diff --git a/src/AppInstallerCLICore/Workflows/InstallFlow.cpp b/src/AppInstallerCLICore/Workflows/InstallFlow.cpp
index 8f6b17964a..b6ca2db78a 100644
--- a/src/AppInstallerCLICore/Workflows/InstallFlow.cpp
+++ b/src/AppInstallerCLICore/Workflows/InstallFlow.cpp
@@ -641,17 +641,14 @@ namespace AppInstaller::CLI::Workflow
         }
 
         // Report dependencies
-        DependencyList allDependencies;
-        for (auto package : context.Get<Execution::Data::PackagesToInstall>())
+        if (Settings::ExperimentalFeature::IsEnabled(Settings::ExperimentalFeature::Feature::Dependencies))
         {
-            if (Settings::ExperimentalFeature::IsEnabled(Settings::ExperimentalFeature::Feature::Dependencies))
+            DependencyList allDependencies;
+            for (auto package : context.Get<Execution::Data::PackagesToInstall>())
             {
                 allDependencies.Add(package.Installer.Dependencies);
             }
-        }
 
-        if (Settings::ExperimentalFeature::IsEnabled(Settings::ExperimentalFeature::Feature::Dependencies))
-        {
             context.Add<Execution::Data::Dependencies>(allDependencies);
             context << Workflow::ReportDependencies(m_dependenciesReportMessage);
         }
diff --git a/src/AppInstallerCLICore/Workflows/WorkflowBase.h b/src/AppInstallerCLICore/Workflows/WorkflowBase.h
index 2a7a976964..a78170f27d 100644
--- a/src/AppInstallerCLICore/Workflows/WorkflowBase.h
+++ b/src/AppInstallerCLICore/Workflows/WorkflowBase.h
@@ -194,7 +194,7 @@ namespace AppInstaller::CLI::Workflow
     // Ensures that there is only one result in the search.
     // Required Args: bool indicating if the search result is from installed source
     // Inputs: SearchResult
-    // Outputs: None
+    // Outputs: Package
     struct EnsureOneMatchFromSearchResult : public WorkflowTask
     {
         EnsureOneMatchFromSearchResult(bool isFromInstalledSource) :
diff --git a/src/AppInstallerRepositoryCore/CompositeSource.cpp b/src/AppInstallerRepositoryCore/CompositeSource.cpp
index 21ec7c1a9a..35412d39b8 100644
--- a/src/AppInstallerRepositoryCore/CompositeSource.cpp
+++ b/src/AppInstallerRepositoryCore/CompositeSource.cpp
@@ -553,14 +553,42 @@ namespace AppInstaller::Repository
 
                     SearchResult installedCrossRef = m_installedSource->Search(systemReferenceSearch);
 
-                    for (auto&& crossRef : installedCrossRef.Matches)
+                    std::shared_ptr<IPackage> installedPackage;
+                    if (installedCrossRef.Matches.size() == 1)
                     {
-                        if (!result.ContainsInstalledPackage(crossRef.Package.get()))
+                        installedPackage = std::move(installedCrossRef.Matches[0].Package);
+                    }
+                    else if (installedCrossRef.Matches.size() > 1)
+                    {
+                        AICLI_LOG(Repo, Info,
+                            << "Found multiple matches for available package [" << match.Package->GetProperty(PackageProperty::Id) <<
+                            "] in source [" << source->GetIdentifier() << "] when searching for [" << systemReferenceSearch.ToString() << "]");
+
+                        // More than one match found for the system reference; run some heuristics to check for a match
+                        for (auto&& crossRef : installedCrossRef.Matches)
                         {
-                            foundInstalledMatch = true;
-                            result.Matches.emplace_back(std::make_shared<CompositePackage>(std::move(crossRef.Package), std::move(match.Package)), match.MatchCriteria);
+                            AICLI_LOG(Repo, Info, << "  Checking match with package id: " << crossRef.Package->GetProperty(PackageProperty::Id));
+                            if (IsStrongMatchField(crossRef.MatchCriteria.Field))
+                            {
+                                if (!installedPackage)
+                                {
+                                    installedPackage = std::move(crossRef.Package);
+                                }
+                                else
+                                {
+                                    AICLI_LOG(Repo, Info, << "  Found multiple packages with strong match fields");
+                                    installedPackage.reset();
+                                    break;
+                                }
+                            }
                         }
                     }
+
+                    if (installedPackage && !result.ContainsInstalledPackage(installedPackage.get()))
+                    {
+                        foundInstalledMatch = true;
+                        result.Matches.emplace_back(std::make_shared<CompositePackage>(std::move(installedPackage), std::move(match.Package)), match.MatchCriteria);
+                    }
                 }
 
                 // If there was no correlation for this package, add it without one.