diff --git a/doc/ReleaseNotes.md b/doc/ReleaseNotes.md
index 2b818a30e1..d1358f5c5e 100644
--- a/doc/ReleaseNotes.md
+++ b/doc/ReleaseNotes.md
@@ -14,5 +14,6 @@ To use the feature, try `winget source edit winget-font` to set the Explicit sta
 <!-- Nothing yet! -->
 
 ## Bug Fixes
+* Portable Packages now use the correct directory separators regardless of which convention is used in the manifest
 * `--suppress-initial-details` now works with `winget configure test`
 * `--suppress-initial-details` no longer requires `--accept-configuration-agreements`
diff --git a/src/AppInstallerCLICore/PortableInstaller.cpp b/src/AppInstallerCLICore/PortableInstaller.cpp
index 141f0195cb..71b1bc2176 100644
--- a/src/AppInstallerCLICore/PortableInstaller.cpp
+++ b/src/AppInstallerCLICore/PortableInstaller.cpp
@@ -359,8 +359,11 @@ namespace AppInstaller::CLI::Portable
         }
     }
 
-    void PortableInstaller::AddToPathVariable(const std::filesystem::path& value)
+    void PortableInstaller::AddToPathVariable(std::filesystem::path value)
     {
+        // Ensure the preferred separator format
+        value.make_preferred();
+
         if (PathVariable(GetScope()).Append(value))
         {
             AICLI_LOG(Core, Info, << "Appending portable target directory to PATH registry: " << value);
@@ -372,7 +375,7 @@ namespace AppInstaller::CLI::Portable
         }
     }
 
-    void PortableInstaller::RemoveFromPathVariable(const std::filesystem::path& value)
+    void PortableInstaller::RemoveFromPathVariable(std::filesystem::path value)
     {
         if (std::filesystem::exists(value) && !std::filesystem::is_empty(value))
         {
@@ -380,7 +383,9 @@ namespace AppInstaller::CLI::Portable
         }
         else
         {
-            if (PathVariable(GetScope()).Remove(value))
+			// Attempt to remove both the original and the preferred format to ensure removal
+            // Necessary for handling old path values associated with winget-cli#5033
+            if (PathVariable(GetScope()).Remove(value) || PathVariable(GetScope()).Remove(value.make_preferred()))
             {
                 InstallDirectoryAddedToPath = false;
                 AICLI_LOG(CLI, Info, << "Removed target directory from PATH registry: " << value);
diff --git a/src/AppInstallerCLICore/PortableInstaller.h b/src/AppInstallerCLICore/PortableInstaller.h
index 5dec25063f..affdcc8756 100644
--- a/src/AppInstallerCLICore/PortableInstaller.h
+++ b/src/AppInstallerCLICore/PortableInstaller.h
@@ -113,7 +113,7 @@ namespace AppInstaller::CLI::Portable
         void CreateTargetInstallDirectory();
         void RemoveInstallDirectory();
 
-        void AddToPathVariable(const std::filesystem::path& value);
-        void RemoveFromPathVariable(const std::filesystem::path& value);
+        void AddToPathVariable(std::filesystem::path value);
+        void RemoveFromPathVariable(std::filesystem::path value);
     };
 }