diff --git a/internal/usbgadget/config.go b/internal/usbgadget/config.go
index 6d1bd391..8cbdf081 100644
--- a/internal/usbgadget/config.go
+++ b/internal/usbgadget/config.go
@@ -177,7 +177,7 @@ func (u *UsbGadget) Init() error {
 
 	u.udc = udcs[0]
 
-	err := u.configureUsbGadget(false)
+	err := u.configureUsbGadget(false, true)
 	if err != nil {
 		return u.logError("unable to initialize USB stack", err)
 	}
@@ -185,13 +185,13 @@ func (u *UsbGadget) Init() error {
 	return nil
 }
 
-func (u *UsbGadget) UpdateGadgetConfig() error {
+func (u *UsbGadget) UpdateGadgetConfig(resetUsbIfNeeded bool) error {
 	u.configLock.Lock()
 	defer u.configLock.Unlock()
 
 	u.loadGadgetConfig()
 
-	err := u.configureUsbGadget(true)
+	err := u.configureUsbGadget(true, resetUsbIfNeeded)
 	if err != nil {
 		return u.logError("unable to update gadget config", err)
 	}
@@ -199,14 +199,28 @@ func (u *UsbGadget) UpdateGadgetConfig() error {
 	return nil
 }
 
-func (u *UsbGadget) configureUsbGadget(resetUsb bool) error {
-	return u.WithTransaction(func() error {
-		u.tx.MountConfigFS()
-		u.tx.CreateConfigPath()
-		u.tx.WriteGadgetConfig()
-		if resetUsb {
-			u.tx.RebindUsb(true)
+func (u *UsbGadget) configureUsbGadget(resetUsb bool, resetUsbIfNeeded bool) error {
+	f := func(resetUsbBefore bool, resetUsbAfter bool) func() error {
+		return func() error {
+			if resetUsbBefore {
+				u.tx.RebindUsb(true)
+			}
+			u.tx.MountConfigFS()
+			u.tx.CreateConfigPath()
+			u.tx.WriteGadgetConfig()
+			if resetUsbAfter {
+				u.tx.RebindUsb(true)
+			}
+			return nil
 		}
-		return nil
-	})
+	}
+
+	// initial attempt to configure the gadget
+	err := u.WithTransaction(f(false, resetUsb))
+	if err != nil && !resetUsbIfNeeded {
+		return err
+	}
+
+	// if the initial attempt failed, try to configure the gadget again with the resetUsb flag
+	return u.WithTransaction(f(true, resetUsb))
 }
diff --git a/jsonrpc.go b/jsonrpc.go
index 5ed90a7a..4d8695c2 100644
--- a/jsonrpc.go
+++ b/jsonrpc.go
@@ -678,7 +678,7 @@ func rpcSetUsbConfig(usbConfig usbgadget.Config) error {
 	LoadConfig()
 	config.UsbConfig = &usbConfig
 	gadget.SetGadgetConfig(config.UsbConfig)
-	return updateUsbRelatedConfig()
+	return updateUsbRelatedConfig(false)
 }
 
 func rpcGetWakeOnLanDevices() ([]WakeOnLanDevice, error) {
@@ -890,8 +890,8 @@ func rpcGetUsbDevices() (usbgadget.Devices, error) {
 	return *config.UsbDevices, nil
 }
 
-func updateUsbRelatedConfig() error {
-	if err := gadget.UpdateGadgetConfig(); err != nil {
+func updateUsbRelatedConfig(resetUsbIfNeeded bool) error {
+	if err := gadget.UpdateGadgetConfig(resetUsbIfNeeded); err != nil {
 		return fmt.Errorf("failed to write gadget config: %w", err)
 	}
 	if err := SaveConfig(); err != nil {
@@ -903,7 +903,7 @@ func updateUsbRelatedConfig() error {
 func rpcSetUsbDevices(usbDevices usbgadget.Devices) error {
 	config.UsbDevices = &usbDevices
 	gadget.SetGadgetDevices(config.UsbDevices)
-	return updateUsbRelatedConfig()
+	return updateUsbRelatedConfig(false)
 }
 
