diff --git a/cli/debug/debug.go b/cli/debug/debug.go
index d7ca207dd42..8e7c16b6134 100644
--- a/cli/debug/debug.go
+++ b/cli/debug/debug.go
@@ -17,18 +17,23 @@ package debug
 
 import (
 	"context"
+	"fmt"
 	"os"
 	"os/signal"
+	"sort"
 
 	"github.com/arduino/arduino-cli/cli/errorcodes"
 	"github.com/arduino/arduino-cli/cli/feedback"
 	"github.com/arduino/arduino-cli/cli/instance"
 	"github.com/arduino/arduino-cli/commands/debug"
-	rpc "github.com/arduino/arduino-cli/rpc/commands"
 	dbg "github.com/arduino/arduino-cli/rpc/debug"
+	"github.com/arduino/arduino-cli/table"
 	"github.com/arduino/go-paths-helper"
+	"github.com/arduino/go-properties-orderedmap"
+	"github.com/fatih/color"
 	"github.com/sirupsen/logrus"
 	"github.com/spf13/cobra"
+	"google.golang.org/grpc/status"
 )
 
 var (
@@ -38,6 +43,8 @@ var (
 	verify      bool
 	interpreter string
 	importDir   string
+	printInfo   bool
+	programmer  string
 )
 
 // NewCommand created a new `upload` command
@@ -46,15 +53,17 @@ func NewCommand() *cobra.Command {
 		Use:     "debug",
 		Short:   "Debug Arduino sketches.",
 		Long:    "Debug Arduino sketches. (this command opens an interactive gdb session)",
-		Example: "  " + os.Args[0] + " debug -b arduino:samd:mkr1000  /home/user/Arduino/MySketch",
+		Example: "  " + os.Args[0] + " debug -b arduino:samd:mkr1000 -P atmel_ice /home/user/Arduino/MySketch",
 		Args:    cobra.MaximumNArgs(1),
 		Run:     run,
 	}
 
 	debugCommand.Flags().StringVarP(&fqbn, "fqbn", "b", "", "Fully Qualified Board Name, e.g.: arduino:avr:uno")
 	debugCommand.Flags().StringVarP(&port, "port", "p", "", "Debug port, e.g.: COM10 or /dev/ttyACM0")
+	debugCommand.Flags().StringVarP(&programmer, "programmer", "P", "", "Programmer to use for debugging")
 	debugCommand.Flags().StringVar(&interpreter, "interpreter", "console", "Debug interpreter e.g.: console, mi, mi1, mi2, mi3")
 	debugCommand.Flags().StringVarP(&importDir, "input-dir", "", "", "Directory containing binaries for debug.")
+	debugCommand.Flags().BoolVarP(&printInfo, "info", "I", false, "Show metadata about the debug session instead of starting the debugger.")
 
 	return debugCommand
 }
@@ -72,20 +81,40 @@ func run(command *cobra.Command, args []string) {
 	}
 	sketchPath := initSketchPath(path)
 
-	// Intercept SIGINT and forward them to debug process
-	ctrlc := make(chan os.Signal, 1)
-	signal.Notify(ctrlc, os.Interrupt)
-
-	if _, err := debug.Debug(context.Background(), &dbg.DebugConfigReq{
-		Instance:    &rpc.Instance{Id: instance.GetId()},
+	debugConfigRequested := &dbg.DebugConfigReq{
+		Instance:    instance,
 		Fqbn:        fqbn,
 		SketchPath:  sketchPath.String(),
 		Port:        port,
 		Interpreter: interpreter,
 		ImportDir:   importDir,
-	}, os.Stdin, os.Stdout, ctrlc); err != nil {
-		feedback.Errorf("Error during Debug: %v", err)
-		os.Exit(errorcodes.ErrGeneric)
+		Programmer:  programmer,
+	}
+
+	if printInfo {
+
+		if res, err := debug.GetDebugConfig(context.Background(), debugConfigRequested); err != nil {
+			if status, ok := status.FromError(err); ok {
+				feedback.Errorf("Error getting Debug info: %v", status.Message())
+				errorcodes.ExitWithGrpcStatus(status)
+			}
+			feedback.Errorf("Error getting Debug info: %v", err)
+			os.Exit(errorcodes.ErrGeneric)
+		} else {
+			feedback.PrintResult(&debugInfoResult{res})
+		}
+
+	} else {
+
+		// Intercept SIGINT and forward them to debug process
+		ctrlc := make(chan os.Signal, 1)
+		signal.Notify(ctrlc, os.Interrupt)
+
+		if _, err := debug.Debug(context.Background(), debugConfigRequested, os.Stdin, os.Stdout, ctrlc); err != nil {
+			feedback.Errorf("Error during Debug: %v", err)
+			os.Exit(errorcodes.ErrGeneric)
+		}
+
 	}
 }
 
