diff --git a/internal/usbgadget/config.go b/internal/usbgadget/config.go
index 6d1bd391..8333a365 100644
--- a/internal/usbgadget/config.go
+++ b/internal/usbgadget/config.go
@@ -24,6 +24,14 @@ type gadgetConfigItemWithKey struct {
 
 type orderedGadgetConfigItems []gadgetConfigItemWithKey
 
+type UsbResetMode uint8
+
+const (
+	UsbResetNever    UsbResetMode = 0 // never reset the usb gadget
+	UsbResetAlways   UsbResetMode = 1 // always reset the usb gadget
+	UsbResetOnDemand UsbResetMode = 2 // reset the usb gadget when needed
+)
+
 var defaultGadgetConfig = map[string]gadgetConfigItem{
 	"base": {
 		order: 0,
@@ -177,7 +185,7 @@ func (u *UsbGadget) Init() error {
 
 	u.udc = udcs[0]
 
-	err := u.configureUsbGadget(false)
+	err := u.configureUsbGadget(UsbResetAlways)
 	if err != nil {
 		return u.logError("unable to initialize USB stack", err)
 	}
@@ -185,13 +193,13 @@ func (u *UsbGadget) Init() error {
 	return nil
 }
 
-func (u *UsbGadget) UpdateGadgetConfig() error {
+func (u *UsbGadget) UpdateGadgetConfig(resetUsbMode UsbResetMode) error {
 	u.configLock.Lock()
 	defer u.configLock.Unlock()
 
 	u.loadGadgetConfig()
 
-	err := u.configureUsbGadget(true)
+	err := u.configureUsbGadget(resetUsbMode)
 	if err != nil {
 		return u.logError("unable to update gadget config", err)
 	}
@@ -199,14 +207,35 @@ 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(resetUsbMode UsbResetMode) error {
+	f := func(resetUsbAfter bool) func() error {
+		return func() error {
+			u.tx.MountConfigFS()
+			u.tx.CreateConfigPath()
+			u.tx.WriteGadgetConfig()
+			if resetUsbAfter {
+				u.tx.RebindUsb(true)
+			}
+			return nil
 		}
+	}
+
+	// initial attempt to configure the gadget
+	err := u.WithTransaction(f(resetUsbMode == UsbResetAlways))
+	if err == nil {
 		return nil
-	})
+	}
+
+	// if the initial attempt failed, try to configure the gadget again with the resetUsb flag
+	if resetUsbMode == UsbResetOnDemand {
+		u.log.Warn().Err(err).Msg("initial attempt to configure the gadget failed, resetting USB gadget then trying again")
+		// NOTES: do not use the RebindUsb method here because it will block the transaction
+		if err := u.rebindUsb(true); err != nil {
+			u.log.Warn().Err(err).Msg("failed to reset USB gadget, skipping second attempt")
+			return err
+		}
+		return u.WithTransaction(f(true))
+	}
+
+	return err
 }
diff --git a/jsonrpc.go b/jsonrpc.go
index d30f6669..74a2c788 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(usbgadget.UsbResetAlways)
 }
 
 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(resetUsbMode usbgadget.UsbResetMode) error {
+	if err := gadget.UpdateGadgetConfig(resetUsbMode); 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(usbgadget.UsbResetOnDemand)
 }
 
 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(usbgadget.UsbResetAlways)
 }
 
 func rpcSetCloudUrl(apiUrl string, appUrl string) error {
diff --git a/ui/src/routes/devices.$id.settings.general.reboot.tsx b/ui/src/routes/devices.$id.settings.general.reboot.tsx
index b8c32b51..6b3f512f 100644
--- a/ui/src/routes/devices.$id.settings.general.reboot.tsx
+++ b/ui/src/routes/devices.$id.settings.general.reboot.tsx
@@ -6,6 +6,7 @@ import { Button } from "@components/Button";
 import { useFailsafeModeStore } from "@/hooks/stores";
 import { sleep } from "@/utils";
 import { m } from "@localizations/messages.js";
+import { sleep } from "@/utils";
 
 import LoadingSpinner from "../components/LoadingSpinner";
 import { useDeviceUiNavigation } from "../hooks/useAppNavigation";
diff --git a/usb_mass_storage.go b/usb_mass_storage.go
index 0f1f4b93..85921153 100644
--- a/usb_mass_storage.go
+++ b/usb_mass_storage.go
@@ -19,13 +19,10 @@ import (
 	"github.com/pion/webrtc/v4"
 	"github.com/psanford/httpreadat"
 
+	"github.com/jetkvm/kvm/internal/usbgadget"
 	"github.com/jetkvm/kvm/resource"
 )
 
-func writeFile(path string, data string) error {
-	return os.WriteFile(path, []byte(data), 0644)
-}
-
 func getMassStorageImage() (string, error) {
 	massStorageFunctionPath, err := gadget.GetPath("mass_storage_lun0")
 	if err != nil {
@@ -40,14 +37,15 @@ func getMassStorageImage() (string, error) {
 }
 
 func setMassStorageImage(imagePath string) error {
-	massStorageFunctionPath, err := gadget.GetPath("mass_storage_lun0")
+	err, _ := gadget.OverrideGadgetConfig("mass_storage_lun0", "file", imagePath)
 	if err != nil {
-		return fmt.Errorf("failed to get mass storage path: %w", err)
+		return fmt.Errorf("failed to set mass storage path: %w", err)
 	}
 
-	if err := writeFile(path.Join(massStorageFunctionPath, "file"), imagePath); err != nil {
-		return fmt.Errorf("failed to set image path: %w", err)
+	if err := gadget.UpdateGadgetConfig(usbgadget.UsbResetOnDemand); err != nil {
+		return fmt.Errorf("failed to update gadget config: %w", err)
 	}
+
 	return nil
 }
 
@@ -66,7 +64,7 @@ func setMassStorageMode(cdrom bool) error {
 		return nil
 	}
 
-	return gadget.UpdateGadgetConfig()
+	return gadget.UpdateGadgetConfig(usbgadget.UsbResetOnDemand)
 }
 
 func mountImage(imagePath string) error {