 func rpcSetUsbDeviceState(device string, enabled bool) error {
@@ -920,7 +920,7 @@ func rpcSetUsbDeviceState(device string, enabled bool) error {
 		return fmt.Errorf("invalid device: %s", device)
 	}
 	gadget.SetGadgetDevices(config.UsbDevices)
-	return updateUsbRelatedConfig()
+	return updateUsbRelatedConfig(false)
 }
 
 func rpcSetCloudUrl(apiUrl string, appUrl string) error {
diff --git a/ui/src/routes/devices.$id.settings.advanced.tsx b/ui/src/routes/devices.$id.settings.advanced.tsx
index dbc98a75..4c3c9e94 100644
--- a/ui/src/routes/devices.$id.settings.advanced.tsx
+++ b/ui/src/routes/devices.$id.settings.advanced.tsx
@@ -12,6 +12,7 @@ import { TextAreaWithLabel } from "@components/TextArea";
 import { isOnDevice } from "@/main";
 import notifications from "@/notifications";
 import { m } from "@localizations/messages.js";
+import { sleep } from "@/utils";
 
 export default function SettingsAdvancedRoute() {
   const { send } = useJsonRpc();
@@ -311,7 +312,7 @@ export default function SettingsAdvancedRoute() {
                 size="SM"
                 theme="light"
                 text={m.advanced_reset_config_button()}
-                onClick={() => {
+                onClick={async () => {
                   handleResetConfig();
                   // Add 2s delay between resetting the configuration and calling reload() to prevent reload from interrupting the RPC call to reset things.
                   await sleep(2000);
diff --git a/ui/src/routes/devices.$id.settings.general.reboot.tsx b/ui/src/routes/devices.$id.settings.general.reboot.tsx
index 5a4474e6..fc0feeaa 100644
--- a/ui/src/routes/devices.$id.settings.general.reboot.tsx
+++ b/ui/src/routes/devices.$id.settings.general.reboot.tsx
@@ -4,12 +4,13 @@ import { useNavigate } from "react-router";
 import { useJsonRpc } from "@hooks/useJsonRpc";
 import { Button } from "@components/Button";
 import { m } from "@localizations/messages.js";
+import { sleep } from "@/utils";
 
 export default function SettingsGeneralRebootRoute() {
   const navigate = useNavigate();
   const { send } = useJsonRpc();
   
-  const onClose = useCallback(() => {
+  const onClose = useCallback(async () => {
     navigate(".."); // back to the devices.$id.settings page
     // Add 1s delay between navigation and calling reload() to prevent reload from interrupting the navigation.
     await sleep(1000);
diff --git a/ui/src/routes/devices.$id.settings.general.update.tsx b/ui/src/routes/devices.$id.settings.general.update.tsx
index 3a52eee2..285ce940 100644
--- a/ui/src/routes/devices.$id.settings.general.update.tsx
+++ b/ui/src/routes/devices.$id.settings.general.update.tsx
@@ -21,7 +21,7 @@ export default function SettingsGeneralUpdateRoute() {
   const { setModalView, otaState } = useUpdateStore();
   const { send } = useJsonRpc();
 
-  const onClose = useCallback(() => {
+  const onClose = useCallback(async () => {
     navigate(".."); // back to the devices.$id.settings page
     // Add 1s delay between navigation and calling reload() to prevent reload from interrupting the navigation.
     await sleep(1000);
diff --git a/usb_mass_storage.go b/usb_mass_storage.go
index 0f1f4b93..9a112e3a 100644
--- a/usb_mass_storage.go
+++ b/usb_mass_storage.go
@@ -66,7 +66,7 @@ func setMassStorageMode(cdrom bool) error {
 		return nil
 	}
 
-	return gadget.UpdateGadgetConfig()
+	return gadget.UpdateGadgetConfig(true)
 }
 
 func mountImage(imagePath string) error {