diff --git a/arduino/discovery/discovery.go b/arduino/discovery/discovery.go
index b8c3537b5f4..1832f1e77d3 100644
--- a/arduino/discovery/discovery.go
+++ b/arduino/discovery/discovery.go
@@ -97,6 +97,12 @@ type Port struct {
 
 var tr = i18n.Tr
 
+// Equals returns true if the given port has the same address and protocol
+// of the current port.
+func (p *Port) Equals(o *Port) bool {
+	return p.Address == o.Address && p.Protocol == o.Protocol
+}
+
 // ToRPC converts Port into rpc.Port
 func (p *Port) ToRPC() *rpc.Port {
 	props := p.Properties
@@ -113,6 +119,24 @@ func (p *Port) ToRPC() *rpc.Port {
 	}
 }
 
+// PortFromRPCPort converts an *rpc.Port to a *Port
+func PortFromRPCPort(o *rpc.Port) (p *Port) {
+	if o == nil {
+		return nil
+	}
+	res := &Port{
+		Address:       o.Address,
+		AddressLabel:  o.Label,
+		Protocol:      o.Protocol,
+		ProtocolLabel: o.ProtocolLabel,
+		HardwareID:    o.HardwareId,
+	}
+	if o.Properties != nil {
+		res.Properties = properties.NewFromHashmap(o.Properties)
+	}
+	return res
+}
+
 func (p *Port) String() string {
 	if p == nil {
 		return "none"
@@ -120,6 +144,18 @@ func (p *Port) String() string {
 	return p.Address
 }
 
+// Clone creates a copy of this Port
+func (p *Port) Clone() *Port {
+	if p == nil {
+		return nil
+	}
+	var res Port = *p
+	if p.Properties != nil {
+		res.Properties = p.Properties.Clone()
+	}
+	return &res
+}
+
 // Event is a pluggable discovery event
 type Event struct {
 	Type        string
diff --git a/arduino/discovery/discovery_client/main.go b/arduino/discovery/discovery_client/main.go
index dd556691fe4..b9e1cfd0988 100644
--- a/arduino/discovery/discovery_client/main.go
+++ b/arduino/discovery/discovery_client/main.go
@@ -51,10 +51,12 @@ func main() {
 		fmt.Printf("   Address: %s\n", port.Address)
 		fmt.Printf("  Protocol: %s\n", port.Protocol)
 		if ev.Type == "add" {
-			keys := port.Properties.Keys()
-			sort.Strings(keys)
-			for _, k := range keys {
-				fmt.Printf("            %s=%s\n", k, port.Properties.Get(k))
+			if port.Properties != nil {
+				keys := port.Properties.Keys()
+				sort.Strings(keys)
+				for _, k := range keys {
+					fmt.Printf("            %s=%s\n", k, port.Properties.Get(k))
+				}
 			}
 		}
 		fmt.Println()
diff --git a/commands/board/list.go b/commands/board/list.go
index 5098ced4cfd..1ac055253b9 100644
--- a/commands/board/list.go
+++ b/commands/board/list.go
@@ -34,6 +34,7 @@ import (
 	"github.com/arduino/arduino-cli/commands"
 	"github.com/arduino/arduino-cli/internal/inventory"
 	rpc "github.com/arduino/arduino-cli/rpc/cc/arduino/cli/commands/v1"
+	"github.com/arduino/go-properties-orderedmap"
 	"github.com/pkg/errors"
 	"github.com/sirupsen/logrus"
 )
@@ -128,20 +129,22 @@ func apiByVidPid(vid, pid string) ([]*rpc.BoardListItem, error) {
 	}, nil
 }
 
-func identifyViaCloudAPI(port *discovery.Port) ([]*rpc.BoardListItem, error) {
+func identifyViaCloudAPI(props *properties.Map) ([]*rpc.BoardListItem, error) {
 	// If the port is not USB do not try identification via cloud
-	id := port.Properties
-	if !id.ContainsKey("vid") || !id.ContainsKey("pid") {
+	if !props.ContainsKey("vid") || !props.ContainsKey("pid") {
 		return nil, nil
 	}
 
 	logrus.Debug("Querying builder API for board identification...")
-	return cachedAPIByVidPid(id.Get("vid"), id.Get("pid"))
+	return cachedAPIByVidPid(props.Get("vid"), props.Get("pid"))
 }
 
 // identify returns a list of boards checking first the installed platforms or the Cloud API
 func identify(pme *packagemanager.Explorer, port *discovery.Port) ([]*rpc.BoardListItem, error) {
 	boards := []*rpc.BoardListItem{}
+	if port.Properties == nil {
+		return boards, nil
+	}
 
 	// first query installed cores through the Package Manager
 	logrus.Debug("Querying installed cores for board identification...")
@@ -167,7 +170,7 @@ func identify(pme *packagemanager.Explorer, port *discovery.Port) ([]*rpc.BoardL
 	// if installed cores didn't recognize the board, try querying
 	// the builder API if the board is a USB device port
 	if len(boards) == 0 {
-		items, err := identifyViaCloudAPI(port)
+		items, err := identifyViaCloudAPI(port.Properties)
 		if err != nil {
 			// this is bad, but keep going
 			logrus.WithError(err).Debug("Error querying builder API")
diff --git a/commands/board/list_test.go b/commands/board/list_test.go
index cf1dca37e4c..f99d942cf29 100644
--- a/commands/board/list_test.go
+++ b/commands/board/list_test.go
@@ -103,10 +103,7 @@ func TestGetByVidPidMalformedResponse(t *testing.T) {
 }
 
 func TestBoardDetectionViaAPIWithNonUSBPort(t *testing.T) {
-	port := &discovery.Port{
-		Properties: properties.NewMap(),
-	}
-	items, err := identifyViaCloudAPI(port)
+	items, err := identifyViaCloudAPI(properties.NewMap())
 	require.NoError(t, err)
 	require.Empty(t, items)
 }
diff --git a/commands/daemon/daemon.go b/commands/daemon/daemon.go
index bcf173381c7..1cb5a667b60 100644
--- a/commands/daemon/daemon.go
+++ b/commands/daemon/daemon.go
@@ -297,15 +297,27 @@ func (s *ArduinoCoreServerImpl) PlatformList(ctx context.Context, req *rpc.Platf
 // Upload FIXMEDOC
 func (s *ArduinoCoreServerImpl) Upload(req *rpc.UploadRequest, stream rpc.ArduinoCoreService_UploadServer) error {
 	syncSend := NewSynchronizedSend(stream.Send)
-	outStream := feedStreamTo(func(data []byte) { syncSend.Send(&rpc.UploadResponse{OutStream: data}) })
-	errStream := feedStreamTo(func(data []byte) { syncSend.Send(&rpc.UploadResponse{ErrStream: data}) })
-	err := upload.Upload(stream.Context(), req, outStream, errStream)
+	outStream := feedStreamTo(func(data []byte) {
+		syncSend.Send(&rpc.UploadResponse{
+			Message: &rpc.UploadResponse_OutStream{OutStream: data},
+		})
+	})
+	errStream := feedStreamTo(func(data []byte) {
+		syncSend.Send(&rpc.UploadResponse{
+			Message: &rpc.UploadResponse_ErrStream{ErrStream: data},
+		})
+	})
+	res, err := upload.Upload(stream.Context(), req, outStream, errStream)
 	outStream.Close()
 	errStream.Close()
-	if err != nil {
-		return convertErrorToRPCStatus(err)
+	if res != nil {
+		syncSend.Send(&rpc.UploadResponse{
+			Message: &rpc.UploadResponse_Result{
+				Result: res,
+			},
+		})
 	}
-	return nil
+	return convertErrorToRPCStatus(err)
 }
 
