diff --git a/src/jdk.jpackage/share/classes/jdk/jpackage/internal/resources/HelpResources.properties b/src/jdk.jpackage/share/classes/jdk/jpackage/internal/resources/HelpResources.properties
index 0b2ca83a7d7..7f570e71330 100644
--- a/src/jdk.jpackage/share/classes/jdk/jpackage/internal/resources/HelpResources.properties
+++ b/src/jdk.jpackage/share/classes/jdk/jpackage/internal/resources/HelpResources.properties
@@ -405,20 +405,24 @@ help.option.win-help-url=\
 \          URL where user can obtain further information or technical support
 
 help.option.win-menu=\
-\          Request to add a Start menu shortcut for this application
+\          Adds a Start menu shortcut for this application, or requests\n\
+\          to do so if --win-shortcut-prompt is specified
 
 help.option.win-menu-group=\
 \          Start Menu group this application is placed in
 
 help.option.win-per-user-install=\
-\          Request to perform an install on a per-user basis
+\          Installs the application on a per-user basis.\n\
+\          Without this option installs per-machine
 
 help.option.win-shortcut=\
-\          Request to add desktop shortcut for this application
+\          Adds a desktop shortcut for this application, or requests\n\
+\          to do so if --win-shortcut-prompt is specified
 
 help.option.win-shortcut-prompt=\
-\          Adds a dialog to enable the user to choose if shortcuts\n\
-\          will be created by installer.
+\          Adds a dialog if at least one of --win-menu or --win-shortcut\n\
+\          are specified to enable the user to choose if these shortcuts\n\
+\          will be created by the installer
 
 help.option.win-update-url=\
 \          URL of available application update information
diff --git a/src/jdk.jpackage/share/man/jpackage.md b/src/jdk.jpackage/share/man/jpackage.md
index 9ba5949866f..156b05307b7 100644
--- a/src/jdk.jpackage/share/man/jpackage.md
+++ b/src/jdk.jpackage/share/man/jpackage.md
@@ -410,7 +410,8 @@ The `jpackage` tool will take as input a Java application and a Java run-time im
 
 <a id="option-win-menu">`--win-menu`</a>
 
-:   Request to add a Start Menu shortcut for this application
+:   Adds a Start menu shortcut for this application, or requests to do so
+    if --win-shortcut-prompt is specified
 
 <a id="option-win-menu-group">`--win-menu-group` *menu-group-name*</a>
 
@@ -418,15 +419,17 @@ The `jpackage` tool will take as input a Java application and a Java run-time im
 
 <a id="option-win-per-user-install">`--win-per-user-install`</a>
 
-:   Request to perform an install on a per-user basis
+:   Installs the application on a per-user basis. Without this option installs per-machine
 
 <a id="option-win-shortcut">`--win-shortcut`</a>
 
-:   Request to create a desktop shortcut for this application
+:   Adds a desktop shortcut for this application, or requests to do so
+    if --win-shortcut-prompt is specified
 
 <a id="option-win-shortcut-prompt">`--win-shortcut-prompt`</a>
 
-:   Adds a dialog to enable the user to choose if shortcuts will be created by installer
+:   Adds a dialog if at least one of --win-menu or --win-shortcut are specified
+    to enable the user to choose if these shortcuts will be created by the installer
 
 <a id="option-win-update-url">`--win-update-url` *url*</a>
 
diff --git a/test/jdk/tools/jpackage/junit/share/jdk.jpackage/jdk/jpackage/internal/cli/help-windows.txt b/test/jdk/tools/jpackage/junit/share/jdk.jpackage/jdk/jpackage/internal/cli/help-windows.txt
index 7a098b847ad..e30a5bb7f9b 100644
--- a/test/jdk/tools/jpackage/junit/share/jdk.jpackage/jdk/jpackage/internal/cli/help-windows.txt
+++ b/test/jdk/tools/jpackage/junit/share/jdk.jpackage/jdk/jpackage/internal/cli/help-windows.txt
@@ -189,16 +189,20 @@ Platform dependent options for creating the application package:
   --win-help-url <url>
           URL where user can obtain further information or technical support
   --win-menu [<shortcut startup directory>]
-          Request to add a Start menu shortcut for this application
+          Adds a Start menu shortcut for this application, or requests
+          to do so if --win-shortcut-prompt is specified
   --win-menu-group <menu group name>
           Start Menu group this application is placed in
   --win-per-user-install
-          Request to perform an install on a per-user basis
+          Installs the application on a per-user basis.
+          Without this option installs per-machine
   --win-shortcut [<shortcut startup directory>]
-          Request to add desktop shortcut for this application
+          Adds a desktop shortcut for this application, or requests
+          to do so if --win-shortcut-prompt is specified
   --win-shortcut-prompt
-          Adds a dialog to enable the user to choose if shortcuts
-          will be created by installer.
+          Adds a dialog if at least one of --win-menu or --win-shortcut
+          are specified to enable the user to choose if these shortcuts
+          will be created by the installer
   --win-update-url <url>
           URL of available application update information
   --win-upgrade-uuid <uuid>