@@ -103,3 +132,42 @@ func initSketchPath(sketchPath *paths.Path) *paths.Path {
 	logrus.Infof("Reading sketch from dir: %s", wd)
 	return wd
 }
+
+type debugInfoResult struct {
+	info *dbg.GetDebugConfigResp
+}
+
+func (r *debugInfoResult) Data() interface{} {
+	return r.info
+}
+
+func (r *debugInfoResult) String() string {
+	t := table.New()
+	green := color.New(color.FgHiGreen)
+	dimGreen := color.New(color.FgGreen)
+	t.AddRow("Executable to debug", table.NewCell(r.info.GetExecutable(), green))
+	t.AddRow("Toolchain type", table.NewCell(r.info.GetToolchain(), green))
+	t.AddRow("Toolchain path", table.NewCell(r.info.GetToolchainPath(), dimGreen))
+	t.AddRow("Toolchain prefix", table.NewCell(r.info.GetToolchainPrefix(), dimGreen))
+	if len(r.info.GetToolchainConfiguration()) > 0 {
+		conf := properties.NewFromHashmap(r.info.GetToolchainConfiguration())
+		keys := conf.Keys()
+		sort.Strings(keys)
+		t.AddRow("Toolchain custom configurations")
+		for _, k := range keys {
+			t.AddRow(table.NewCell(" - "+k, dimGreen), table.NewCell(conf.Get(k), dimGreen))
+		}
+	}
+	t.AddRow("GDB Server type", table.NewCell(r.info.GetServer(), green))
+	t.AddRow("GDB Server path", table.NewCell(r.info.GetServerPath(), dimGreen))
+	if len(r.info.GetServerConfiguration()) > 0 {
+		conf := properties.NewFromHashmap(r.info.GetServerConfiguration())
+		keys := conf.Keys()
+		sort.Strings(keys)
+		t.AddRow(fmt.Sprintf("%s custom configurations", r.info.GetServer()))
+		for _, k := range keys {
+			t.AddRow(table.NewCell(" - "+k, dimGreen), table.NewCell(conf.Get(k), dimGreen))
+		}
+	}
+	return t.Render()
+}
diff --git a/cli/errorcodes/errorcodes.go b/cli/errorcodes/errorcodes.go
index 777967e9460..529aead1efd 100644
--- a/cli/errorcodes/errorcodes.go
+++ b/cli/errorcodes/errorcodes.go
@@ -15,6 +15,13 @@
 
 package errorcodes
 
+import (
+	"os"
+
+	"google.golang.org/grpc/codes"
+	"google.golang.org/grpc/status"
+)
+
 // Error codes to be used for os.Exit().
 const (
 	_          = iota // 0 is not a valid exit error code
@@ -29,3 +36,14 @@ const (
 	ErrCoreConfig
 	ErrBadArgument
 )
+
+// ExitWithGrpcStatus will terminate the current process by returing the correct
+// error code closest matching the gRPC status.
+func ExitWithGrpcStatus(s *status.Status) {
+	switch s.Code() {
+	case codes.Unimplemented:
+		os.Exit(ErrBadArgument)
+	default:
+		os.Exit(ErrGeneric)
+	}
+}
diff --git a/commands/daemon/debug.go b/commands/daemon/debug.go
index b3ecef435a7..88ea30eec9e 100644
--- a/commands/daemon/debug.go
+++ b/commands/daemon/debug.go
@@ -16,10 +16,12 @@
 package daemon
 
 import (
+	"context"
 	"os"
 
