diff --git a/src/NuGetGallery/Services/PackageService.cs b/src/NuGetGallery/Services/PackageService.cs
index 6c412e802b..7cc99dd241 100644
--- a/src/NuGetGallery/Services/PackageService.cs
+++ b/src/NuGetGallery/Services/PackageService.cs
@@ -793,7 +793,7 @@ public async Task UpdateIsLatestAsync(PackageRegistration packageRegistration, b
 
             // TODO: improve setting the latest bit; this is horrible. Trigger maybe?
             var currentUtcTime = DateTime.UtcNow;
-            foreach (var pv in packageRegistration.Packages.Where(p => p.IsLatest || p.IsLatestStable))
+            foreach (var pv in packageRegistration.Packages.Where(p => p.IsLatest || p.IsLatestStable || p.IsLatestSemVer2 || p.IsLatestStableSemVer2))
             {
                 pv.IsLatest = false;
                 pv.IsLatestStable = false;
diff --git a/tests/NuGetGallery.Facts/Services/PackageServiceFacts.cs b/tests/NuGetGallery.Facts/Services/PackageServiceFacts.cs
index 547a839d78..dc535e30a5 100644
--- a/tests/NuGetGallery.Facts/Services/PackageServiceFacts.cs
+++ b/tests/NuGetGallery.Facts/Services/PackageServiceFacts.cs
@@ -1052,6 +1052,50 @@ public async Task CommitIfCommitChangesIsTrue()
                 packageRepository.Verify(r => r.CommitChangesAsync(), Times.Once());
             }
 
+            [Fact]
+            public async Task ResetsCurrentLatestPackageVersionsBeforeUpdate()
+            {
+                // Arrange
+                var packageRegistration = new PackageRegistration();
+
+                var previousLatestStable = new Package { PackageRegistration = packageRegistration, Version = "1.0.0", IsLatestStable = true };
+                packageRegistration.Packages.Add(previousLatestStable);
+                var previousLatest = new Package { PackageRegistration = packageRegistration, Version = "1.0.0-alpha", IsLatest = true, IsPrerelease = true };
+                packageRegistration.Packages.Add(previousLatest);
+                var previousLatestStableSemVer2 = new Package { PackageRegistration = packageRegistration, Version = "1.0.1+metadata", IsLatestStableSemVer2 = true, SemVerLevelKey = SemVerLevelKey.SemVer2 };
+                packageRegistration.Packages.Add(previousLatestStableSemVer2);
+                var previousLatestSemVer2 = new Package { PackageRegistration = packageRegistration, Version = "1.0.1-alpha.1", IsLatestSemVer2 = true, IsPrerelease = true, SemVerLevelKey = SemVerLevelKey.SemVer2 };
+                packageRegistration.Packages.Add(previousLatestSemVer2);
+
+                // Simulates adding newer versions, to ensure the previous latest are no longer latest at end of test.
+                var newLatestStable = new Package { PackageRegistration = packageRegistration, Version = "1.0.1", IsLatestStable = true };
+                packageRegistration.Packages.Add(newLatestStable);
+                var newLatest = new Package { PackageRegistration = packageRegistration, Version = "1.0.2-alpha", IsLatest = true, IsPrerelease = true };
+                packageRegistration.Packages.Add(newLatest);
+                var newLatestStableSemVer2 = new Package { PackageRegistration = packageRegistration, Version = "1.0.2+metadata", IsLatestStableSemVer2 = true, SemVerLevelKey = SemVerLevelKey.SemVer2 };
+                packageRegistration.Packages.Add(newLatestStableSemVer2);
+                var newLatestSemVer2 = new Package { PackageRegistration = packageRegistration, Version = "1.0.3-alpha.1", IsLatestSemVer2 = true, IsPrerelease = true, SemVerLevelKey = SemVerLevelKey.SemVer2 };
+                packageRegistration.Packages.Add(newLatestSemVer2);
+
+                var packageRepository = new Mock<IEntityRepository<Package>>();
+
+                var service = CreateService(packageRepository: packageRepository);
+
+                // Act
+                await service.UpdateIsLatestAsync(packageRegistration, commitChanges: true);
+
+                // Assert
+                Assert.False(previousLatestStable.IsLatestStable);
+                Assert.False(previousLatest.IsLatest);
+                Assert.False(previousLatestSemVer2.IsLatestSemVer2);
+                Assert.False(previousLatestStableSemVer2.IsLatestStableSemVer2);
+                
+                Assert.True(newLatestStable.IsLatestStable);
+                Assert.True(newLatest.IsLatest);
+                Assert.True(newLatestSemVer2.IsLatestSemVer2);
+                Assert.True(newLatestStableSemVer2.IsLatestStableSemVer2);
+            }
+
             [Fact]
             public async Task UpdateIsLatestScenarioForPrereleaseAsAbsoluteLatest()
             {