diff --git a/.gitattributes b/.gitattributes
index d7f9d36c50..2037909dbd 100644
--- a/.gitattributes
+++ b/.gitattributes
@@ -115,7 +115,6 @@
 *.wav filter=lfs diff=lfs merge=lfs -text
 *.webm filter=lfs diff=lfs merge=lfs -text
 *.wem filter=lfs diff=lfs merge=lfs -text
-*.wxs filter=lfs diff=lfs merge=lfs -text
 *.zip filter=lfs diff=lfs merge=lfs -text
 *.tbscene filter=lfs diff=lfs merge=lfs -text
 *.spp filter=lfs diff=lfs merge=lfs -text
diff --git a/cmake/Packaging.cmake b/cmake/Packaging.cmake
index 4f6565edc7..ba610b1883 100644
--- a/cmake/Packaging.cmake
+++ b/cmake/Packaging.cmake
@@ -13,7 +13,34 @@ if(NOT PAL_TRAIT_BUILD_CPACK_SUPPORTED)
     return()
 endif()
 
-ly_get_absolute_pal_filename(pal_dir ${CMAKE_SOURCE_DIR}/cmake/Platform/${PAL_HOST_PLATFORM_NAME})
+# public facing options will be used for conversion into cpack specific ones below.
+set(LY_INSTALLER_DOWNLOAD_URL "" CACHE STRING "URL embedded into the installer to download additional artifacts")
+set(LY_INSTALLER_LICENSE_URL "" CACHE STRING "Optionally embed a link to the license instead of raw text")
+
+# set all common cpack variable overrides first so they can be accessible via configure_file
+# when the platform specific settings are applied below.  additionally, any variable with
+# the "CPACK_" prefix will automatically be cached for use in any phase of cpack namely
+# pre/post build
+set(CPACK_PACKAGE_VENDOR "${PROJECT_NAME}")
+set(CPACK_PACKAGE_VERSION "${LY_VERSION_STRING}")
+set(CPACK_PACKAGE_DESCRIPTION_SUMMARY "Installation Tool")
+
+string(TOLOWER ${PROJECT_NAME} _project_name_lower)
+set(CPACK_PACKAGE_FILE_NAME "${_project_name_lower}_${LY_VERSION_STRING}_installer")
+
+set(DEFAULT_LICENSE_NAME "Apache-2.0")
+set(DEFAULT_LICENSE_FILE "${CMAKE_SOURCE_DIR}/LICENSE.txt")
+
+set(CPACK_RESOURCE_FILE_LICENSE ${DEFAULT_LICENSE_FILE})
+set(CPACK_LICENSE_URL ${LY_INSTALLER_LICENSE_URL})
+
+set(CPACK_PACKAGE_INSTALL_DIRECTORY "${CPACK_PACKAGE_VENDOR}/${CPACK_PACKAGE_VERSION}")
+
+# CMAKE_SOURCE_DIR doesn't equate to anything during execution of pre/post build scripts
+set(CPACK_SOURCE_DIR ${CMAKE_SOURCE_DIR}/cmake)
+
+# attempt to apply platform specific settings
+ly_get_absolute_pal_filename(pal_dir ${CPACK_SOURCE_DIR}/Platform/${PAL_HOST_PLATFORM_NAME})
 include(${pal_dir}/Packaging_${PAL_HOST_PLATFORM_NAME_LOWERCASE}.cmake)
 
 # if we get here and the generator hasn't been set, then a non fatal error occurred disabling packaging support
@@ -21,20 +48,6 @@ if(NOT CPACK_GENERATOR)
     return()
 endif()
 
-set(CPACK_PACKAGE_VENDOR "${PROJECT_NAME}")
-set(CPACK_PACKAGE_VERSION "${LY_VERSION_STRING}")
-set(CPACK_PACKAGE_DESCRIPTION_SUMMARY "Installation Tool")
-
-string(TOLOWER ${PROJECT_NAME} _project_name_lower)
-set(CPACK_PACKAGE_FILE_NAME "${_project_name_lower}_installer")
-
-set(DEFAULT_LICENSE_NAME "Apache-2.0")
-set(DEFAULT_LICENSE_FILE "${CMAKE_CURRENT_SOURCE_DIR}/LICENSE.txt")
-
-set(CPACK_RESOURCE_FILE_LICENSE ${DEFAULT_LICENSE_FILE})
-
-set(CPACK_PACKAGE_INSTALL_DIRECTORY "${CPACK_PACKAGE_VENDOR}/${CPACK_PACKAGE_VERSION}")
-
 # IMPORTANT: required to be included AFTER setting all property overrides
 include(CPack REQUIRED)
 
