diff --git a/src/AppInstallerCLICore/Workflows/DependencyNodeProcessor.cpp b/src/AppInstallerCLICore/Workflows/DependencyNodeProcessor.cpp
index ad24e298f5..166eb401b9 100644
--- a/src/AppInstallerCLICore/Workflows/DependencyNodeProcessor.cpp
+++ b/src/AppInstallerCLICore/Workflows/DependencyNodeProcessor.cpp
@@ -45,20 +45,7 @@ namespace AppInstaller::CLI::Workflow
         m_nodePackageInstalledVersion = GetInstalledVersion(package);
         std::shared_ptr<IPackageVersionCollection> availableVersions = GetAvailableVersionsForInstalledVersion(package);
 
-        if (m_context.Args.Contains(Execution::Args::Type::Force))
-        {
-            m_nodePackageLatestVersion = availableVersions->GetLatestVersion();
-        }
-        else
-        {
-            Pinning::PinBehavior pinBehavior = m_context.Args.Contains(Execution::Args::Type::IncludePinned) ? Pinning::PinBehavior::IncludePinned : Pinning::PinBehavior::ConsiderPins;
-
-            Pinning::PinningData pinningData{ Pinning::PinningData::Disposition::ReadOnly };
-            auto evaluator = pinningData.CreatePinStateEvaluator(pinBehavior, m_nodePackageInstalledVersion);
-
-            m_nodePackageLatestVersion = evaluator.GetLatestAvailableVersionForPins(availableVersions);
-        }
-
+        // If the package is already installed and meets the dependency's MinVersion, skip.
         if (m_nodePackageInstalledVersion && dependencyNode.IsVersionOk(Utility::Version(m_nodePackageInstalledVersion->GetProperty(PackageVersionProperty::Version))))
         {
             // return empty dependency list,
@@ -66,50 +53,97 @@ namespace AppInstaller::CLI::Workflow
             return DependencyNodeProcessorResult::Skipped;
         }
 
-        if (!m_nodePackageLatestVersion)
+        if (!availableVersions)
         {
             error << Resource::String::DependenciesFlowPackageVersionNotFound(Utility::LocIndView{ Utility::Normalize(packageId) }) << std::endl;
-            AICLI_LOG(CLI, Error, << "Latest available version not found for package " << packageId);
+            AICLI_LOG(CLI, Error, << "Available versions not found for package " << packageId);
             return DependencyNodeProcessorResult::Error;
         }
 
-        if (!dependencyNode.IsVersionOk(Utility::Version(m_nodePackageLatestVersion->GetProperty(PackageVersionProperty::Version))))
-        {
-            error << Resource::String::DependenciesFlowNoMinVersion(Utility::LocIndView{ Utility::Normalize(packageId) }) << std::endl;
-            AICLI_LOG(CLI, Error, << "No suitable min version found for package " << packageId);
-            return DependencyNodeProcessorResult::Error;
-        }
-
-        m_nodeManifest = m_nodePackageLatestVersion->GetManifest();
-        m_nodeManifest.ApplyLocale();
+        // Determine pin behavior: --force should ignore pin restrictions for selection purposes.
+        Pinning::PinBehavior pinBehavior = m_context.Args.Contains(Execution::Args::Type::IncludePinned) || m_context.Args.Contains(Execution::Args::Type::Force)
+            ? Pinning::PinBehavior::IncludePinned
+            : Pinning::PinBehavior::ConsiderPins;
 
-        if (m_nodeManifest.Installers.empty())
-        {
-            error << Resource::String::DependenciesFlowNoInstallerFound(Utility::LocIndView{ Utility::Normalize(m_nodeManifest.Id) }) << std::endl;
-            AICLI_LOG(CLI, Error, << "Installer not found for manifest " << m_nodeManifest.Id << " with version" << m_nodeManifest.Version);
-            return DependencyNodeProcessorResult::Error;
-        }
+        Pinning::PinningData pinningData{ Pinning::PinningData::Disposition::ReadOnly };
+        auto evaluator = pinningData.CreatePinStateEvaluator(pinBehavior, m_nodePackageInstalledVersion);
 
