diff --git a/docs/api/system.rst b/docs/api/system.rst
index 78ea128f..439373a2 100644
--- a/docs/api/system.rst
+++ b/docs/api/system.rst
@@ -39,7 +39,7 @@ List all registered system commands
             "action": "shutdown",
             "name": "Shutdown",
             "command": "sudo shutdown -h now",
-            "confirm": "You are about to shutdown the system.",
+            "confirm": "<b>You are about to shutdown the system.</b></p><p> This action may disrupt any ongoing print jobs (depending on your printer's controller and general setup that might also apply to prints run directly from your printer's internal storage).",
             "async": true,
             "ignore": true,
             "source": "core",
@@ -49,7 +49,7 @@ List all registered system commands
             "action": "reboot",
             "name": "Reboot",
             "command": "sudo reboot",
-            "confirm": "You are about to reboot the system.",
+            "confirm": "<b>You are about to reboot the system.</b></p><p> This action may disrupt any ongoing print jobs (depending on your printer's controller and general setup that might also apply to prints run directly from your printer's internal storage).",
             "async": true,
             "ignore": true,
             "source": "core",
@@ -59,7 +59,7 @@ List all registered system commands
             "action": "restart",
             "name": "Restart OctoPrint",
             "command": "sudo service octoprint restart",
-            "confirm": "You are about to restart the OctoPrint server.",
+            "confirm": "<b>You are about to restart the OctoPrint server.</b></p><p> This action may disrupt any ongoing print jobs (depending on your printer's controller and general setup that might also apply to prints run directly from your printer's internal storage).",
             "async": true,
             "ignore": true,
             "source": "core",
@@ -100,7 +100,7 @@ List all registered system commands for a source
           "action": "shutdown",
           "name": "Shutdown",
           "command": "sudo shutdown -h now",
-          "confirm": "You are about to shutdown the system.",
+          "confirm": "<b>You are about to shutdown the system.</b></p><p> This action may disrupt any ongoing print jobs (depending on your printer's controller and general setup that might also apply to prints run directly from your printer's internal storage).",
           "async": true,
           "ignore": true,
           "source": "core",
@@ -110,7 +110,7 @@ List all registered system commands for a source
           "action": "reboot",
           "name": "Reboot",
           "command": "sudo reboot",
-          "confirm": "You are about to reboot the system.",
+          "confirm": "<b>You are about to reboot the system.</b></p><p> This action may disrupt any ongoing print jobs (depending on your printer's controller and general setup that might also apply to prints run directly from your printer's internal storage).",
           "async": true,
           "ignore": true,
           "source": "core",
@@ -120,7 +120,7 @@ List all registered system commands for a source
           "action": "restart",
           "name": "Restart OctoPrint",
           "command": "sudo service octoprint restart",
-          "confirm": "You are about to restart the OctoPrint server.",
+          "confirm": "<b>You are about to restart the OctoPrint server.</b></p><p> This action may disrupt any ongoing print jobs (depending on your printer's controller and general setup that might also apply to prints run directly from your printer's internal storage).",
           "async": true,
           "ignore": true,
           "source": "core",
diff --git a/src/octoprint/plugins/pluginmanager/static/js/pluginmanager.js b/src/octoprint/plugins/pluginmanager/static/js/pluginmanager.js
index 9663cc61..6984644f 100644
--- a/src/octoprint/plugins/pluginmanager/static/js/pluginmanager.js
+++ b/src/octoprint/plugins/pluginmanager/static/js/pluginmanager.js
@@ -731,7 +731,7 @@ $(function() {
                                     if (restartClicked) return;
                                     restartClicked = true;
                                     showConfirmationDialog({
-                                        message: gettext("This will restart your OctoPrint server."),
+                                        message: gettext("<b>This will restart your OctoPrint server.</b></p><p> This action may disrupt any ongoing print jobs (depending on your printer's controller and general setup that might also apply to prints run directly from your printer's internal storage)."),
                                         onproceed: function() {
                                             OctoPrint.system.executeCommand("core", "restart")
                                                 .done(function() {
diff --git a/src/octoprint/server/api/system.py b/src/octoprint/server/api/system.py
index e17bdb78..8be2fec2 100644
--- a/src/octoprint/server/api/system.py
+++ b/src/octoprint/server/api/system.py
@@ -167,19 +167,19 @@ def _get_core_command_specs():
 		shutdown=dict(
 			command=s().get(["server", "commands", "systemShutdownCommand"]),
 			name=gettext("Shutdown system"),
-			confirm=gettext("You are about to shutdown the system.")),
+			confirm=gettext("<b>You are about to shutdown the system.</b></p><p> This action may disrupt any ongoing print jobs (depending on your printer's controller and general setup that might also apply to prints run directly from your printer's internal storage).")),
 		reboot=dict(
 			command=s().get(["server", "commands", "systemRestartCommand"]),
 			name=gettext("Reboot system"),
-			confirm=gettext("You are about to reboot the system.")),
+			confirm=gettext("<b>You are about to reboot the system.</b></p><p> This action may disrupt any ongoing print jobs (depending on your printer's controller and general setup that might also apply to prints run directly from your printer's internal storage).")),
 		restart=dict(
 			command=s().get(["server", "commands", "serverRestartCommand"]),
 			name=gettext("Restart OctoPrint"),
-			confirm=gettext("You are about to restart the OctoPrint server.")),
+			confirm=gettext("<b>You are about to restart the OctoPrint server.</b></p><p> This action may disrupt any ongoing print jobs (depending on your printer's controller and general setup that might also apply to prints run directly from your printer's internal storage).")),
 		restart_safe=dict(
 			command=s().get(["server", "commands", "serverRestartCommand"]),
 			name=gettext("Restart OctoPrint in safe mode"),
-			confirm=gettext("You are about to restart the OctoPrint server in safe mode."),
+			confirm=gettext("<b>You are about to restart the OctoPrint server in safe mode.</b></p><p>  This action may disrupt any ongoing print jobs (depending on your printer's controller and general setup that might also apply to prints run directly from your printer's internal storage)."),
 			before=enable_safe_mode)
 	)