 // UploadUsingProgrammer FIXMEDOC
diff --git a/commands/upload/burnbootloader.go b/commands/upload/burnbootloader.go
index f47e22fd239..99efe2be757 100644
--- a/commands/upload/burnbootloader.go
+++ b/commands/upload/burnbootloader.go
@@ -39,7 +39,7 @@ func BurnBootloader(ctx context.Context, req *rpc.BurnBootloaderRequest, outStre
 	}
 	defer release()
 
-	err := runProgramAction(
+	_, err := runProgramAction(
 		pme,
 		nil, // sketch
 		"",  // importFile
diff --git a/commands/upload/upload.go b/commands/upload/upload.go
index 8de4bc009f6..75f8aae9238 100644
--- a/commands/upload/upload.go
+++ b/commands/upload/upload.go
@@ -21,16 +21,19 @@ import (
 	"io"
 	"path/filepath"
 	"strings"
+	"time"
 
 	"github.com/arduino/arduino-cli/arduino"
 	"github.com/arduino/arduino-cli/arduino/cores"
 	"github.com/arduino/arduino-cli/arduino/cores/packagemanager"
+	"github.com/arduino/arduino-cli/arduino/discovery"
 	"github.com/arduino/arduino-cli/arduino/globals"
 	"github.com/arduino/arduino-cli/arduino/serialutils"
 	"github.com/arduino/arduino-cli/arduino/sketch"
 	"github.com/arduino/arduino-cli/commands"
 	"github.com/arduino/arduino-cli/executils"
 	"github.com/arduino/arduino-cli/i18n"
+	f "github.com/arduino/arduino-cli/internal/algorithms"
 	rpc "github.com/arduino/arduino-cli/rpc/cc/arduino/cli/commands/v1"
 	paths "github.com/arduino/go-paths-helper"
 	properties "github.com/arduino/go-properties-orderedmap"
@@ -123,7 +126,7 @@ func getUserFields(toolID string, platformRelease *cores.PlatformRelease) []*rpc
 }
 
 // Upload FIXMEDOC
-func Upload(ctx context.Context, req *rpc.UploadRequest, outStream io.Writer, errStream io.Writer) error {
+func Upload(ctx context.Context, req *rpc.UploadRequest, outStream io.Writer, errStream io.Writer) (*rpc.UploadResult, error) {
 	logrus.Tracef("Upload %s on %s started", req.GetSketchPath(), req.GetFqbn())
 
 	// TODO: make a generic function to extract sketch from request
@@ -131,16 +134,16 @@ func Upload(ctx context.Context, req *rpc.UploadRequest, outStream io.Writer, er
 	sketchPath := paths.New(req.GetSketchPath())
 	sk, err := sketch.New(sketchPath)
 	if err != nil && req.GetImportDir() == "" && req.GetImportFile() == "" {
-		return &arduino.CantOpenSketchError{Cause: err}
+		return nil, &arduino.CantOpenSketchError{Cause: err}
 	}
 
-	pme, release := commands.GetPackageManagerExplorer(req)
+	pme, pmeRelease := commands.GetPackageManagerExplorer(req)
 	if pme == nil {
-		return &arduino.InvalidInstanceError{}
+		return nil, &arduino.InvalidInstanceError{}
 	}
-	defer release()
+	defer pmeRelease()
 
-	if err := runProgramAction(
+	updatedPort, err := runProgramAction(
 		pme,
 		sk,
 		req.GetImportFile(),
@@ -155,11 +158,14 @@ func Upload(ctx context.Context, req *rpc.UploadRequest, outStream io.Writer, er
 		errStream,
 		req.GetDryRun(),
 		req.GetUserFields(),
-	); err != nil {
-		return err
+	)
+	if err != nil {
+		return nil, err
 	}
 
-	return nil
+	return &rpc.UploadResult{
+		UpdatedUploadPort: updatedPort,
+	}, nil
 }
 
 // UsingProgrammer FIXMEDOC
@@ -169,7 +175,7 @@ func UsingProgrammer(ctx context.Context, req *rpc.UploadUsingProgrammerRequest,
 	if req.GetProgrammer() == "" {
 		return &arduino.MissingProgrammerError{}
 	}
-	err := Upload(ctx, &rpc.UploadRequest{
+	_, err := Upload(ctx, &rpc.UploadRequest{
 		Instance:   req.GetInstance(),
 		SketchPath: req.GetSketchPath(),
 		ImportFile: req.GetImportFile(),
@@ -186,36 +192,38 @@ func UsingProgrammer(ctx context.Context, req *rpc.UploadUsingProgrammerRequest,
 
 func runProgramAction(pme *packagemanager.Explorer,
 	sk *sketch.Sketch,
-	importFile, importDir, fqbnIn string, port *rpc.Port,
+	importFile, importDir, fqbnIn string, userPort *rpc.Port,
 	programmerID string,
 	verbose, verify, burnBootloader bool,
 	outStream, errStream io.Writer,
-	dryRun bool, userFields map[string]string) error {
-
-	if burnBootloader && programmerID == "" {
-		return &arduino.MissingProgrammerError{}
-	}
+	dryRun bool, userFields map[string]string,
+) (*rpc.Port, error) {
+	port := discovery.PortFromRPCPort(userPort)
 	if port == nil || (port.Address == "" && port.Protocol == "") {
 		// For no-port uploads use "default" protocol
-		port = &rpc.Port{Protocol: "default"}
+		port = &discovery.Port{Protocol: "default"}
 	}
 	logrus.WithField("port", port).Tracef("Upload port")
 
+	if burnBootloader && programmerID == "" {
+		return nil, &arduino.MissingProgrammerError{}
+	}
+
 	fqbn, err := cores.ParseFQBN(fqbnIn)
 	if err != nil {
-		return &arduino.InvalidFQBNError{Cause: err}
+		return nil, &arduino.InvalidFQBNError{Cause: err}
 	}
 	logrus.WithField("fqbn", fqbn).Tracef("Detected FQBN")
 
 	// Find target board and board properties
 	_, boardPlatform, board, boardProperties, buildPlatform, err := pme.ResolveFQBN(fqbn)
 	if boardPlatform == nil {
-		return &arduino.PlatformNotFoundError{
+		return nil, &arduino.PlatformNotFoundError{
 			Platform: fmt.Sprintf("%s:%s", fqbn.Package, fqbn.PlatformArch),
 			Cause:    err,
 		}
 	} else if err != nil {
-		return &arduino.UnknownFQBNError{Cause: err}
+		return nil, &arduino.UnknownFQBNError{Cause: err}
 	}
 	logrus.
 		WithField("boardPlatform", boardPlatform).
@@ -232,7 +240,7 @@ func runProgramAction(pme *packagemanager.Explorer,
 			programmer = buildPlatform.Programmers[programmerID]
 		}
 		if programmer == nil {
-			return &arduino.ProgrammerNotFoundError{Programmer: programmerID}
+			return nil, &arduino.ProgrammerNotFoundError{Programmer: programmerID}
 		}
 	}
 
