $settings = [PSObject]@{} # Force the settings hashtable to be wrapped
+            $findSettingsMode.Invoke($null, @($settings, $null, [ref]$outputObject)) | Should -Be "Hashtable"
+        }
+
+        It "Should detect string" {
+            $settings = ""
+            $findSettingsMode.Invoke($null, @($settings, $null, [ref]$outputObject)) | Should -Be "File"
+        }
+
+        It "Should detect string wrapped by a PSObject" {
+            $settings = [PSObject]"" # Force the settings string to be wrapped
+            $findSettingsMode.Invoke($null, @($settings, $null, [ref]$outputObject)) | Should -Be "File"
+        }
+    }
 }