@@ -76,3 +89,12 @@ ly_configure_cpack_component(
     DISPLAY_NAME "${PROJECT_NAME} Core"
     DESCRIPTION "${PROJECT_NAME} Headers, Libraries and Tools"
 )
+
+if(LY_INSTALLER_DOWNLOAD_URL)
+    # this will set the following variables: CPACK_DOWNLOAD_SITE, CPACK_DOWNLOAD_ALL, and CPACK_UPLOAD_DIRECTORY
+    cpack_configure_downloads(
+        ${LY_INSTALLER_DOWNLOAD_URL}
+        UPLOAD_DIRECTORY ${CMAKE_BINARY_DIR}/_CPack_Uploads # to match the _CPack_Packages directory
+        ALL
+    )
+endif()
diff --git a/cmake/Platform/Windows/PackagingBootstrapper.wxs b/cmake/Platform/Windows/PackagingBootstrapper.wxs
new file mode 100644
index 0000000000..c3d1dd7a7b
--- /dev/null
+++ b/cmake/Platform/Windows/PackagingBootstrapper.wxs
@@ -0,0 +1,44 @@
+<?xml version="1.0" encoding="UTF-8"?>
+
+<?include "cpack_variables.wxi"?>
+
+<Wix xmlns="http://schemas.microsoft.com/wix/2006/wi"
+    xmlns:bal="http://schemas.microsoft.com/wix/BalExtension">
+
+    <Bundle Name="$(var.CPACK_PACKAGE_NAME) $(var.CPACK_PACKAGE_VERSION)"
+        Version="$(var.CPACK_PACKAGE_VERSION)"
+        Manufacturer="$(var.CPACK_PACKAGE_VENDOR)"
+        UpgradeCode="$(var.CPACK_BOOTSTRAP_UPGRADE_GUID)"
+        DisableModify="yes">
+
+        <Variable Name="InstallFolder"
+            Type="string"
+            Value="[ProgramFiles64Folder]$(var.CPACK_PACKAGE_INSTALL_DIRECTORY)"
+            bal:Overridable="yes"/>
+
+        <?ifdef CPACK_LICENSE_URL?>
+            <BootstrapperApplicationRef Id="WixStandardBootstrapperApplication.HyperlinkLicense">
+                <bal:WixStandardBootstrapperApplication
+                    LicenseUrl="$(var.CPACK_LICENSE_URL)"
+                    ShowVersion="yes" />
+            </BootstrapperApplicationRef>
+        <?else?>
+            <BootstrapperApplicationRef Id="WixStandardBootstrapperApplication.RtfLicense">
+                <bal:WixStandardBootstrapperApplication
+                    LicenseFile="$(var.CPACK_WIX_LICENSE_RTF)"
+                    ShowVersion="yes" />
+            </BootstrapperApplicationRef>
+        <?endif?>
+
+        <Chain>
+            <MsiPackage Id="$(var.CPACK_PACKAGE_FILE_NAME)"
+                SourceFile="$(var.CPACK_LOCAL_INSTALLER_DIR)/$(var.CPACK_PACKAGE_FILE_NAME).msi"
+                DownloadUrl="$(var.CPACK_DOWNLOAD_SITE)/{2}"
+                Vital="yes"
+                Compressed="no">
+
+                <MsiProperty Name="INSTALL_ROOT" Value="[InstallFolder]" />
+            </MsiPackage>
+        </Chain>
+    </Bundle>
+</Wix>
diff --git a/cmake/Platform/Windows/PackagingPostBuild.cmake b/cmake/Platform/Windows/PackagingPostBuild.cmake
new file mode 100644
index 0000000000..3ba6ef2096
--- /dev/null
+++ b/cmake/Platform/Windows/PackagingPostBuild.cmake
@@ -0,0 +1,88 @@
+#
+# All or portions of this file Copyright (c) Amazon.com, Inc. or its affiliates or
+# its licensors.
+#
+# For complete copyright and license terms please see the LICENSE at the root of this
+# distribution (the "License"). All use of this software is governed by the License,
+# or, if provided, by the license below or the license accompanying this file. Do not