@@ -253,7 +261,7 @@ func runProgramAction(pme *packagemanager.Explorer,
 	}
 	uploadToolID, err := getToolID(props, action, port.Protocol)
 	if err != nil {
-		return err
+		return nil, err
 	}
 
 	var uploadToolPlatform *cores.PlatformRelease
@@ -268,7 +276,7 @@ func runProgramAction(pme *packagemanager.Explorer,
 		Trace("Upload tool")
 
 	if split := strings.Split(uploadToolID, ":"); len(split) > 2 {
-		return &arduino.InvalidPlatformPropertyError{
+		return nil, &arduino.InvalidPlatformPropertyError{
 			Property: fmt.Sprintf("%s.tool.%s", action, port.Protocol), // TODO: Can be done better, maybe inline getToolID(...)
 			Value:    uploadToolID}
 	} else if len(split) == 2 {
@@ -277,12 +285,12 @@ func runProgramAction(pme *packagemanager.Explorer,
 			PlatformArchitecture: boardPlatform.Platform.Architecture,
 		})
 		if p == nil {
-			return &arduino.PlatformNotFoundError{Platform: split[0] + ":" + boardPlatform.Platform.Architecture}
+			return nil, &arduino.PlatformNotFoundError{Platform: split[0] + ":" + boardPlatform.Platform.Architecture}
 		}
 		uploadToolID = split[1]
 		uploadToolPlatform = pme.GetInstalledPlatformRelease(p)
 		if uploadToolPlatform == nil {
-			return &arduino.PlatformNotFoundError{Platform: split[0] + ":" + boardPlatform.Platform.Architecture}
+			return nil, &arduino.PlatformNotFoundError{Platform: split[0] + ":" + boardPlatform.Platform.Architecture}
 		}
 	}
 
@@ -309,7 +317,7 @@ func runProgramAction(pme *packagemanager.Explorer,
 	}
 
 	if !uploadProperties.ContainsKey("upload.protocol") && programmer == nil {
-		return &arduino.ProgrammerRequiredForUploadError{}
+		return nil, &arduino.ProgrammerRequiredForUploadError{}
 	}
 
 	// Set properties for verbose upload
@@ -357,18 +365,35 @@ func runProgramAction(pme *packagemanager.Explorer,
 	if !burnBootloader {
 		importPath, sketchName, err := determineBuildPathAndSketchName(importFile, importDir, sk, fqbn)
 		if err != nil {
-			return &arduino.NotFoundError{Message: tr("Error finding build artifacts"), Cause: err}
+			return nil, &arduino.NotFoundError{Message: tr("Error finding build artifacts"), Cause: err}
 		}
 		if !importPath.Exist() {
-			return &arduino.NotFoundError{Message: tr("Compiled sketch not found in %s", importPath)}
+			return nil, &arduino.NotFoundError{Message: tr("Compiled sketch not found in %s", importPath)}
 		}
 		if !importPath.IsDir() {
-			return &arduino.NotFoundError{Message: tr("Expected compiled sketch in directory %s, but is a file instead", importPath)}
+			return nil, &arduino.NotFoundError{Message: tr("Expected compiled sketch in directory %s, but is a file instead", importPath)}
 		}
 		uploadProperties.SetPath("build.path", importPath)
 		uploadProperties.Set("build.project_name", sketchName)
 	}
 
+	// This context is kept alive for the entire duration of the upload
+	uploadCtx, uploadCompleted := context.WithCancel(context.Background())
+	defer uploadCompleted()
+
+	// Start the upload port change detector.
+	watcher, err := pme.DiscoveryManager().Watch()
+	if err != nil {
+		return nil, err
+	}
+	defer watcher.Close()
+	updatedUploadPort := f.NewFuture[*discovery.Port]()
+	go detectUploadPort(
+		uploadCtx,
+		port, watcher.Feed(),
+		uploadProperties.GetBoolean("upload.wait_for_upload_port"),
+		updatedUploadPort)
+
 	// Force port wait to make easier to unbrick boards like the Arduino Leonardo, or similar with native USB,
 	// when a sketch causes a crash and the native USB serial port is lost.
 	// See https://github.com/arduino/arduino-cli/issues/1943 for the details.
@@ -385,7 +410,7 @@ func runProgramAction(pme *packagemanager.Explorer,
 
 	// If not using programmer perform some action required
 	// to set the board in bootloader mode
-	actualPort := port
+	actualPort := port.Clone()
 	if programmer == nil && !burnBootloader && (port.Protocol == "serial" || forcedSerialPortWait) {
 		// Perform reset via 1200bps touch if requested and wait for upload port also if requested.
 		touch := uploadProperties.GetBoolean("upload.use_1200bps_touch")
@@ -439,6 +464,7 @@ func runProgramAction(pme *packagemanager.Explorer,
 		} else {
 			if newPortAddress != "" {
 				actualPort.Address = newPortAddress
+				actualPort.AddressLabel = newPortAddress
 			}
 		}
 	}
@@ -455,34 +481,144 @@ func runProgramAction(pme *packagemanager.Explorer,
 
 	// Get Port properties gathered using pluggable discovery
 	uploadProperties.Set("upload.port.address", port.Address)
-	uploadProperties.Set("upload.port.label", port.Label)
+	uploadProperties.Set("upload.port.label", port.AddressLabel)
 	uploadProperties.Set("upload.port.protocol", port.Protocol)
 	uploadProperties.Set("upload.port.protocolLabel", port.ProtocolLabel)
-	for prop, value := range actualPort.Properties {
-		uploadProperties.Set(fmt.Sprintf("upload.port.properties.%s", prop), value)
+	if actualPort.Properties != nil {
+		for prop, value := range actualPort.Properties.AsMap() {
+			uploadProperties.Set(fmt.Sprintf("upload.port.properties.%s", prop), value)
+		}
 	}
 
 	// Run recipes for upload
 	toolEnv := pme.GetEnvVarsForSpawnedProcess()
 	if burnBootloader {
 		if err := runTool("erase.pattern", uploadProperties, outStream, errStream, verbose, dryRun, toolEnv); err != nil {
-			return &arduino.FailedUploadError{Message: tr("Failed chip erase"), Cause: err}
+			return nil, &arduino.FailedUploadError{Message: tr("Failed chip erase"), Cause: err}
 		}
 		if err := runTool("bootloader.pattern", uploadProperties, outStream, errStream, verbose, dryRun, toolEnv); err != nil {
-			return &arduino.FailedUploadError{Message: tr("Failed to burn bootloader"), Cause: err}
+			return nil, &arduino.FailedUploadError{Message: tr("Failed to burn bootloader"), Cause: err}
 		}
 	} else if programmer != nil {
 		if err := runTool("program.pattern", uploadProperties, outStream, errStream, verbose, dryRun, toolEnv); err != nil {
-			return &arduino.FailedUploadError{Message: tr("Failed programming"), Cause: err}
+			return nil, &arduino.FailedUploadError{Message: tr("Failed programming"), Cause: err}
 		}
 	} else {
 		if err := runTool("upload.pattern", uploadProperties, outStream, errStream, verbose, dryRun, toolEnv); err != nil {
-			return &arduino.FailedUploadError{Message: tr("Failed uploading"), Cause: err}
+			return nil, &arduino.FailedUploadError{Message: tr("Failed uploading"), Cause: err}
 		}
 	}
 