+        // Iterate versions from newest to oldest, looking for the first version that:
+        //  - satisfies dependency.MinVersion
+        //  - is not pinned (unless includePinned or force)
+        //  - has at least one applicable installer according to ManifestComparator
+        bool foundCandidate = false;
         IPackageVersion::Metadata installationMetadata;
         if (m_nodePackageInstalledVersion)
         {
             installationMetadata = m_nodePackageInstalledVersion->GetMetadata();
         }
 
-        ManifestComparator manifestComparator(GetManifestComparatorOptions(m_context, installationMetadata));
-        auto [installer, inapplicabilities] = manifestComparator.GetPreferredInstaller(m_nodeManifest);
+        Manifest::ManifestComparator manifestComparator(GetManifestComparatorOptions(m_context, installationMetadata));
+
+        auto versionKeys = availableVersions->GetVersionKeys();
+        for (const auto& key : versionKeys)
+        {
+            auto candidateVersion = availableVersions->GetVersion(key);
+            if (!candidateVersion)
+            {
+                continue;
+            }
+
+            // Skip pinned versions unless explicitly allowed by flags
+            auto pinType = evaluator.EvaluatePinType(candidateVersion);
+            if (pinType != Pinning::PinType::Unknown && !m_context.Args.Contains(Execution::Args::Type::IncludePinned) && !m_context.Args.Contains(Execution::Args::Type::Force))
+            {
+                // This version is pinned and the user did not request to include pinned versions
+                AICLI_LOG(CLI, Info, << "Skipping pinned version " << candidateVersion->GetProperty(PackageVersionProperty::Version) << " for package " << packageId);
+                continue;
+            }
+
+            // Check MinVersion constraint from the dependency node
+            Utility::Version candidateVer(candidateVersion->GetProperty(PackageVersionProperty::Version));
+            if (!dependencyNode.IsVersionOk(candidateVer))
+            {
+                // Candidate version is lower than required min version for this dependency
+                AICLI_LOG(CLI, Info, << "Skipping version " << candidateVer.ToString() << " because it does not meet MinVersion for dependency " << dependencyNode.Id());
+                continue;
+            }
+
+            // Load manifest for this version and attempt installer selection
+            Manifest::Manifest manifest = candidateVersion->GetManifest();
+            manifest.ApplyLocale();
+
+            if (manifest.Installers.empty())
+            {
+                AICLI_LOG(CLI, Info, << "No installers in manifest for " << manifest.Id << " version " << manifest.Version);
+                continue;
+            }
+
+            auto [installer, inapplicabilities] = manifestComparator.GetPreferredInstaller(manifest);
+
+            if (!installer.has_value())
+            {
+                // No suitable installer for this manifest; keep searching older versions.
+                AICLI_LOG(CLI, Info, << "No suitable installer found for manifest " << manifest.Id << " version " << manifest.Version);
+                continue;
+            }
+
+            // Found a working candidate
+            m_nodePackageLatestVersion = candidateVersion;
+            m_nodeManifest = std::move(manifest);
+            m_installer = installer.value();
+            foundCandidate = true;
+            break;
+        }
 
-        if (!installer.has_value())
+        if (!foundCandidate)
         {
-            auto manifestId = Utility::LocIndString{ Utility::Normalize(m_nodeManifest.Id) };
-            auto manifestVersion = Utility::LocIndString{ m_nodeManifest.Version };
-            error << Resource::String::DependenciesFlowNoSuitableInstallerFound(manifestId, manifestVersion) << std::endl;
-            AICLI_LOG(CLI, Error, << "No suitable installer found for manifest " << m_nodeManifest.Id << " with version " << m_nodeManifest.Version);
+            error << Resource::String::DependenciesFlowNoSuitableInstallerFound(Utility::LocIndView{ Utility::Normalize(packageId) }, Utility::LocIndView{ Utility::LocIndString{ /* empty version to indicate search failed across versions */ "" } }) << std::endl;
+            AICLI_LOG(CLI, Error, << "No suitable installer found for any available version of package " << packageId);
             return DependencyNodeProcessorResult::Error;
         }
 
-        m_installer = installer.value();
+        // Extract the dependency list from the chosen installer's dependencies
         m_dependenciesList = m_installer.Dependencies;
         return DependencyNodeProcessorResult::Success;
     }
-}
+}
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