 	"github.com/arduino/arduino-cli/arduino/utils"
 	cmd "github.com/arduino/arduino-cli/commands/debug"
+	"github.com/arduino/arduino-cli/rpc/debug"
 	dbg "github.com/arduino/arduino-cli/rpc/debug"
 	"github.com/pkg/errors"
 )
@@ -64,3 +66,8 @@ func (s *DebugService) Debug(stream dbg.Debug_DebugServer) error {
 	}
 	return stream.Send(resp)
 }
+
+// GetDebugConfig return metadata about a debug session
+func (s *DebugService) GetDebugConfig(ctx context.Context, req *debug.DebugConfigReq) (*debug.GetDebugConfigResp, error) {
+	return cmd.GetDebugConfig(ctx, req)
+}
diff --git a/commands/debug/debug.go b/commands/debug/debug.go
index 3a51c10f041..b35cc0c6eb2 100644
--- a/commands/debug/debug.go
+++ b/commands/debug/debug.go
@@ -21,17 +21,14 @@ import (
 	"io"
 	"os"
 	"path/filepath"
-	"strings"
+	"runtime"
 	"time"
 
-	"github.com/arduino/arduino-cli/arduino/cores"
 	"github.com/arduino/arduino-cli/arduino/cores/packagemanager"
-	"github.com/arduino/arduino-cli/arduino/sketches"
 	"github.com/arduino/arduino-cli/commands"
 	"github.com/arduino/arduino-cli/executils"
 	dbg "github.com/arduino/arduino-cli/rpc/debug"
 	"github.com/arduino/go-paths-helper"
-	"github.com/arduino/go-properties-orderedmap"
 	"github.com/pkg/errors"
 	"github.com/sirupsen/logrus"
 )
@@ -44,17 +41,15 @@ import (
 // It also implements tool process lifecycle management
 func Debug(ctx context.Context, req *dbg.DebugConfigReq, inStream io.Reader, out io.Writer, interrupt <-chan os.Signal) (*dbg.DebugResp, error) {
 
-	// Get tool commandLine from core recipe
+	// Get debugging command line to run debugger
 	pm := commands.GetPackageManager(req.GetInstance().GetId())
 	commandLine, err := getCommandLine(req, pm)
 	if err != nil {
 		return nil, errors.Wrap(err, "Cannot get command line for tool")
 	}
 
-	// Transform every path to forward slashes (on Windows some tools further
-	// escapes the command line so the backslash "\" gets in the way).
-	for i, param := range commandLine {
-		commandLine[i] = filepath.ToSlash(param)
+	for i, arg := range commandLine {
+		fmt.Printf("%2d: %s\n", i, arg)
 	}
 
 	// Run Tool
@@ -115,130 +110,74 @@ func Debug(ctx context.Context, req *dbg.DebugConfigReq, inStream io.Reader, out
 
 // getCommandLine compose a debug command represented by a core recipe
 func getCommandLine(req *dbg.DebugConfigReq, pm *packagemanager.PackageManager) ([]string, error) {
-	if req.GetImportFile() != "" {
-		return nil, errors.New("the ImportFile parameter has been deprecated, use ImportDir instead")
-	}
-
-	// TODO: make a generic function to extract sketch from request
-	// and remove duplication in commands/compile.go
-	if req.GetSketchPath() == "" {
-		return nil, fmt.Errorf("missing sketchPath")
-	}
-	sketchPath := paths.New(req.GetSketchPath())
-	sketch, err := sketches.NewSketchFromPath(sketchPath)
+	debugInfo, err := getDebugProperties(req, pm)
 	if err != nil {
-		return nil, errors.Wrap(err, "opening sketch")
+		return nil, err
 	}
 