+	uploadCompleted()
 	logrus.Tracef("Upload successful")
-	return nil
+
+	updatedPort := updatedUploadPort.Await()
+	if updatedPort == nil {
+		return nil, nil
+	}
+	return updatedPort.ToRPC(), nil
+}
+
+func detectUploadPort(
+	uploadCtx context.Context,
+	uploadPort *discovery.Port, watch <-chan *discovery.Event,
+	waitForUploadPort bool,
+	result f.Future[*discovery.Port],
+) {
+	log := logrus.WithField("task", "port_detection")
+	log.Tracef("Detecting new board port after upload")
+
+	candidate := uploadPort.Clone()
+	defer func() {
+		result.Send(candidate)
+	}()
+
+	// Ignore all events during the upload
+	for {
+		select {
+		case ev, ok := <-watch:
+			if !ok {
+				log.Error("Upload port detection failed, watcher closed")
+				return
+			}
+			if candidate != nil && ev.Type == "remove" && ev.Port.Equals(candidate) {
+				log.WithField("event", ev).Trace("User-specified port has been disconnected, forcing wait for upload port")
+				waitForUploadPort = true
+				candidate = nil
+			} else {
+				log.WithField("event", ev).Trace("Ignored watcher event before upload")
+			}
+			continue
+		case <-uploadCtx.Done():
+			// Upload completed, move to the next phase
+		}
+		break
+	}
+
+	// Pick the first port that is detected after the upload
+	timeout := time.After(5 * time.Second)
+	if !waitForUploadPort {
+		timeout = time.After(time.Second)
+	}
+	for {
+		select {
+		case ev, ok := <-watch:
+			if !ok {
+				log.Error("Upload port detection failed, watcher closed")
+				return
+			}
+			if candidate != nil && ev.Type == "remove" && candidate.Equals(ev.Port) {
+				log.WithField("event", ev).Trace("Candidate port is no longer available")
+				candidate = nil
+				if !waitForUploadPort {
+					waitForUploadPort = true
+					timeout = time.After(5 * time.Second)
+					log.Trace("User-specified port has been disconnected, now waiting for upload port, timeout extended by 5 seconds")
+				}
+				continue
+			}
+			if ev.Type != "add" {
+				log.WithField("event", ev).Trace("Ignored non-add event")
+				continue
+			}
+
+			portPriority := func(port *discovery.Port) int {
+				if port == nil {
+					return 0
+				}
+				prio := 0
+				if port.HardwareID == uploadPort.HardwareID {
+					prio += 1000
+				}
+				if port.Protocol == uploadPort.Protocol {
+					prio += 100
+				}
+				if port.Address == uploadPort.Address {
+					prio += 10
+				}
+				return prio
+			}
+			evPortPriority := portPriority(ev.Port)
+			candidatePriority := portPriority(candidate)
+			if evPortPriority <= candidatePriority {
+				log.WithField("event", ev).Tracef("New upload port candidate is worse than the current one (prio=%d)", evPortPriority)
+				continue
+			}
+			log.WithField("event", ev).Tracef("Found new upload port candidate (prio=%d)", evPortPriority)
+			candidate = ev.Port
+
+			// If the current candidate have the desired HW-ID return it quickly.
+			if candidate.HardwareID == ev.Port.HardwareID {
+				timeout = time.After(time.Second)
+				log.Trace("New candidate port match the desired HW ID, timeout reduced to 1 second.")
+				continue
+			}
+
+		case <-timeout:
+			log.WithField("selected_port", candidate).Trace("Timeout waiting for candidate port")
+			return
+		}
+	}
 }
 
 func runTool(recipeID string, props *properties.Map, outStream, errStream io.Writer, verbose bool, dryRun bool, toolEnv []string) error {
diff --git a/commands/upload/upload_test.go b/commands/upload/upload_test.go
index d3f69fd1baf..e1f87cd9832 100644
--- a/commands/upload/upload_test.go
+++ b/commands/upload/upload_test.go
@@ -184,7 +184,7 @@ func TestUploadPropertiesComposition(t *testing.T) {
 	testRunner := func(t *testing.T, test test, verboseVerify bool) {
 		outStream := &bytes.Buffer{}
 		errStream := &bytes.Buffer{}
-		err := runProgramAction(
+		_, err := runProgramAction(
 			pme,
 			nil,                     // sketch
 			"",                      // importFile
diff --git a/docs/UPGRADING.md b/docs/UPGRADING.md
index 31490513af2..d1821cf87fa 100644
--- a/docs/UPGRADING.md
+++ b/docs/UPGRADING.md
@@ -4,6 +4,58 @@ Here you can find a list of migration guides to handle breaking changes between
 
 ## 0.34.0
 
+### The gRPC `cc.arduino.cli.commands.v1.UploadRepsonse` command response has been changed.
+
+Previously the `UploadResponse` was used only to stream the tool output:
+
+```
+message UploadResponse {
+  // The output of the upload process.
+  bytes out_stream = 1;
+  // The error output of the upload process.
+  bytes err_stream = 2;
+}
+```
+
+Now the API logic has been clarified using the `oneof` clause and another field has been added providing an
+`UploadResult` message that is sent when a successful upload completes.
+
+```
+message UploadResponse {
+  oneof message {
+    // The output of the upload process.
+    bytes out_stream = 1;
+    // The error output of the upload process.
+    bytes err_stream = 2;
+    // The upload result
+    UploadResult result = 3;
+  }
+}
+
+message UploadResult {
+  // When a board requires a port disconnection to perform the upload, this
+  // field returns the port where the board reconnects after the upload.
+  Port updated_upload_port = 1;
+}
+```
+
+### golang API: method `github.com/arduino/arduino-cli/commands/upload.Upload` changed signature
+
+The `Upload` method signature has been changed from:
+
+```go
+func Upload(ctx context.Context, req *rpc.UploadRequest, outStream io.Writer, errStream io.Writer) error { ... }
+```
+
+to:
+
+```go
+func Upload(ctx context.Context, req *rpc.UploadRequest, outStream io.Writer, errStream io.Writer) (*rpc.UploadResult, error) { ... }
+```
+
+Now an `UploadResult` structure is returned together with the error. If you are not interested in the information
+contained in the structure you can safely ignore it.
+
 ### golang package `github.com/arduino/arduino-cli/inventory` removed from public API
 
 The package `inventory` is no more a public golang API.
diff --git a/internal/algorithms/channels.go b/internal/algorithms/channels.go
new file mode 100644
index 00000000000..982925322cb
--- /dev/null
+++ b/internal/algorithms/channels.go
@@ -0,0 +1,55 @@
+// This file is part of arduino-cli.
+//
+// Copyright 2023 ARDUINO SA (http://www.arduino.cc/)
+//
+// This software is released under the GNU General Public License version 3,
+// which covers the main part of arduino-cli.
+// The terms of this license can be found at:
+// https://www.gnu.org/licenses/gpl-3.0.en.html
+//
+// You can be released from the requirements of the above licenses by purchasing
+// a commercial license. Buying such a license is mandatory if you want to
+// modify or otherwise use the software for commercial activities involving the
+// Arduino software without disclosing the source code of your own applications.
+// To purchase a commercial license, send an email to license@arduino.cc.
+
+package f
+
+import "sync"
+
+// DiscardCh consumes all incoming messages from the given channel until it's closed.
+func DiscardCh[T any](ch <-chan T) {
+	for range ch {
+	}
+}
+
+// Future is an object that holds a result value. The value may be read and
+// written asynchronously.
+type Future[T any] interface {
+	Send(T)
+	Await() T
+}
+
+type future[T any] struct {
+	wg    sync.WaitGroup
+	value T
+}
+
+// NewFuture creates a new Future[T]
+func NewFuture[T any]() Future[T] {
+	res := &future[T]{}
+	res.wg.Add(1)
+	return res
+}
+
+// Send a result in the Future. Threads waiting for result will be unlocked.
+func (f *future[T]) Send(value T) {
+	f.value = value
+	f.wg.Done()
+}
+
+// Await for a result from the Future, blocks until a result is available.
+func (f *future[T]) Await() T {
+	f.wg.Wait()
+	return f.value
+}
diff --git a/internal/cli/compile/compile.go b/internal/cli/compile/compile.go
index b208cc79dfd..baa1dff5f89 100644
--- a/internal/cli/compile/compile.go
+++ b/internal/cli/compile/compile.go
@@ -236,6 +236,8 @@ func runCompileCommand(cmd *cobra.Command, args []string) {
 		DoNotExpandBuildProperties:    showProperties == arguments.ShowPropertiesUnexpanded,
 	}
 	compileRes, compileError := compile.Compile(context.Background(), compileRequest, stdOut, stdErr, nil)
+
+	var uploadRes *rpc.UploadResult
 	if compileError == nil && uploadAfterCompile {
 		userFieldRes, err := upload.SupportedUserFields(context.Background(), &rpc.SupportedUserFieldsRequest{
 			Instance: inst,
@@ -268,8 +270,10 @@ func runCompileCommand(cmd *cobra.Command, args []string) {
 			UserFields: fields,
 		}
 