+# remove or modify any license notices. This file is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+#
+
+# convert the path to a windows style path using string replace because TO_NATIVE_PATH
+# only works on real paths
+string(REPLACE "/" "\\" _fixed_package_install_dir ${CPACK_PACKAGE_INSTALL_DIRECTORY})
+
+# directory where the auto generated files live e.g <build>/_CPack_Package/win64/WIX
+set(_cpack_wix_out_dir ${CPACK_TOPLEVEL_DIRECTORY})
+set(_bootstrap_out_dir "${CPACK_TOPLEVEL_DIRECTORY}/bootstrap")
+
+set(_bootstrap_filename "${CPACK_PACKAGE_FILE_NAME}.exe")
+set(_bootstrap_output_file ${_cpack_wix_out_dir}/${_bootstrap_filename})
+
+set(_ext_flags
+    -ext WixBalExtension
+)
+
+set(_addtional_defines
+    -dCPACK_BOOTSTRAP_UPGRADE_GUID=${CPACK_WIX_BOOTSTRAP_UPGRADE_GUID}
+    -dCPACK_DOWNLOAD_SITE=${CPACK_DOWNLOAD_SITE}
+    -dCPACK_LOCAL_INSTALLER_DIR=${_cpack_wix_out_dir}
+    -dCPACK_PACKAGE_FILE_NAME=${CPACK_PACKAGE_FILE_NAME}
+    -dCPACK_PACKAGE_INSTALL_DIRECTORY=${_fixed_package_install_dir}
+)
+
+if(CPACK_LICENSE_URL)
+    list(APPEND _addtional_defines -dCPACK_LICENSE_URL=${CPACK_LICENSE_URL})
+endif()
+
+set(_candle_command
+    ${CPACK_WIX_CANDLE_EXECUTABLE}
+    -nologo
+    -arch x64
+    "-I${_cpack_wix_out_dir}" # to include cpack_variables.wxi
+    ${_addtional_defines}
+    ${_ext_flags}
+    "${CPACK_SOURCE_DIR}/Platform/Windows/PackagingBootstrapper.wxs"
+    -o "${_bootstrap_out_dir}/"
+)
+
+set(_light_command
+    ${CPACK_WIX_LIGHT_EXECUTABLE}
+    -nologo
+    ${_ext_flags}
+    ${_bootstrap_out_dir}/*.wixobj
+    -o "${_bootstrap_output_file}"
+)
+
+message(STATUS "Creating Bootstrap Installer...")
+execute_process(
+    COMMAND ${_candle_command}
+    COMMAND_ERROR_IS_FATAL ANY
+)
+execute_process(
+    COMMAND ${_light_command}
+    COMMAND_ERROR_IS_FATAL ANY
+)
+
+file(COPY ${_bootstrap_output_file}
+    DESTINATION ${CPACK_PACKAGE_DIRECTORY}
+)
+
+message(STATUS "Bootstrap installer generated to ${CPACK_PACKAGE_DIRECTORY}/${_bootstrap_filename}")
+
+# use the internal default path if somehow not specified from cpack_configure_downloads
+if(NOT CPACK_UPLOAD_DIRECTORY)
+    set(CPACK_UPLOAD_DIRECTORY ${CPACK_PACKAGE_DIRECTORY}/CPackUploads)
+endif()
+
+# copy the artifacts intended to be uploaded to a remote server into the folder specified
+# through cpack_configure_downloads.  this mimics the same process cpack does natively for
+# some other frameworks that have built-in online installer support.
+message(STATUS "Copying installer artifacts to upload directory...")
+file(REMOVE_RECURSE ${CPACK_UPLOAD_DIRECTORY})
+file(GLOB _artifacts "${_cpack_wix_out_dir}/*.msi" "${_cpack_wix_out_dir}/*.cab")
+file(COPY ${_artifacts}
+    DESTINATION ${CPACK_UPLOAD_DIRECTORY}
+)
+message(STATUS "Artifacts copied to ${CPACK_UPLOAD_DIRECTORY}")
diff --git a/cmake/Platform/Windows/PackagingTemplate.wxs.in b/cmake/Platform/Windows/PackagingTemplate.wxs.in
index 3e5db03ec2..0b3c597ab6 100644
--- a/cmake/Platform/Windows/PackagingTemplate.wxs.in
+++ b/cmake/Platform/Windows/PackagingTemplate.wxs.in
@@ -12,10 +12,10 @@
         Manufacturer="$(var.CPACK_PACKAGE_VENDOR)"
         UpgradeCode="$(var.CPACK_WIX_UPGRADE_GUID)">
 
