diff --git a/cmd/arduino-app-cli/app/stop.go b/cmd/arduino-app-cli/app/stop.go
index debf40e7..eff55dbd 100644
--- a/cmd/arduino-app-cli/app/stop.go
+++ b/cmd/arduino-app-cli/app/stop.go
@@ -22,6 +22,7 @@ import (
 	"github.com/spf13/cobra"
 
 	"github.com/arduino/arduino-app-cli/cmd/arduino-app-cli/completion"
+	"github.com/arduino/arduino-app-cli/cmd/arduino-app-cli/internal/servicelocator"
 	"github.com/arduino/arduino-app-cli/cmd/feedback"
 	"github.com/arduino/arduino-app-cli/internal/orchestrator"
 	"github.com/arduino/arduino-app-cli/internal/orchestrator/app"
@@ -53,7 +54,7 @@ func newStopCmd(cfg config.Configuration) *cobra.Command {
 func stopHandler(ctx context.Context, app app.ArduinoApp) error {
 	out, _, getResult := feedback.OutputStreams()
 
-	for message := range orchestrator.StopApp(ctx, app) {
+	for message := range orchestrator.StopApp(ctx, servicelocator.GetDockerClient(), app) {
 		switch message.GetType() {
 		case orchestrator.ProgressType:
 			fmt.Fprintf(out, "Progress[%s]: %.0f%%\n", message.GetProgress().Name, message.GetProgress().Progress)
diff --git a/internal/api/api.go b/internal/api/api.go
index 08d31d84..65c66771 100644
--- a/internal/api/api.go
+++ b/internal/api/api.go
@@ -81,7 +81,7 @@ func NewHTTPRouter(
 	mux.Handle("POST /v1/apps/{appID}/start", handlers.HandleAppStart(dockerClient, provisioner, modelsIndex, bricksIndex, idProvider, cfg, staticStore))
 	mux.Handle("POST /v1/apps/{appID}/stop", handlers.HandleAppStop(dockerClient, idProvider))
 	mux.Handle("POST /v1/apps/{appID}/clone", handlers.HandleAppClone(dockerClient, idProvider, cfg))
-	mux.Handle("DELETE /v1/apps/{appID}", handlers.HandleAppDelete(idProvider))
+	mux.Handle("DELETE /v1/apps/{appID}", handlers.HandleAppDelete(dockerClient, idProvider))
 	mux.Handle("GET /v1/apps/{appID}/exposed-ports", handlers.HandleAppPorts(bricksIndex, idProvider))
 	mux.Handle("PUT /v1/apps/{appID}/sketch/libraries/{libRef}", handlers.HandleSketchAddLibrary(idProvider))
 	mux.Handle("DELETE /v1/apps/{appID}/sketch/libraries/{libRef}", handlers.HandleSketchRemoveLibrary(idProvider))
diff --git a/internal/api/handlers/app_delete.go b/internal/api/handlers/app_delete.go
index 864dd405..6503d124 100644
--- a/internal/api/handlers/app_delete.go
+++ b/internal/api/handlers/app_delete.go
@@ -19,13 +19,18 @@ import (
 	"log/slog"
 	"net/http"
 
+	"github.com/docker/cli/cli/command"
+
 	"github.com/arduino/arduino-app-cli/internal/api/models"
 	"github.com/arduino/arduino-app-cli/internal/orchestrator"
 	"github.com/arduino/arduino-app-cli/internal/orchestrator/app"
 	"github.com/arduino/arduino-app-cli/internal/render"
 )
 
-func HandleAppDelete(idProvider *app.IDProvider) http.HandlerFunc {
+func HandleAppDelete(
+	dockerClient command.Cli,
+	idProvider *app.IDProvider,
+) http.HandlerFunc {
 	return func(w http.ResponseWriter, r *http.Request) {
 		id, err := idProvider.IDFromBase64(r.PathValue("appID"))
 		if err != nil {
@@ -44,7 +49,7 @@ func HandleAppDelete(idProvider *app.IDProvider) http.HandlerFunc {
 			return
 		}
 
-		err = orchestrator.DeleteApp(r.Context(), app)
+		err = orchestrator.DeleteApp(r.Context(), dockerClient, app)
 		if err != nil {
 			slog.Error("Unable to delete the app", slog.String("error", err.Error()))
 			render.EncodeResponse(w, http.StatusInternalServerError, models.ErrorResponse{Details: "unable to delete the app"})
diff --git a/internal/api/handlers/app_stop.go b/internal/api/handlers/app_stop.go
index 0b9ec8c0..f5a9979c 100644
--- a/internal/api/handlers/app_stop.go
+++ b/internal/api/handlers/app_stop.go
@@ -60,7 +60,7 @@ func HandleAppStop(
 		type log struct {
 			Message string `json:"message"`
 		}
-		for item := range orchestrator.StopApp(r.Context(), app) {
+		for item := range orchestrator.StopApp(r.Context(), dockerClient, app) {
 			switch item.GetType() {
 			case orchestrator.ProgressType:
 				sseStream.Send(render.SSEEvent{Type: "progress", Data: progress(*item.GetProgress())})
diff --git a/internal/orchestrator/cache.go b/internal/orchestrator/cache.go
index 62b3a950..b4134ff6 100644
--- a/internal/orchestrator/cache.go
+++ b/internal/orchestrator/cache.go
@@ -32,7 +32,7 @@ func CleanAppCache(
 			return ErrCleanCacheRunningApp
 		}
 		// We try to remove docker related resources at best effort
-		for range StopAndDestroyApp(ctx, app) {
+		for range StopAndDestroyApp(ctx, docker, app) {
 			// just consume the iterator
 		}
 	}
diff --git a/internal/orchestrator/orchestrator.go b/internal/orchestrator/orchestrator.go
index 19181998..7f5b6e93 100644
--- a/internal/orchestrator/orchestrator.go
+++ b/internal/orchestrator/orchestrator.go
@@ -377,11 +377,21 @@ func getVideoDevices() map[int]string {
 	return deviceMap
 }
 