-		if err := upload.Upload(context.Background(), uploadRequest, stdOut, stdErr); err != nil {
+		if res, err := upload.Upload(context.Background(), uploadRequest, stdOut, stdErr); err != nil {
 			feedback.Fatal(tr("Error during Upload: %v", err), feedback.ErrGeneric)
+		} else {
+			uploadRes = res
 		}
 	}
 
@@ -330,6 +334,7 @@ func runCompileCommand(cmd *cobra.Command, args []string) {
 		CompilerOut:        stdIO.Stdout,
 		CompilerErr:        stdIO.Stderr,
 		BuilderResult:      compileRes,
+		UploadResult:       uploadRes,
 		ProfileOut:         profileOut,
 		Success:            compileError == nil,
 		showPropertiesMode: showProperties,
@@ -375,6 +380,7 @@ type compileResult struct {
 	CompilerOut   string               `json:"compiler_out"`
 	CompilerErr   string               `json:"compiler_err"`
 	BuilderResult *rpc.CompileResponse `json:"builder_result"`
+	UploadResult  *rpc.UploadResult    `json:"upload_result"`
 	Success       bool                 `json:"success"`
 	ProfileOut    string               `json:"profile_out,omitempty"`
 	Error         string               `json:"error,omitempty"`
diff --git a/internal/cli/upload/upload.go b/internal/cli/upload/upload.go
index 739bb7d29e4..1fa91086ac0 100644
--- a/internal/cli/upload/upload.go
+++ b/internal/cli/upload/upload.go
@@ -168,8 +168,31 @@ func runUploadCommand(command *cobra.Command, args []string) {
 		DryRun:     dryRun,
 		UserFields: fields,
 	}
-	if err := upload.Upload(context.Background(), req, stdOut, stdErr); err != nil {
+	if res, err := upload.Upload(context.Background(), req, stdOut, stdErr); err != nil {
 		feedback.FatalError(err, feedback.ErrGeneric)
+	} else {
+		io := stdIOResult()
+		feedback.PrintResult(&uploadResult{
+			Stdout:            io.Stdout,
+			Stderr:            io.Stderr,
+			UpdatedUploadPort: res.UpdatedUploadPort,
+		})
 	}
-	feedback.PrintResult(stdIOResult())
+}
+
+type uploadResult struct {
+	Stdout            string    `json:"stdout"`
+	Stderr            string    `json:"stderr"`
+	UpdatedUploadPort *rpc.Port `json:"updated_upload_port,omitempty"`
+}
+
+func (r *uploadResult) Data() interface{} {
+	return r
+}
+
+func (r *uploadResult) String() string {
+	if r.UpdatedUploadPort == nil {
+		return ""
+	}
+	return tr("New upload port: %[1]s (%[2]s)", r.UpdatedUploadPort.Address, r.UpdatedUploadPort.Protocol)
 }
diff --git a/rpc/cc/arduino/cli/commands/v1/upload.pb.go b/rpc/cc/arduino/cli/commands/v1/upload.pb.go
index 50176927a47..0398a460ba1 100644
--- a/rpc/cc/arduino/cli/commands/v1/upload.pb.go
+++ b/rpc/cc/arduino/cli/commands/v1/upload.pb.go
@@ -192,10 +192,12 @@ type UploadResponse struct {
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
 
-	// The output of the upload process.
-	OutStream []byte `protobuf:"bytes,1,opt,name=out_stream,json=outStream,proto3" json:"out_stream,omitempty"`
-	// The error output of the upload process.
-	ErrStream []byte `protobuf:"bytes,2,opt,name=err_stream,json=errStream,proto3" json:"err_stream,omitempty"`
+	// Types that are assignable to Message:
+	//
+	//	*UploadResponse_OutStream
+	//	*UploadResponse_ErrStream
+	//	*UploadResponse_Result
+	Message isUploadResponse_Message `protobuf_oneof:"message"`
 }
 
 func (x *UploadResponse) Reset() {
@@ -230,20 +232,108 @@ func (*UploadResponse) Descriptor() ([]byte, []int) {
 	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{1}
 }
 
+func (m *UploadResponse) GetMessage() isUploadResponse_Message {
+	if m != nil {
+		return m.Message
+	}
+	return nil
+}
+
 func (x *UploadResponse) GetOutStream() []byte {
-	if x != nil {
+	if x, ok := x.GetMessage().(*UploadResponse_OutStream); ok {
 		return x.OutStream
 	}
 	return nil
 }
 
 func (x *UploadResponse) GetErrStream() []byte {
-	if x != nil {
+	if x, ok := x.GetMessage().(*UploadResponse_ErrStream); ok {
 		return x.ErrStream
 	}
 	return nil
 }
 
+func (x *UploadResponse) GetResult() *UploadResult {
+	if x, ok := x.GetMessage().(*UploadResponse_Result); ok {
+		return x.Result
+	}
+	return nil
+}
+
+type isUploadResponse_Message interface {
+	isUploadResponse_Message()
+}
+
+type UploadResponse_OutStream struct {
+	// The output of the upload process.
+	OutStream []byte `protobuf:"bytes,1,opt,name=out_stream,json=outStream,proto3,oneof"`
+}
+
+type UploadResponse_ErrStream struct {
+	// The error output of the upload process.
+	ErrStream []byte `protobuf:"bytes,2,opt,name=err_stream,json=errStream,proto3,oneof"`
+}
+
+type UploadResponse_Result struct {
+	// The upload result
+	Result *UploadResult `protobuf:"bytes,3,opt,name=result,proto3,oneof"`
+}
+
+func (*UploadResponse_OutStream) isUploadResponse_Message() {}
+
+func (*UploadResponse_ErrStream) isUploadResponse_Message() {}
+
+func (*UploadResponse_Result) isUploadResponse_Message() {}
+
+type UploadResult struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	// When a board requires a port disconnection to perform the upload, this
+	// field returns the port where the board reconnects after the upload.
+	UpdatedUploadPort *Port `protobuf:"bytes,1,opt,name=updated_upload_port,json=updatedUploadPort,proto3" json:"updated_upload_port,omitempty"`
+}
+
+func (x *UploadResult) Reset() {
+	*x = UploadResult{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[2]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *UploadResult) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*UploadResult) ProtoMessage() {}
+
+func (x *UploadResult) ProtoReflect() protoreflect.Message {
+	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[2]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use UploadResult.ProtoReflect.Descriptor instead.
+func (*UploadResult) Descriptor() ([]byte, []int) {
+	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{2}
+}
+
+func (x *UploadResult) GetUpdatedUploadPort() *Port {
+	if x != nil {
+		return x.UpdatedUploadPort
+	}
+	return nil
+}
+
 type ProgrammerIsRequiredForUploadError struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
@@ -253,7 +343,7 @@ type ProgrammerIsRequiredForUploadError struct {
 func (x *ProgrammerIsRequiredForUploadError) Reset() {
 	*x = ProgrammerIsRequiredForUploadError{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[2]
+		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[3]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -266,7 +356,7 @@ func (x *ProgrammerIsRequiredForUploadError) String() string {
 func (*ProgrammerIsRequiredForUploadError) ProtoMessage() {}
 
 func (x *ProgrammerIsRequiredForUploadError) ProtoReflect() protoreflect.Message {
-	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[2]
+	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[3]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -279,7 +369,7 @@ func (x *ProgrammerIsRequiredForUploadError) ProtoReflect() protoreflect.Message
 
