diff --git a/scripts/Windows/Scripts/Context.ps1 b/scripts/Windows/Scripts/Context.ps1
index 32670ffa8..041100768 100644
--- a/scripts/Windows/Scripts/Context.ps1
+++ b/scripts/Windows/Scripts/Context.ps1
@@ -47,13 +47,18 @@ class Context {
         }
 
         $profileFiles | ForEach-Object {
-            $dirName = Split-Path -Parent $_;
+            $fileName = "C:\Users\Default\$_";
+            $dirName = Split-Path -Parent $fileName;
 
             if (-not (Test-Path -PathType Container $dirName)) {
                 New-Item -ItemType Directory $dirName;
             }
 
-            Add-Content -Force "C:\Users\Default\$_" "`n$statement";
+            if (Test-Path -PathType Leaf $fileName) {
+                Add-Content -Force "$fileName" "`n$statement";
+            } else {
+                Set-Content -Force "$fileName" "$statement";
+            }
         };
 
         Pop-Location;