-func stopAppWithCmd(ctx context.Context, app app.ArduinoApp, cmd string) iter.Seq[StreamMessage] {
+func stopAppWithCmd(ctx context.Context, docker command.Cli, app app.ArduinoApp, cmd string) iter.Seq[StreamMessage] {
 	return func(yield func(StreamMessage) bool) {
 		ctx, cancel := context.WithCancel(ctx)
 		defer cancel()
 
+		appStatus, err := getAppStatus(ctx, docker, app)
+		if err != nil {
+			yield(StreamMessage{error: err})
+			return
+		}
+		if appStatus.Status != StatusStarting && appStatus.Status != StatusRunning {
+			yield(StreamMessage{data: fmt.Sprintf("app %q is not running", app.Name)})
+			return
+		}
+
 		if !yield(StreamMessage{data: fmt.Sprintf("Stopping app %q", app.Name)}) {
 			return
 		}
@@ -395,6 +405,7 @@ func stopAppWithCmd(ctx context.Context, app app.ArduinoApp, cmd string) iter.Se
 				return
 			}
 		})
+
 		if app.MainSketchPath != nil {
 			// TODO: check that the app sketch is running before attempting to stop it.
 
@@ -425,12 +436,12 @@ func stopAppWithCmd(ctx context.Context, app app.ArduinoApp, cmd string) iter.Se
 	}
 }
 
-func StopApp(ctx context.Context, app app.ArduinoApp) iter.Seq[StreamMessage] {
-	return stopAppWithCmd(ctx, app, "stop")
+func StopApp(ctx context.Context, dockerClient command.Cli, app app.ArduinoApp) iter.Seq[StreamMessage] {
+	return stopAppWithCmd(ctx, dockerClient, app, "stop")
 }
 
-func StopAndDestroyApp(ctx context.Context, app app.ArduinoApp) iter.Seq[StreamMessage] {
-	return stopAppWithCmd(ctx, app, "down")
+func StopAndDestroyApp(ctx context.Context, dockerClient command.Cli, app app.ArduinoApp) iter.Seq[StreamMessage] {
+	return stopAppWithCmd(ctx, dockerClient, app, "down")
 }
 
 func RestartApp(
@@ -458,7 +469,7 @@ func RestartApp(
 				return
 			}
 
-			stopStream := StopApp(ctx, *runningApp)
+			stopStream := StopApp(ctx, docker, *runningApp)
 			for msg := range stopStream {
 				if !yield(msg) {
 					return
@@ -888,12 +899,19 @@ func CloneApp(
 	return CloneAppResponse{ID: id}, nil
 }
 
-func DeleteApp(ctx context.Context, app app.ArduinoApp) error {
-	for msg := range StopApp(ctx, app) {
-		if msg.error != nil {
-			return fmt.Errorf("failed to stop app: %w", msg.error)
+func DeleteApp(ctx context.Context, dockerClient command.Cli, app app.ArduinoApp) error {
+
+	runningApp, err := getRunningApp(ctx, dockerClient.Client())
+	if err != nil {
+		return err
+	}
+	if runningApp != nil && runningApp.FullPath.EqualsTo(app.FullPath) {
+		// We try to remove docker related resources at best effort
+		for range StopAndDestroyApp(ctx, dockerClient, app) {
+			// just consume the iterator
 		}
 	}
+
 	return app.FullPath.RemoveAll()
 }
 
diff --git a/internal/orchestrator/system.go b/internal/orchestrator/system.go
index 341d6c55..4d9f9a60 100644
--- a/internal/orchestrator/system.go
+++ b/internal/orchestrator/system.go
@@ -235,7 +235,7 @@ func SystemCleanup(ctx context.Context, cfg config.Configuration, staticStore *s
 		feedback.Warnf("failed to get running app - %v", err)
 	}
 	if runningApp != nil {
-		for item := range StopAndDestroyApp(ctx, *runningApp) {
+		for item := range StopAndDestroyApp(ctx, docker, *runningApp) {
 			if item.GetType() == ErrorType {
 				feedback.Warnf("failed to stop and destroy running app - %v", item.GetError())
 				break