diff --git a/src/chocolatey/infrastructure.app/services/ChocolateyPackageService.cs b/src/chocolatey/infrastructure.app/services/ChocolateyPackageService.cs
index a112ac9b36..a59879659c 100644
--- a/src/chocolatey/infrastructure.app/services/ChocolateyPackageService.cs
+++ b/src/chocolatey/infrastructure.app/services/ChocolateyPackageService.cs
@@ -703,7 +703,10 @@ private void rollback_previous_version(ChocolateyConfiguration config, PackageRe
                 }
             }
 
+            rollbackDirectory = _fileSystem.get_full_path(rollbackDirectory);
+            
             if (string.IsNullOrWhiteSpace(rollbackDirectory) || !_fileSystem.directory_exists(rollbackDirectory)) return;
+            if (!rollbackDirectory.StartsWith(ApplicationParameters.PackageBackupLocation) || rollbackDirectory.is_equal_to(ApplicationParameters.PackageBackupLocation)) return;
 
             this.Log().Debug("Attempting rollback");
 
diff --git a/src/chocolatey/infrastructure.app/services/NugetService.cs b/src/chocolatey/infrastructure.app/services/NugetService.cs
index de24741f83..f08f9768ff 100644
--- a/src/chocolatey/infrastructure.app/services/NugetService.cs
+++ b/src/chocolatey/infrastructure.app/services/NugetService.cs
@@ -376,7 +376,7 @@ public ConcurrentDictionary<string, PackageResult> install_run(ChocolateyConfigu
 
         public void remove_rollback_directory_if_exists(string packageName)
         {
-            var rollbackDirectory = _fileSystem.combine_paths(ApplicationParameters.PackageBackupLocation, packageName);
+            var rollbackDirectory = _fileSystem.get_full_path(_fileSystem.combine_paths(ApplicationParameters.PackageBackupLocation, packageName));
             if (!_fileSystem.directory_exists(rollbackDirectory))
             {
                 //search for folder
@@ -385,10 +385,13 @@ public void remove_rollback_directory_if_exists(string packageName)
                 {
                     rollbackDirectory = possibleRollbacks.OrderByDescending(p => p).DefaultIfEmpty(string.Empty).FirstOrDefault();
                 }
-            }
 
+                rollbackDirectory = _fileSystem.get_full_path(rollbackDirectory);
+            }
+            
             if (string.IsNullOrWhiteSpace(rollbackDirectory) || !_fileSystem.directory_exists(rollbackDirectory)) return;
-
+            if (!rollbackDirectory.StartsWith(ApplicationParameters.PackageBackupLocation) || rollbackDirectory.is_equal_to(ApplicationParameters.PackageBackupLocation)) return;
+              
             FaultTolerance.try_catch_with_logging_exception(
                 () => _fileSystem.delete_directory_if_exists(rollbackDirectory, recursive: true),
                 "Attempted to remove '{0}' but had an error:".format_with(rollbackDirectory),