-	fqbnIn := req.GetFqbn()
-	if fqbnIn == "" && sketch != nil && sketch.Metadata != nil {
-		fqbnIn = sketch.Metadata.CPU.Fqbn
+	cmdArgs := []string{}
+	add := func(s string) { cmdArgs = append(cmdArgs, s) }
+
+	// Add path to GDB Client to command line
+	var gdbPath *paths.Path
+	switch debugInfo.GetToolchain() {
+	case "gcc":
+		gdbexecutable := debugInfo.ToolchainPrefix + "gdb"
+		if runtime.GOOS == "windows" {
+			gdbexecutable += ".exe"
+		}
+		gdbPath = paths.New(debugInfo.ToolchainPath).Join(gdbexecutable)
+	default:
+		return nil, errors.Errorf("unsupported toolchain '%s'", debugInfo.GetToolchain())
 	}
-	if fqbnIn == "" {
-		return nil, fmt.Errorf("no Fully Qualified Board Name provided")
+	add(gdbPath.String())
+
+	// Set GDB interpreter (default value should be "console")
+	gdbInterpreter := req.GetInterpreter()
+	if gdbInterpreter == "" {
+		gdbInterpreter = "console"
 	}
-	fqbn, err := cores.ParseFQBN(fqbnIn)
-	if err != nil {
-		return nil, errors.Wrap(err, "error parsing FQBN")
+	add("--interpreter=" + gdbInterpreter)
+	if gdbInterpreter != "console" {
+		add("-ex")
+		add("set pagination off")
 	}
 
-	// Find target board and board properties
-	_, _, board, boardProperties, _, err := pm.ResolveFQBN(fqbn)
-	if err != nil {
-		return nil, errors.Wrap(err, "error resolving FQBN")
-	}
+	// Add extra GDB execution commands
+	add("-ex")
+	add("set remotetimeout 5")
 
-	// Load programmer tool
-	toolName, have := boardProperties.GetOk("debug.tool")
-	if !have || toolName == "" {
-		return nil, fmt.Errorf("cannot get programmer tool: undefined 'debug.tool' property")
-	}
+	// Extract path to GDB Server
+	switch debugInfo.GetServer() {
+	case "openocd":
+		serverCmd := fmt.Sprintf(`target extended-remote | "%s"`, debugInfo.ServerPath)
 
-	var referencedPlatformRelease *cores.PlatformRelease
-	if split := strings.Split(toolName, ":"); len(split) > 2 {
-		return nil, fmt.Errorf("invalid 'debug.tool' property: %s", toolName)
-	} else if len(split) == 2 {
-		referencedPackageName := split[0]
-		toolName = split[1]
-		architecture := board.PlatformRelease.Platform.Architecture
-
-		if referencedPackage := pm.Packages[referencedPackageName]; referencedPackage == nil {
-			return nil, fmt.Errorf("required platform %s:%s not installed", referencedPackageName, architecture)
-		} else if referencedPlatform := referencedPackage.Platforms[architecture]; referencedPlatform == nil {
-			return nil, fmt.Errorf("required platform %s:%s not installed", referencedPackageName, architecture)
-		} else {
-			referencedPlatformRelease = pm.GetInstalledPlatformRelease(referencedPlatform)
+		if cfg := debugInfo.ServerConfiguration["scripts_dir"]; cfg != "" {
+			serverCmd += fmt.Sprintf(` -s "%s"`, cfg)
 		}
-	}
 
-	// Build configuration for debug
-	toolProperties := properties.NewMap()
-	if referencedPlatformRelease != nil {
-		toolProperties.Merge(referencedPlatformRelease.Properties)
-	}
-	toolProperties.Merge(board.PlatformRelease.Properties)
-	toolProperties.Merge(board.PlatformRelease.RuntimeProperties())
-	toolProperties.Merge(boardProperties)
-
-	requestedToolProperties := toolProperties.SubTree("tools." + toolName)
-	toolProperties.Merge(requestedToolProperties)
-	if requiredTools, err := pm.FindToolsRequiredForBoard(board); err == nil {
-		for _, requiredTool := range requiredTools {
-			logrus.WithField("tool", requiredTool).Info("Tool required for debug")
-			toolProperties.Merge(requiredTool.RuntimeProperties())
+		if script := debugInfo.ServerConfiguration["script"]; script != "" {
+			serverCmd += fmt.Sprintf(` --file "%s"`, script)
 		}
-	}
 
