diff --git a/src/System.Management.Automation/engine/Modules/ModuleIntrinsics.cs b/src/System.Management.Automation/engine/Modules/ModuleIntrinsics.cs
index e8b76de4837..cab7ed6c083 100644
--- a/src/System.Management.Automation/engine/Modules/ModuleIntrinsics.cs
+++ b/src/System.Management.Automation/engine/Modules/ModuleIntrinsics.cs
@@ -1139,7 +1139,7 @@ private static string AddToPath(string basePath, string pathToAdd, int insertPos
                     int position = PathContainsSubstring(result.ToString(), subPathToAdd); // searching in effective 'result' value ensures that possible duplicates in pathsToAdd are handled correctly
                     if (position == -1) // subPathToAdd not found - add it
                     {
-                        if (insertPosition == -1) // append subPathToAdd to the end
+                        if (insertPosition == -1 || insertPosition > basePath.Length) // append subPathToAdd to the end
                         {
                             bool endsWithPathSeparator = false;
                             if (result.Length > 0)
@@ -1223,23 +1223,23 @@ public static string GetModulePath(string currentProcessModulePath, string hklmM
                 // personalModulePath
                 // sharedModulePath
                 // systemModulePath
-                int insertIndex = 0;
-                if (!string.IsNullOrEmpty(personalModulePathToUse))
+                currentProcessModulePath = AddToPath(currentProcessModulePath, personalModulePathToUse, 0);
+                int insertIndex = currentProcessModulePath.IndexOf(Path.PathSeparator, PathContainsSubstring(currentProcessModulePath, personalModulePathToUse));
+                if (insertIndex != -1)
                 {
-                    currentProcessModulePath = AddToPath(currentProcessModulePath, personalModulePathToUse, insertIndex);
-                    insertIndex = PathContainsSubstring(currentProcessModulePath, personalModulePathToUse) + personalModulePathToUse.Length + 1;
+                    // advance past the path separator
+                    insertIndex++;
                 }
 
-                if (!string.IsNullOrEmpty(sharedModulePath))
+                currentProcessModulePath = AddToPath(currentProcessModulePath, sharedModulePath, insertIndex);
+                insertIndex = currentProcessModulePath.IndexOf(Path.PathSeparator, PathContainsSubstring(currentProcessModulePath, sharedModulePath));
+                if (insertIndex != -1)
                 {
-                    currentProcessModulePath = AddToPath(currentProcessModulePath, sharedModulePath, insertIndex);
-                    insertIndex = PathContainsSubstring(currentProcessModulePath, sharedModulePath) + sharedModulePath.Length + 1;
+                    // advance past the path separator
+                    insertIndex++;
                 }
 
-                if (!string.IsNullOrEmpty(systemModulePathToUse))
-                {
-                    currentProcessModulePath = AddToPath(currentProcessModulePath, systemModulePathToUse, insertIndex);
-                }
+                currentProcessModulePath = AddToPath(currentProcessModulePath, systemModulePathToUse, insertIndex);
             }
 
             return currentProcessModulePath;
diff --git a/test/powershell/engine/Module/ModulePath.Tests.ps1 b/test/powershell/engine/Module/ModulePath.Tests.ps1
index b4dd5add437..a18b4fc3ffa 100644
--- a/test/powershell/engine/Module/ModulePath.Tests.ps1
+++ b/test/powershell/engine/Module/ModulePath.Tests.ps1
@@ -187,4 +187,18 @@ Describe "SxS Module Path Basic Tests" -tags "CI" {
             Remove-Item -Path $userConfigPath -Force
         }
     }
+
+    It 'User PSModulePath has trailing separator' {
+        if ($IsWindows) {
+            $validation = "*\$env:SystemDrive\*"
+        }
+        else {
+            $validation = "*//*"
+        }
+
+        $newUserPath = Join-Path $expectedUserPath ([System.IO.Path]::DirectorySeparatorChar)
+        $env:PSModulePath = $env:PSModulePath.Replace($expectedUserPath, $newUserPath).Replace($expectedSharedPath,"")
+        $out = & $powershell -noprofile -command '$env:PSModulePath'
+        $out.Split([System.IO.Path]::PathSeparator, [System.StringSplitOptions]::RemoveEmptyEntries) | Should -Not -BeLike $validation
+    }
 }