 // Deprecated: Use ProgrammerIsRequiredForUploadError.ProtoReflect.Descriptor instead.
 func (*ProgrammerIsRequiredForUploadError) Descriptor() ([]byte, []int) {
-	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{2}
+	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{3}
 }
 
 type UploadUsingProgrammerRequest struct {
@@ -326,7 +416,7 @@ type UploadUsingProgrammerRequest struct {
 func (x *UploadUsingProgrammerRequest) Reset() {
 	*x = UploadUsingProgrammerRequest{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[3]
+		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[4]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -339,7 +429,7 @@ func (x *UploadUsingProgrammerRequest) String() string {
 func (*UploadUsingProgrammerRequest) ProtoMessage() {}
 
 func (x *UploadUsingProgrammerRequest) ProtoReflect() protoreflect.Message {
-	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[3]
+	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[4]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -352,7 +442,7 @@ func (x *UploadUsingProgrammerRequest) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use UploadUsingProgrammerRequest.ProtoReflect.Descriptor instead.
 func (*UploadUsingProgrammerRequest) Descriptor() ([]byte, []int) {
-	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{3}
+	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{4}
 }
 
 func (x *UploadUsingProgrammerRequest) GetInstance() *Instance {
@@ -446,7 +536,7 @@ type UploadUsingProgrammerResponse struct {
 func (x *UploadUsingProgrammerResponse) Reset() {
 	*x = UploadUsingProgrammerResponse{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[4]
+		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[5]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -459,7 +549,7 @@ func (x *UploadUsingProgrammerResponse) String() string {
 func (*UploadUsingProgrammerResponse) ProtoMessage() {}
 
 func (x *UploadUsingProgrammerResponse) ProtoReflect() protoreflect.Message {
-	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[4]
+	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[5]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -472,7 +562,7 @@ func (x *UploadUsingProgrammerResponse) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use UploadUsingProgrammerResponse.ProtoReflect.Descriptor instead.
 func (*UploadUsingProgrammerResponse) Descriptor() ([]byte, []int) {
-	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{4}
+	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{5}
 }
 
 func (x *UploadUsingProgrammerResponse) GetOutStream() []byte {
@@ -521,7 +611,7 @@ type BurnBootloaderRequest struct {
 func (x *BurnBootloaderRequest) Reset() {
 	*x = BurnBootloaderRequest{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[5]
+		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[6]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -534,7 +624,7 @@ func (x *BurnBootloaderRequest) String() string {
 func (*BurnBootloaderRequest) ProtoMessage() {}
 
 func (x *BurnBootloaderRequest) ProtoReflect() protoreflect.Message {
-	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[5]
+	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[6]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -547,7 +637,7 @@ func (x *BurnBootloaderRequest) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use BurnBootloaderRequest.ProtoReflect.Descriptor instead.
 func (*BurnBootloaderRequest) Descriptor() ([]byte, []int) {
-	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{5}
+	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{6}
 }
 
 func (x *BurnBootloaderRequest) GetInstance() *Instance {
@@ -620,7 +710,7 @@ type BurnBootloaderResponse struct {
 func (x *BurnBootloaderResponse) Reset() {
 	*x = BurnBootloaderResponse{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[6]
+		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[7]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -633,7 +723,7 @@ func (x *BurnBootloaderResponse) String() string {
 func (*BurnBootloaderResponse) ProtoMessage() {}
 
 func (x *BurnBootloaderResponse) ProtoReflect() protoreflect.Message {
-	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[6]
+	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[7]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -646,7 +736,7 @@ func (x *BurnBootloaderResponse) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use BurnBootloaderResponse.ProtoReflect.Descriptor instead.
 func (*BurnBootloaderResponse) Descriptor() ([]byte, []int) {
-	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{6}
+	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{7}
 }
 
 func (x *BurnBootloaderResponse) GetOutStream() []byte {
@@ -675,7 +765,7 @@ type ListProgrammersAvailableForUploadRequest struct {
 func (x *ListProgrammersAvailableForUploadRequest) Reset() {
 	*x = ListProgrammersAvailableForUploadRequest{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[7]
+		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[8]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -688,7 +778,7 @@ func (x *ListProgrammersAvailableForUploadRequest) String() string {
 func (*ListProgrammersAvailableForUploadRequest) ProtoMessage() {}
 
 func (x *ListProgrammersAvailableForUploadRequest) ProtoReflect() protoreflect.Message {
-	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[7]
+	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[8]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -701,7 +791,7 @@ func (x *ListProgrammersAvailableForUploadRequest) ProtoReflect() protoreflect.M
 
 // Deprecated: Use ListProgrammersAvailableForUploadRequest.ProtoReflect.Descriptor instead.
 func (*ListProgrammersAvailableForUploadRequest) Descriptor() ([]byte, []int) {
-	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{7}
+	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{8}
 }
 
 func (x *ListProgrammersAvailableForUploadRequest) GetInstance() *Instance {
@@ -729,7 +819,7 @@ type ListProgrammersAvailableForUploadResponse struct {
 func (x *ListProgrammersAvailableForUploadResponse) Reset() {
 	*x = ListProgrammersAvailableForUploadResponse{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[8]
+		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[9]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -742,7 +832,7 @@ func (x *ListProgrammersAvailableForUploadResponse) String() string {
 func (*ListProgrammersAvailableForUploadResponse) ProtoMessage() {}
 
 func (x *ListProgrammersAvailableForUploadResponse) ProtoReflect() protoreflect.Message {
-	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[8]
+	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[9]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -755,7 +845,7 @@ func (x *ListProgrammersAvailableForUploadResponse) ProtoReflect() protoreflect.
 
 // Deprecated: Use ListProgrammersAvailableForUploadResponse.ProtoReflect.Descriptor instead.
 func (*ListProgrammersAvailableForUploadResponse) Descriptor() ([]byte, []int) {
-	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{8}
+	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{9}
 }
 
 func (x *ListProgrammersAvailableForUploadResponse) GetProgrammers() []*Programmer {
@@ -781,7 +871,7 @@ type SupportedUserFieldsRequest struct {
 func (x *SupportedUserFieldsRequest) Reset() {
 	*x = SupportedUserFieldsRequest{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[9]
+		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[10]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -794,7 +884,7 @@ func (x *SupportedUserFieldsRequest) String() string {
 func (*SupportedUserFieldsRequest) ProtoMessage() {}
 
 func (x *SupportedUserFieldsRequest) ProtoReflect() protoreflect.Message {
-	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[9]
+	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[10]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -807,7 +897,7 @@ func (x *SupportedUserFieldsRequest) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use SupportedUserFieldsRequest.ProtoReflect.Descriptor instead.
 func (*SupportedUserFieldsRequest) Descriptor() ([]byte, []int) {
-	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{9}
+	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{10}
 }
 
 func (x *SupportedUserFieldsRequest) GetInstance() *Instance {
@@ -850,7 +940,7 @@ type UserField struct {
 func (x *UserField) Reset() {
 	*x = UserField{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[10]
+		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[11]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -863,7 +953,7 @@ func (x *UserField) String() string {
 func (*UserField) ProtoMessage() {}
 
 func (x *UserField) ProtoReflect() protoreflect.Message {
-	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[10]
+	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[11]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -876,7 +966,7 @@ func (x *UserField) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use UserField.ProtoReflect.Descriptor instead.
 func (*UserField) Descriptor() ([]byte, []int) {
-	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{10}
+	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{11}
 }
 
 func (x *UserField) GetToolId() string {
@@ -920,7 +1010,7 @@ type SupportedUserFieldsResponse struct {
 func (x *SupportedUserFieldsResponse) Reset() {
 	*x = SupportedUserFieldsResponse{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[11]
+		mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[12]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -933,7 +1023,7 @@ func (x *SupportedUserFieldsResponse) String() string {
 func (*SupportedUserFieldsResponse) ProtoMessage() {}
 
 func (x *SupportedUserFieldsResponse) ProtoReflect() protoreflect.Message {
-	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[11]
+	mi := &file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[12]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -946,7 +1036,7 @@ func (x *SupportedUserFieldsResponse) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use SupportedUserFieldsResponse.ProtoReflect.Descriptor instead.
 func (*SupportedUserFieldsResponse) Descriptor() ([]byte, []int) {
-	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{11}
+	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP(), []int{12}
 }
 
 func (x *SupportedUserFieldsResponse) GetUserFields() []*UserField {
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 }
 
 var (
@@ -1138,46 +1239,49 @@ func file_cc_arduino_cli_commands_v1_upload_proto_rawDescGZIP() []byte {
 	return file_cc_arduino_cli_commands_v1_upload_proto_rawDescData
 }
 
