diff --git a/src/WingetCreateCLI/Commands/NewCommand.cs b/src/WingetCreateCLI/Commands/NewCommand.cs
index b3e9f437..badbe943 100644
--- a/src/WingetCreateCLI/Commands/NewCommand.cs
+++ b/src/WingetCreateCLI/Commands/NewCommand.cs
@@ -172,15 +172,18 @@ public override async Task<bool> Execute()
                             selectedInstallers = Prompt.MultiSelect(Resources.SelectInstallersFromZip_Message, extractedFiles, minimum: 1).ToList();
                         }
 
-                        installerUpdateList.Add(
+                        foreach (var installer in selectedInstallers)
+                        {
+                            installerUpdateList.Add(
                             new InstallerMetadata
                             {
                                 InstallerUrl = installerUrl,
                                 PackageFile = packageFile,
-                                RelativeFilePaths = selectedInstallers,
+                                RelativeFilePaths = new List<string> { installer },
                                 IsZipFile = true,
                                 ExtractedDirectory = extractDirectory,
                             });
+                        }
                     }
                     else
                     {
@@ -270,6 +273,7 @@ private static void PromptPropertiesAndDisplayManifests(Manifests manifests)
             PromptRequiredProperties(manifests.VersionManifest);
             PromptRequiredProperties(manifests.InstallerManifest, manifests.VersionManifest);
             PromptRequiredProperties(manifests.DefaultLocaleManifest, manifests.VersionManifest);
+            MergeNestedInstallerFilesIfApplicable(manifests.InstallerManifest);
 
             Console.WriteLine();
             if (Prompt.Confirm(Resources.ModifyOptionalDefaultLocaleFields_Message))
@@ -359,6 +363,12 @@ private static void PromptInstallerProperties<T>(T manifest, PropertyInfo proper
             List<Installer> installers = new List<Installer>((ICollection<Installer>)property.GetValue(manifest));
             foreach (var installer in installers)
             {
+                Console.WriteLine();
+                if (installer.InstallerType == InstallerType.Zip)
+                {
+                    Logger.InfoLocalized(nameof(Resources.NestedInstallerParsing_HelpText), installer.NestedInstallerFiles.First().RelativeFilePath, installer.InstallerUrl);
+                }
+
                 var installerProperties = installer.GetType().GetProperties().ToList();
 
                 var requiredInstallerProperties = installerProperties
@@ -369,8 +379,6 @@ private static void PromptInstallerProperties<T>(T manifest, PropertyInfo proper
                 // If the installerType is EXE, prompt the user for whether the package is a portable
                 if (installer.InstallerType == InstallerType.Exe || installer.NestedInstallerType == NestedInstallerType.Exe)
                 {
-                    Console.WriteLine();
-
                     if (!PromptForPortableExe(installer))
                     {
                         // If we know the installertype is EXE, prompt the user for installer switches (silent and silentwithprogress)
@@ -468,6 +476,69 @@ private static void PromptForPortableAliasIfApplicable(Installer installer)
             }
         }
 
+        /// <summary>
+        /// Retrieve nested portable installers that are compatible to have their NestedInstallerFiles merged.
+        /// </summary>
+        /// <returns>A list of lists where each list element contains installers that are applicable for merge.</returns>
+        private static List<List<Installer>> GetNestedPortableInstallersForMerge(InstallerManifest installerManifest)
+        {
+            List<List<Installer>> nestedPortablesCompatibleForMerge = new List<List<Installer>>();
+
+            foreach (Installer installer in installerManifest.Installers)
+            {
+                if (installer.NestedInstallerType == NestedInstallerType.Portable)
+                {
+                    // If the current installer has the same hash and architecture as another installer, add it to an existing list
+                    // else create a new list
+                    var matchingInstallers = nestedPortablesCompatibleForMerge.SingleOrDefault(i => i.Any(x =>
+                    x.Architecture.Equals(installer.Architecture) &&
+                    x.InstallerSha256.Equals(installer.InstallerSha256)));
+
+                    if (matchingInstallers != null)
+                    {
+                        matchingInstallers.Add(installer);
+                    }
+                    else
+                    {
+                        nestedPortablesCompatibleForMerge.Add(new List<Installer> { installer });
+                    }
+                }
+            }
+
+            return nestedPortablesCompatibleForMerge;
+        }
+
+        /// <summary>
+        /// Merge nested installer files into a single installer if:
+        /// 1. Matching installers have NestedInstallerType: portable.
+        /// 2. Matching installers have the same architecture.
+        /// 3. Matching installers have the same hash.
+        /// </summary>
+        private static void MergeNestedInstallerFilesIfApplicable(InstallerManifest installerManifest)
+        {
+            var mergeableInstallersList = GetNestedPortableInstallersForMerge(installerManifest);
+            foreach (List<Installer> installers in mergeableInstallersList)
+            {
+                // First installer in each list is used to merge into
+                var installerToMergeInto = installers.First();
+
+                // Remove the first installer from the manifest, will be added back once the merge is complete
+                installerManifest.Installers.Remove(installerToMergeInto);
+
+                var installersToMerge = installers.Skip(1).ToList();
+
+                // Append NestedInstallerFiles of other matching installers and remove them from the manifest
+                foreach (var installer in installersToMerge)
+                {
+                    installerToMergeInto.NestedInstallerFiles.AddRange(installer.NestedInstallerFiles);
+                    installerManifest.Installers.Remove(installer);
+                }
+
+                // Add the installer with the merged nested installer files back to the manifest
+                installerManifest.Installers.Add(installerToMergeInto);
+            }
+        }
+
         /// <summary>
         /// Prompts for the package identifier and applies the value to all manifests.
         /// </summary>
diff --git a/src/WingetCreateCLI/Properties/Resources.Designer.cs b/src/WingetCreateCLI/Properties/Resources.Designer.cs
index 13c42e75..5a45cd10 100644
--- a/src/WingetCreateCLI/Properties/Resources.Designer.cs
+++ b/src/WingetCreateCLI/Properties/Resources.Designer.cs
@@ -1472,6 +1472,17 @@ public static string Name_KeywordDescription {
                 return ResourceManager.GetString("Name_KeywordDescription", resourceCulture);
             }
         }
+
+        /// <summary>
+        ///   Looks up a localized string similar to Parsing nested installer &apos;{0}&apos; from {1}.
+        /// </summary>
+        public static string NestedInstallerParsing_HelpText
+        {
+            get
+            {
+                return ResourceManager.GetString("NestedInstallerParsing_HelpText", resourceCulture);
+            }
+        }
         
         /// <summary>
         ///   Looks up a localized string similar to Nested installer not found in zip archive: {0}.
diff --git a/src/WingetCreateCLI/Properties/Resources.resx b/src/WingetCreateCLI/Properties/Resources.resx
index c75e4ac4..85cc85d5 100644
--- a/src/WingetCreateCLI/Properties/Resources.resx
+++ b/src/WingetCreateCLI/Properties/Resources.resx
@@ -958,6 +958,11 @@
   <data name="InvocationParameter_KeywordDescription" xml:space="preserve">
     <value>The optional parameter for invocable files</value>
   </data>
+  <data name="NestedInstallerParsing_HelpText" xml:space="preserve">
+    <value>Parsing nested installer '{0}' from {1}</value>
+    <comment>{0} - will be replaced with RelativeFilePath of the nested installer
+    {1} - will be replaced by the InstallerUrl</comment>
+  </data>
   <data name="NestedInstallerFileNotFound_Error" xml:space="preserve">
     <value>Nested installer not found in zip archive: {0}</value>
     <comment>{0} - represents the relative file path of the nested installer file.</comment>