-	var importPath *paths.Path
-	if importDir := req.GetImportDir(); importDir != "" {
-		importPath = paths.New(importDir)
-	} else {
-		// TODO: Create a function to obtain importPath from sketch
-		importPath = sketch.FullPath
-		// Add FQBN (without configs part) to export path
-		fqbnSuffix := strings.Replace(fqbn.StringWithoutConfig(), ":", ".", -1)
-		importPath = importPath.Join("build").Join(fqbnSuffix)
-	}
-	if !importPath.Exist() {
-		return nil, fmt.Errorf("compiled sketch not found in %s", importPath)
-	}
-	if !importPath.IsDir() {
-		return nil, fmt.Errorf("expected compiled sketch in directory %s, but is a file instead", importPath)
-	}
-	toolProperties.SetPath("build.path", importPath)
-	toolProperties.Set("build.project_name", sketch.Name+".ino")
-
-	// Set debug port property
-	port := req.GetPort()
-	if port != "" {
-		toolProperties.Set("debug.port", port)
-		if strings.HasPrefix(port, "/dev/") {
-			toolProperties.Set("debug.port.file", port[5:])
-		} else {
-			toolProperties.Set("debug.port.file", port)
-		}
-	}
+		serverCmd += ` -c "gdb_port pipe"`
+		serverCmd += ` -c "telnet_port 0"`
+
+		add("-ex")
+		add(serverCmd)
 
-	// Set debugger interpreter (default value should be "console")
-	interpreter := req.GetInterpreter()
-	if interpreter != "" {
-		toolProperties.Set("interpreter", interpreter)
-	} else {
-		toolProperties.Set("interpreter", "console")
+	default:
+		return nil, errors.Errorf("unsupported gdb server '%s'", debugInfo.GetServer())
 	}
 
-	// Build recipe for tool
-	recipe := toolProperties.Get("debug.pattern")
+	// Add executable
+	add(debugInfo.Executable)
 
-	// REMOVEME: hotfix for samd core 1.8.5/1.8.6
-	if recipe == `"{path}/{cmd}" --interpreter=mi2 -ex "set pagination off" -ex 'target extended-remote | {tools.openocd.path}/{tools.openocd.cmd} -s "{tools.openocd.path}/share/openocd/scripts/" --file "{runtime.platform.path}/variants/{build.variant}/{build.openocdscript}" -c "gdb_port pipe" -c "telnet_port 0"' {build.path}/{build.project_name}.elf` {
-		recipe = `"{path}/{cmd}" --interpreter={interpreter} -ex "set remotetimeout 5" -ex "set pagination off" -ex 'target extended-remote | "{tools.openocd.path}/{tools.openocd.cmd}" -s "{tools.openocd.path}/share/openocd/scripts/" --file "{runtime.platform.path}/variants/{build.variant}/{build.openocdscript}" -c "gdb_port pipe" -c "telnet_port 0"' "{build.path}/{build.project_name}.elf"`
+	// Transform every path to forward slashes (on Windows some tools further
+	// escapes the command line so the backslash "\" gets in the way).
+	for i, param := range cmdArgs {
+		cmdArgs[i] = filepath.ToSlash(param)
 	}
 