-var file_cc_arduino_cli_commands_v1_upload_proto_msgTypes = make([]protoimpl.MessageInfo, 15)
+var file_cc_arduino_cli_commands_v1_upload_proto_msgTypes = make([]protoimpl.MessageInfo, 16)
 var file_cc_arduino_cli_commands_v1_upload_proto_goTypes = []interface{}{
 	(*UploadRequest)(nil),                             // 0: cc.arduino.cli.commands.v1.UploadRequest
 	(*UploadResponse)(nil),                            // 1: cc.arduino.cli.commands.v1.UploadResponse
-	(*ProgrammerIsRequiredForUploadError)(nil),        // 2: cc.arduino.cli.commands.v1.ProgrammerIsRequiredForUploadError
-	(*UploadUsingProgrammerRequest)(nil),              // 3: cc.arduino.cli.commands.v1.UploadUsingProgrammerRequest
-	(*UploadUsingProgrammerResponse)(nil),             // 4: cc.arduino.cli.commands.v1.UploadUsingProgrammerResponse
-	(*BurnBootloaderRequest)(nil),                     // 5: cc.arduino.cli.commands.v1.BurnBootloaderRequest
-	(*BurnBootloaderResponse)(nil),                    // 6: cc.arduino.cli.commands.v1.BurnBootloaderResponse
-	(*ListProgrammersAvailableForUploadRequest)(nil),  // 7: cc.arduino.cli.commands.v1.ListProgrammersAvailableForUploadRequest
-	(*ListProgrammersAvailableForUploadResponse)(nil), // 8: cc.arduino.cli.commands.v1.ListProgrammersAvailableForUploadResponse
-	(*SupportedUserFieldsRequest)(nil),                // 9: cc.arduino.cli.commands.v1.SupportedUserFieldsRequest
-	(*UserField)(nil),                                 // 10: cc.arduino.cli.commands.v1.UserField
-	(*SupportedUserFieldsResponse)(nil),               // 11: cc.arduino.cli.commands.v1.SupportedUserFieldsResponse
-	nil,                                               // 12: cc.arduino.cli.commands.v1.UploadRequest.UserFieldsEntry
-	nil,                                               // 13: cc.arduino.cli.commands.v1.UploadUsingProgrammerRequest.UserFieldsEntry
-	nil,                                               // 14: cc.arduino.cli.commands.v1.BurnBootloaderRequest.UserFieldsEntry
-	(*Instance)(nil),                                  // 15: cc.arduino.cli.commands.v1.Instance
-	(*Port)(nil),                                      // 16: cc.arduino.cli.commands.v1.Port
-	(*Programmer)(nil),                                // 17: cc.arduino.cli.commands.v1.Programmer
+	(*UploadResult)(nil),                              // 2: cc.arduino.cli.commands.v1.UploadResult
+	(*ProgrammerIsRequiredForUploadError)(nil),        // 3: cc.arduino.cli.commands.v1.ProgrammerIsRequiredForUploadError
+	(*UploadUsingProgrammerRequest)(nil),              // 4: cc.arduino.cli.commands.v1.UploadUsingProgrammerRequest
+	(*UploadUsingProgrammerResponse)(nil),             // 5: cc.arduino.cli.commands.v1.UploadUsingProgrammerResponse
+	(*BurnBootloaderRequest)(nil),                     // 6: cc.arduino.cli.commands.v1.BurnBootloaderRequest
+	(*BurnBootloaderResponse)(nil),                    // 7: cc.arduino.cli.commands.v1.BurnBootloaderResponse
+	(*ListProgrammersAvailableForUploadRequest)(nil),  // 8: cc.arduino.cli.commands.v1.ListProgrammersAvailableForUploadRequest
+	(*ListProgrammersAvailableForUploadResponse)(nil), // 9: cc.arduino.cli.commands.v1.ListProgrammersAvailableForUploadResponse
+	(*SupportedUserFieldsRequest)(nil),                // 10: cc.arduino.cli.commands.v1.SupportedUserFieldsRequest
+	(*UserField)(nil),                                 // 11: cc.arduino.cli.commands.v1.UserField
+	(*SupportedUserFieldsResponse)(nil),               // 12: cc.arduino.cli.commands.v1.SupportedUserFieldsResponse
+	nil,                                               // 13: cc.arduino.cli.commands.v1.UploadRequest.UserFieldsEntry
+	nil,                                               // 14: cc.arduino.cli.commands.v1.UploadUsingProgrammerRequest.UserFieldsEntry
+	nil,                                               // 15: cc.arduino.cli.commands.v1.BurnBootloaderRequest.UserFieldsEntry
+	(*Instance)(nil),                                  // 16: cc.arduino.cli.commands.v1.Instance
+	(*Port)(nil),                                      // 17: cc.arduino.cli.commands.v1.Port
+	(*Programmer)(nil),                                // 18: cc.arduino.cli.commands.v1.Programmer
 }
 var file_cc_arduino_cli_commands_v1_upload_proto_depIdxs = []int32{
-	15, // 0: cc.arduino.cli.commands.v1.UploadRequest.instance:type_name -> cc.arduino.cli.commands.v1.Instance
-	16, // 1: cc.arduino.cli.commands.v1.UploadRequest.port:type_name -> cc.arduino.cli.commands.v1.Port
-	12, // 2: cc.arduino.cli.commands.v1.UploadRequest.user_fields:type_name -> cc.arduino.cli.commands.v1.UploadRequest.UserFieldsEntry
-	15, // 3: cc.arduino.cli.commands.v1.UploadUsingProgrammerRequest.instance:type_name -> cc.arduino.cli.commands.v1.Instance
-	16, // 4: cc.arduino.cli.commands.v1.UploadUsingProgrammerRequest.port:type_name -> cc.arduino.cli.commands.v1.Port
-	13, // 5: cc.arduino.cli.commands.v1.UploadUsingProgrammerRequest.user_fields:type_name -> cc.arduino.cli.commands.v1.UploadUsingProgrammerRequest.UserFieldsEntry
-	15, // 6: cc.arduino.cli.commands.v1.BurnBootloaderRequest.instance:type_name -> cc.arduino.cli.commands.v1.Instance
-	16, // 7: cc.arduino.cli.commands.v1.BurnBootloaderRequest.port:type_name -> cc.arduino.cli.commands.v1.Port
-	14, // 8: cc.arduino.cli.commands.v1.BurnBootloaderRequest.user_fields:type_name -> cc.arduino.cli.commands.v1.BurnBootloaderRequest.UserFieldsEntry
-	15, // 9: cc.arduino.cli.commands.v1.ListProgrammersAvailableForUploadRequest.instance:type_name -> cc.arduino.cli.commands.v1.Instance
-	17, // 10: cc.arduino.cli.commands.v1.ListProgrammersAvailableForUploadResponse.programmers:type_name -> cc.arduino.cli.commands.v1.Programmer
-	15, // 11: cc.arduino.cli.commands.v1.SupportedUserFieldsRequest.instance:type_name -> cc.arduino.cli.commands.v1.Instance
-	10, // 12: cc.arduino.cli.commands.v1.SupportedUserFieldsResponse.user_fields:type_name -> cc.arduino.cli.commands.v1.UserField
-	13, // [13:13] is the sub-list for method output_type
-	13, // [13:13] is the sub-list for method input_type
-	13, // [13:13] is the sub-list for extension type_name
-	13, // [13:13] is the sub-list for extension extendee
-	0,  // [0:13] is the sub-list for field type_name
+	16, // 0: cc.arduino.cli.commands.v1.UploadRequest.instance:type_name -> cc.arduino.cli.commands.v1.Instance
+	17, // 1: cc.arduino.cli.commands.v1.UploadRequest.port:type_name -> cc.arduino.cli.commands.v1.Port
+	13, // 2: cc.arduino.cli.commands.v1.UploadRequest.user_fields:type_name -> cc.arduino.cli.commands.v1.UploadRequest.UserFieldsEntry
+	2,  // 3: cc.arduino.cli.commands.v1.UploadResponse.result:type_name -> cc.arduino.cli.commands.v1.UploadResult
+	17, // 4: cc.arduino.cli.commands.v1.UploadResult.updated_upload_port:type_name -> cc.arduino.cli.commands.v1.Port
+	16, // 5: cc.arduino.cli.commands.v1.UploadUsingProgrammerRequest.instance:type_name -> cc.arduino.cli.commands.v1.Instance
+	17, // 6: cc.arduino.cli.commands.v1.UploadUsingProgrammerRequest.port:type_name -> cc.arduino.cli.commands.v1.Port
+	14, // 7: cc.arduino.cli.commands.v1.UploadUsingProgrammerRequest.user_fields:type_name -> cc.arduino.cli.commands.v1.UploadUsingProgrammerRequest.UserFieldsEntry
+	16, // 8: cc.arduino.cli.commands.v1.BurnBootloaderRequest.instance:type_name -> cc.arduino.cli.commands.v1.Instance
+	17, // 9: cc.arduino.cli.commands.v1.BurnBootloaderRequest.port:type_name -> cc.arduino.cli.commands.v1.Port
+	15, // 10: cc.arduino.cli.commands.v1.BurnBootloaderRequest.user_fields:type_name -> cc.arduino.cli.commands.v1.BurnBootloaderRequest.UserFieldsEntry
+	16, // 11: cc.arduino.cli.commands.v1.ListProgrammersAvailableForUploadRequest.instance:type_name -> cc.arduino.cli.commands.v1.Instance
+	18, // 12: cc.arduino.cli.commands.v1.ListProgrammersAvailableForUploadResponse.programmers:type_name -> cc.arduino.cli.commands.v1.Programmer
+	16, // 13: cc.arduino.cli.commands.v1.SupportedUserFieldsRequest.instance:type_name -> cc.arduino.cli.commands.v1.Instance
+	11, // 14: cc.arduino.cli.commands.v1.SupportedUserFieldsResponse.user_fields:type_name -> cc.arduino.cli.commands.v1.UserField
+	15, // [15:15] is the sub-list for method output_type
+	15, // [15:15] is the sub-list for method input_type
+	15, // [15:15] is the sub-list for extension type_name
+	15, // [15:15] is the sub-list for extension extendee
+	0,  // [0:15] is the sub-list for field type_name
 }
 
