diff --git a/src/chocolatey/infrastructure.app/services/NugetService.cs b/src/chocolatey/infrastructure.app/services/NugetService.cs
index a872b06515..e0dd2c9456 100644
--- a/src/chocolatey/infrastructure.app/services/NugetService.cs
+++ b/src/chocolatey/infrastructure.app/services/NugetService.cs
@@ -862,8 +862,19 @@ public ConcurrentDictionary<string, PackageResult> get_outdated(ChocolateyConfig
 
 			foreach (var packageName in packageNames)
 			{
-				// LastOrDefault to get the latest package from local repository, because all packages have set IsLatestVersion to true
-				var latestPackage = packageManager.SourceRepository.GetPackages().Where(x => x.Id.ToLower() == packageName && x.IsLatestVersion).LastOrDefault();
+				// If using local repository as source all packages have set IsLatestVersion to true.
+				var latestPackages = packageManager.SourceRepository.GetPackages().Where(x => x.Id.ToLower() == packageName && x.IsLatestVersion).ToList();
+
+				IPackage latestPackage = null;
+
+				if(latestPackages.Count > 1)
+				{
+					latestPackage = latestPackages.Last();
+				}
+				else
+				{
+					latestPackage = latestPackages.FirstOrDefault();
+				}
 
 				if(latestPackage == null)
 				{