-        <Package InstallerVersion="301" Compressed="yes"/>
+        <Package InstallerVersion="301" Compressed="yes" InstallPrivileges="elevated" InstallScope="perMachine"/>
 
-        <!-- auto distribute the installable files across N cab files and embed them in the final MSI -->
-        <MediaTemplate EmbedCab="yes"/>
+        <!-- auto distribute the installable files across N cab files -->
+        <MediaTemplate EmbedCab="$(var.CPACK_EMBED_ARTIFACTS)"/>
 
         <MajorUpgrade
             Schedule="afterInstallInitialize"
diff --git a/cmake/Platform/Windows/Packaging_windows.cmake b/cmake/Platform/Windows/Packaging_windows.cmake
index 8aa6f2386d..2ea35c1d9b 100644
--- a/cmake/Platform/Windows/Packaging_windows.cmake
+++ b/cmake/Platform/Windows/Packaging_windows.cmake
@@ -30,34 +30,23 @@ set(CPACK_GENERATOR "WIX")
 
 # CPack will generate the WiX product/upgrade GUIDs further down the chain if they weren't supplied
 # however, they are unique for each run.  instead, let's do the auto generation here and add it to
-# the cache for run persistence.  an additional cache file will be used to store the information on
-# the original generation so we still have the ability to detect if they are still being used.
-set(_guid_cache_file "${CMAKE_BINARY_DIR}/installer/wix_guid_cache.cmake")
-if(NOT EXISTS ${_guid_cache_file})
-    set(_wix_guid_namespace "6D43F57A-2917-4AD9-B758-1F13CDB08593")
+# the cache for run persistence and have the ability to detect if they are still being used.
+set(_wix_guid_namespace "6D43F57A-2917-4AD9-B758-1F13CDB08593")
 
-    # based the ISO-8601 standard (YYYY-MM-DDTHH-mm-ssTZD) e.g., 20210506145533
-    string(TIMESTAMP _guid_gen_timestamp "%Y%m%d%H%M%S")
-
-    file(WRITE ${_guid_cache_file} "set(_wix_guid_gen_timestamp ${_guid_gen_timestamp})\n")
-
-    string(UUID _default_product_guid
+function(generate_wix_guid out_value seed)
+    string(UUID _guid
         NAMESPACE ${_wix_guid_namespace}
-        NAME "ProductID_${_guid_gen_timestamp}"
+        NAME ${seed}
         TYPE SHA1
         UPPER
     )
-    file(APPEND ${_guid_cache_file} "set(_wix_default_product_guid ${_default_product_guid})\n")
 
-    string(UUID _default_upgrade_guid
-        NAMESPACE ${_wix_guid_namespace}
-        NAME "UpgradeCode_${_guid_gen_timestamp}"
-        TYPE SHA1
-        UPPER
-    )
-    file(APPEND ${_guid_cache_file} "set(_wix_default_upgrade_guid ${_default_upgrade_guid})\n")
-endif()
-include(${_guid_cache_file})
+    set(${out_value} ${_guid} PARENT_SCOPE)
+endfunction()
+
+set(_guid_seed_base "${PROJECT_NAME}_${LY_VERSION_STRING}")
+generate_wix_guid(_wix_default_product_guid "${_guid_seed_base}_ProductID" )
+generate_wix_guid(_wix_default_upgrade_guid "${_guid_seed_base}_UpgradeCode")
 
 set(LY_WIX_PRODUCT_GUID "${_wix_default_product_guid}" CACHE STRING "GUID for the Product ID field. Format: XXXXXXXX-XXXX-XXXX-XXXX-XXXXXXXXXXXX")
 set(LY_WIX_UPGRADE_GUID "${_wix_default_upgrade_guid}" CACHE STRING "GUID for the Upgrade Code field. Format: XXXXXXXX-XXXX-XXXX-XXXX-XXXXXXXXXXXX")
@@ -89,4 +78,21 @@ endif()
 set(CPACK_WIX_PRODUCT_GUID ${LY_WIX_PRODUCT_GUID})
 set(CPACK_WIX_UPGRADE_GUID ${LY_WIX_UPGRADE_GUID})
 
-set(CPACK_WIX_TEMPLATE "${CMAKE_SOURCE_DIR}/cmake/Platform/Windows/PackagingTemplate.wxs.in")
+set(CPACK_WIX_TEMPLATE "${CPACK_SOURCE_DIR}/Platform/Windows/PackagingTemplate.wxs.in")
+
+set(_embed_artifacts "yes")
+
+if(LY_INSTALLER_DOWNLOAD_URL)
+    set(_embed_artifacts "no")
+
+    # the bootstrapper will at the very least need a different upgrade guid
+    generate_wix_guid(CPACK_WIX_BOOTSTRAP_UPGRADE_GUID "${_guid_seed_base}_Bootstrap_UpgradeCode")
+
+    set(CPACK_POST_BUILD_SCRIPTS
+        ${CPACK_SOURCE_DIR}/Platform/Windows/PackagingPostBuild.cmake
+    )
+endif()
+
+set(CPACK_WIX_CANDLE_EXTRA_FLAGS
+    -dCPACK_EMBED_ARTIFACTS=${_embed_artifacts}
+)
diff --git a/cmake/Platform/Windows/platform_windows_files.cmake b/cmake/Platform/Windows/platform_windows_files.cmake
index 2fc869b43e..84d1a3098c 100644
--- a/cmake/Platform/Windows/platform_windows_files.cmake
+++ b/cmake/Platform/Windows/platform_windows_files.cmake
@@ -24,5 +24,7 @@ set(FILES
     PALDetection_windows.cmake
     Install_windows.cmake
     Packaging_windows.cmake
+    PackagingBootstrapper.wxs
+    PackagingPostBuild.cmake
     PackagingTemplate.wxs.in
 )