-	cmdLine := toolProperties.ExpandPropsInString(recipe)
-	cmdArgs, err := properties.SplitQuotedString(cmdLine, `"'`, false)
-	if err != nil {
-		return nil, fmt.Errorf("invalid recipe '%s': %s", recipe, err)
-	}
 	return cmdArgs, nil
 }
diff --git a/commands/debug/debug_info.go b/commands/debug/debug_info.go
new file mode 100644
index 00000000000..faad0987458
--- /dev/null
+++ b/commands/debug/debug_info.go
@@ -0,0 +1,169 @@
+// This file is part of arduino-cli.
+//
+// Copyright 2020 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 debug
+
+import (
+	"context"
+	"fmt"
+	"strings"
+
+	"github.com/arduino/arduino-cli/arduino/cores"
+	"github.com/arduino/arduino-cli/arduino/cores/packagemanager"
+	"github.com/arduino/arduino-cli/arduino/sketches"
+	"github.com/arduino/arduino-cli/commands"
+	"github.com/arduino/arduino-cli/rpc/debug"
+	"github.com/arduino/go-paths-helper"
+	"github.com/arduino/go-properties-orderedmap"
+	"github.com/pkg/errors"
+	"github.com/sirupsen/logrus"
+	"google.golang.org/grpc/codes"
+	"google.golang.org/grpc/status"
+)
+
+// GetDebugConfig returns metadata to start debugging with the specified board
+func GetDebugConfig(ctx context.Context, req *debug.DebugConfigReq) (*debug.GetDebugConfigResp, error) {
+	pm := commands.GetPackageManager(req.GetInstance().GetId())
+
+	return getDebugProperties(req, pm)
+}
+
+func getDebugProperties(req *debug.DebugConfigReq, pm *packagemanager.PackageManager) (*debug.GetDebugConfigResp, error) {
+	// TODO: make a generic function to extract sketch from request
+	// and remove duplication in commands/compile.go
+	if req.GetSketchPath() == "" {
+		return nil, fmt.Errorf("missing sketchPath")
+	}
+	sketchPath := paths.New(req.GetSketchPath())
+	sketch, err := sketches.NewSketchFromPath(sketchPath)
+	if err != nil {
+		return nil, errors.Wrap(err, "opening sketch")
+	}
+
+	// XXX Remove this code duplication!!
+	fqbnIn := req.GetFqbn()
+	if fqbnIn == "" && sketch != nil && sketch.Metadata != nil {
+		fqbnIn = sketch.Metadata.CPU.Fqbn
+	}
+	if fqbnIn == "" {
+		return nil, fmt.Errorf("no Fully Qualified Board Name provided")
+	}
+	fqbn, err := cores.ParseFQBN(fqbnIn)
+	if err != nil {
+		return nil, errors.Wrap(err, "error parsing FQBN")
+	}
+
+	// Find target board and board properties
+	_, platformRelease, board, boardProperties, referencedPlatformRelease, err := pm.ResolveFQBN(fqbn)
+	if err != nil {
+		return nil, errors.Wrap(err, "error resolving FQBN")
+	}
+
+	// Build configuration for debug
+	toolProperties := properties.NewMap()
+	if referencedPlatformRelease != nil {
+		toolProperties.Merge(referencedPlatformRelease.Properties)
+	}
+	toolProperties.Merge(platformRelease.Properties)
+	toolProperties.Merge(platformRelease.RuntimeProperties())
+	toolProperties.Merge(boardProperties)
+
+	// HOTFIX: Remove me when the `arduino:samd` core is updated
+	if !toolProperties.ContainsKey("debug.executable") {
+		if platformRelease.String() == "arduino:samd@1.8.9" || platformRelease.String() == "arduino:samd@1.8.8" {
+			toolProperties.Set("debug.executable", "{build.path}/{build.project_name}.elf")
+			toolProperties.Set("debug.toolchain", "gcc")
+			toolProperties.Set("debug.toolchain.path", "{runtime.tools.arm-none-eabi-gcc-7-2017q4.path}/bin/")
+			toolProperties.Set("debug.toolchain.prefix", "arm-none-eabi-")
+			toolProperties.Set("debug.server", "openocd")
+			toolProperties.Set("debug.server.openocd.path", "{runtime.tools.openocd-0.10.0-arduino7.path}/bin/openocd")
+			toolProperties.Set("debug.server.openocd.scripts_dir", "{runtime.tools.openocd-0.10.0-arduino7.path}/share/openocd/scripts/")
+			toolProperties.Set("debug.server.openocd.script", "{runtime.platform.path}/variants/{build.variant}/{build.openocdscript}")
+		}
+	}
+
+	for _, tool := range pm.GetAllInstalledToolsReleases() {
+		toolProperties.Merge(tool.RuntimeProperties())
+	}
+	if requiredTools, err := pm.FindToolsRequiredForBoard(board); err == nil {
+		for _, requiredTool := range requiredTools {
+			logrus.WithField("tool", requiredTool).Info("Tool required for debug")
+			toolProperties.Merge(requiredTool.RuntimeProperties())
+		}
+	}
+
+	if req.GetProgrammer() != "" {
+		if p, ok := platformRelease.Programmers[req.GetProgrammer()]; ok {
+			toolProperties.Merge(p.Properties)
+		} else if refP, ok := referencedPlatformRelease.Programmers[req.GetProgrammer()]; ok {
+			toolProperties.Merge(refP.Properties)
+		} else {
+			return nil, fmt.Errorf("programmer '%s' not found", req.GetProgrammer())
+		}
+	}
+
+	var importPath *paths.Path
+	if importDir := req.GetImportDir(); importDir != "" {
+		importPath = paths.New(importDir)
+	} else {
+		// TODO: Create a function to obtain importPath from sketch
+		importPath = sketch.FullPath
+		// Add FQBN (without configs part) to export path
+		fqbnSuffix := strings.Replace(fqbn.StringWithoutConfig(), ":", ".", -1)
+		importPath = importPath.Join("build").Join(fqbnSuffix)
+	}
+	if !importPath.Exist() {
+		return nil, fmt.Errorf("compiled sketch not found in %s", importPath)
+	}
+	if !importPath.IsDir() {
+		return nil, fmt.Errorf("expected compiled sketch in directory %s, but is a file instead", importPath)
+	}
+	toolProperties.SetPath("build.path", importPath)
+	toolProperties.Set("build.project_name", sketch.Name+".ino")
+
+	// Set debug port property
+	port := req.GetPort()
+	if port != "" {
+		toolProperties.Set("debug.port", port)
+		if strings.HasPrefix(port, "/dev/") {
+			toolProperties.Set("debug.port.file", port[5:])
+		} else {
+			toolProperties.Set("debug.port.file", port)
+		}
+	}
+
+	// Extract and expand all debugging properties
+	debugProperties := properties.NewMap()
+	for k, v := range toolProperties.SubTree("debug").AsMap() {
+		debugProperties.Set(k, toolProperties.ExpandPropsInString(v))
+	}
+
+	if !debugProperties.ContainsKey("executable") {
+		return nil, status.Error(codes.Unimplemented, fmt.Sprintf("debugging not supported for board %s", req.GetFqbn()))
+	}
+
+	server := debugProperties.Get("server")
+	toolchain := debugProperties.Get("toolchain")
+	return &debug.GetDebugConfigResp{
+		Executable:             debugProperties.Get("executable"),
+		Server:                 server,
+		ServerPath:             debugProperties.Get("server." + server + ".path"),
+		ServerConfiguration:    debugProperties.SubTree("server." + server).AsMap(),
+		Toolchain:              toolchain,
+		ToolchainPath:          debugProperties.Get("toolchain.path"),
+		ToolchainPrefix:        debugProperties.Get("toolchain.prefix"),
+		ToolchainConfiguration: debugProperties.SubTree("toolchain." + toolchain).AsMap(),
+	}, nil
+}
diff --git a/commands/debug/debug_test.go b/commands/debug/debug_test.go
index 8d0fd57ad7f..7712ad455a9 100644
--- a/commands/debug/debug_test.go
+++ b/commands/debug/debug_test.go
@@ -53,12 +53,12 @@ func TestGetCommandLine(t *testing.T) {
 		SketchPath: sketchPath.String(),
 	}
 
