diff --git a/src/code/UpdatePSResource.cs b/src/code/UpdatePSResource.cs
index fcb0dfe3e..86b66dc71 100644
--- a/src/code/UpdatePSResource.cs
+++ b/src/code/UpdatePSResource.cs
@@ -354,14 +354,22 @@ private string[] ProcessPackageNames(
                     continue;
                 }
 
-                if ((versionRange == VersionRange.All && repositoryPackage.Version > installedPackage.Version) ||
+                if (!NuGetVersion.TryParse(repositoryPackage.Version.ToString(), out NuGetVersion repositoryPackageNuGetVersion))
+                {
+                    WriteWarning($"Cannot parse nuget version in repository package '{repositoryPackage.Name}'. Cannot update package.");
+                    continue;
+                }
+
+                // We compare NuGetVersions instead of System.Version as repositoryPackage.Version (3.0.17.0) and installedPackage.Version (3.0.17.-1)
+                // should refer to the same version but with System.Version end up having discrepancies which yields incorrect results.
+                if ((versionRange == VersionRange.All && repositoryPackageNuGetVersion > installedVersion) ||
                     !versionRange.Satisfies(installedVersion))
                 {
                     namesToUpdate.Add(repositoryPackage.Name);
                 }
                 else
                 {
-                    WriteVerbose($"Installed package {repositoryPackage.Name} is up to date.");
+                    WriteVerbose($"Installed package {repositoryPackage.Name} {repositoryPackageNuGetVersion} is already up to date.");
                 }
             }