diff --git a/src/WingetCreateCLI/Commands/NewCommand.cs b/src/WingetCreateCLI/Commands/NewCommand.cs
index b3e9f437..d8ed5578 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)
@@ -449,22 +457,51 @@ private static void PromptForPortableAliasIfApplicable(Installer installer)
 
                 if (!string.IsNullOrEmpty(portableCommandAlias))
                 {
-                    List<string> portableCommands = new List<string> { portableCommandAlias };
+                    List<string> portableCommands = new List<string> { portableCommandAlias.Trim() };
                     installer.Commands = portableCommands;
                 }
             }
 
             if (installer.NestedInstallerType == NestedInstallerType.Portable)
             {
-                foreach (NestedInstallerFile nestedInstallerFile in installer.NestedInstallerFiles)
+                string portableCommandAlias = Prompt.Input<string>(Resources.PortableCommandAlias_Message);
+
+                if (!string.IsNullOrEmpty(portableCommandAlias))
                 {
-                    string portableCommandAlias = Prompt.Input<string>(Resources.PortableCommandAlias_Message);
+                    installer.NestedInstallerFiles.First().PortableCommandAlias = portableCommandAlias.Trim();
+                }
+            }
+        }
 
-                    if (!string.IsNullOrEmpty(portableCommandAlias))
-                    {
-                        nestedInstallerFile.PortableCommandAlias = portableCommandAlias;
-                    }
+        /// <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 nestedPortableInstallers = installerManifest.Installers.Where(i => i.NestedInstallerType == NestedInstallerType.Portable).ToList();
+            var mergeableInstallersList = nestedPortableInstallers.GroupBy(i => i.Architecture + i.InstallerSha256).ToList();
+            foreach (var 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);
             }
         }
 
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>