-	goldCommand := fmt.Sprintf("%s/arduino-test/tools/arm-none-eabi-gcc/7-2017q4/bin//arm-none-eabi-gdb%s", dataDir, toolExtension) +
-		" --interpreter=console -ex target extended-remote |" +
-		fmt.Sprintf(" %s/arduino-test/tools/openocd/0.10.0-arduino7/bin/openocd%s", dataDir, toolExtension) +
+	goldCommand := fmt.Sprintf("%s/arduino-test/tools/arm-none-eabi-gcc/7-2017q4/bin/arm-none-eabi-gdb%s", dataDir, toolExtension) +
+		" --interpreter=console -ex set remotetimeout 5 -ex target extended-remote |" +
+		fmt.Sprintf(" \"%s/arduino-test/tools/openocd/0.10.0-arduino7/bin/openocd%s\"", dataDir, toolExtension) +
 		fmt.Sprintf(" -s \"%s/arduino-test/tools/openocd/0.10.0-arduino7/share/openocd/scripts/\"", dataDir) +
 		fmt.Sprintf(" --file \"%s/arduino-test/samd/variants/arduino_zero/openocd_scripts/arduino_zero.cfg\"", customHardware) +
-		fmt.Sprintf(" -c \"gdb_port pipe\" -c \"telnet_port 0\" -c init -c halt %s/build/arduino-test.samd.arduino_zero_edbg/hello.ino.elf", sketchPath)
+		fmt.Sprintf(" -c \"gdb_port pipe\" -c \"telnet_port 0\" %s/build/arduino-test.samd.arduino_zero_edbg/hello.ino.elf", sketchPath)
 