 func init() { file_cc_arduino_cli_commands_v1_upload_proto_init() }
@@ -1213,7 +1317,7 @@ func file_cc_arduino_cli_commands_v1_upload_proto_init() {
 			}
 		}
 		file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[2].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*ProgrammerIsRequiredForUploadError); i {
+			switch v := v.(*UploadResult); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -1225,7 +1329,7 @@ func file_cc_arduino_cli_commands_v1_upload_proto_init() {
 			}
 		}
 		file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[3].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*UploadUsingProgrammerRequest); i {
+			switch v := v.(*ProgrammerIsRequiredForUploadError); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -1237,7 +1341,7 @@ func file_cc_arduino_cli_commands_v1_upload_proto_init() {
 			}
 		}
 		file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[4].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*UploadUsingProgrammerResponse); i {
+			switch v := v.(*UploadUsingProgrammerRequest); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -1249,7 +1353,7 @@ func file_cc_arduino_cli_commands_v1_upload_proto_init() {
 			}
 		}
 		file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[5].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*BurnBootloaderRequest); i {
+			switch v := v.(*UploadUsingProgrammerResponse); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -1261,7 +1365,7 @@ func file_cc_arduino_cli_commands_v1_upload_proto_init() {
 			}
 		}
 		file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[6].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*BurnBootloaderResponse); i {
+			switch v := v.(*BurnBootloaderRequest); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -1273,7 +1377,7 @@ func file_cc_arduino_cli_commands_v1_upload_proto_init() {
 			}
 		}
 		file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[7].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*ListProgrammersAvailableForUploadRequest); i {
+			switch v := v.(*BurnBootloaderResponse); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -1285,7 +1389,7 @@ func file_cc_arduino_cli_commands_v1_upload_proto_init() {
 			}
 		}
 		file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[8].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*ListProgrammersAvailableForUploadResponse); i {
+			switch v := v.(*ListProgrammersAvailableForUploadRequest); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -1297,7 +1401,7 @@ func file_cc_arduino_cli_commands_v1_upload_proto_init() {
 			}
 		}
 		file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[9].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*SupportedUserFieldsRequest); i {
+			switch v := v.(*ListProgrammersAvailableForUploadResponse); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -1309,7 +1413,7 @@ func file_cc_arduino_cli_commands_v1_upload_proto_init() {
 			}
 		}
 		file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[10].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*UserField); i {
+			switch v := v.(*SupportedUserFieldsRequest); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -1321,6 +1425,18 @@ func file_cc_arduino_cli_commands_v1_upload_proto_init() {
 			}
 		}
 		file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[11].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*UserField); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[12].Exporter = func(v interface{}, i int) interface{} {
 			switch v := v.(*SupportedUserFieldsResponse); i {
 			case 0:
 				return &v.state
@@ -1333,13 +1449,18 @@ func file_cc_arduino_cli_commands_v1_upload_proto_init() {
 			}
 		}
 	}
+	file_cc_arduino_cli_commands_v1_upload_proto_msgTypes[1].OneofWrappers = []interface{}{
+		(*UploadResponse_OutStream)(nil),
+		(*UploadResponse_ErrStream)(nil),
+		(*UploadResponse_Result)(nil),
+	}
 	type x struct{}
 	out := protoimpl.TypeBuilder{
 		File: protoimpl.DescBuilder{
 			GoPackagePath: reflect.TypeOf(x{}).PkgPath(),
 			RawDescriptor: file_cc_arduino_cli_commands_v1_upload_proto_rawDesc,
 			NumEnums:      0,
-			NumMessages:   15,
+			NumMessages:   16,
 			NumExtensions: 0,
 			NumServices:   0,
 		},
diff --git a/rpc/cc/arduino/cli/commands/v1/upload.proto b/rpc/cc/arduino/cli/commands/v1/upload.proto
index d0aa108c0ef..8a2b6b0215d 100644
--- a/rpc/cc/arduino/cli/commands/v1/upload.proto
+++ b/rpc/cc/arduino/cli/commands/v1/upload.proto
@@ -62,10 +62,20 @@ message UploadRequest {
 }
 
 message UploadResponse {
-  // The output of the upload process.
-  bytes out_stream = 1;
-  // The error output of the upload process.
-  bytes err_stream = 2;
+  oneof message {
+    // The output of the upload process.
+    bytes out_stream = 1;
+    // The error output of the upload process.
+    bytes err_stream = 2;
+    // The upload result
+    UploadResult result = 3;
+  }
+}
+
+message UploadResult {
+  // When a board requires a port disconnection to perform the upload, this
+  // field returns the port where the board reconnects after the upload.
+  Port updated_upload_port = 1;
 }
 
 message ProgrammerIsRequiredForUploadError {}