 	command, err := getCommandLine(req, pm)
 	require.Nil(t, err)
@@ -74,12 +74,12 @@ func TestGetCommandLine(t *testing.T) {
 		Interpreter: "mi1",
 	}
 
-	goldCommand2 := fmt.Sprintf("%s/arduino-test/tools/arm-none-eabi-gcc/7-2017q4/bin//arm-none-eabi-gdb%s", dataDir, toolExtension) +
-		" --interpreter=mi1 -ex target extended-remote |" +
-		fmt.Sprintf(" %s/arduino-test/tools/openocd/0.10.0-arduino7/bin/openocd%s", dataDir, toolExtension) +
+	goldCommand2 := fmt.Sprintf("%s/arduino-test/tools/arm-none-eabi-gcc/7-2017q4/bin/arm-none-eabi-gdb%s", dataDir, toolExtension) +
+		" --interpreter=mi1 -ex set pagination off -ex set remotetimeout 5 -ex target extended-remote |" +
+		fmt.Sprintf(" \"%s/arduino-test/tools/openocd/0.10.0-arduino7/bin/openocd%s\"", dataDir, toolExtension) +
 		fmt.Sprintf(" -s \"%s/arduino-test/tools/openocd/0.10.0-arduino7/share/openocd/scripts/\"", dataDir) +
 		fmt.Sprintf(" --file \"%s/arduino-test/samd/variants/mkr1000/openocd_scripts/arduino_zero.cfg\"", customHardware) +
-		fmt.Sprintf(" -c \"gdb_port pipe\" -c \"telnet_port 0\" -c init -c halt %s/build/arduino-test.samd.mkr1000/hello.ino.elf", sketchPath)
+		fmt.Sprintf(" -c \"gdb_port pipe\" -c \"telnet_port 0\" %s/build/arduino-test.samd.mkr1000/hello.ino.elf", sketchPath)
 
 	command2, err := getCommandLine(req2, pm)
 	assert.Nil(t, err)
diff --git a/commands/debug/testdata/custom_hardware/arduino-test/samd/boards.txt b/commands/debug/testdata/custom_hardware/arduino-test/samd/boards.txt
index 033fb584fa7..ea2b1c6d3ff 100644
--- a/commands/debug/testdata/custom_hardware/arduino-test/samd/boards.txt
+++ b/commands/debug/testdata/custom_hardware/arduino-test/samd/boards.txt
@@ -20,7 +20,6 @@ arduino_zero_edbg.name=Arduino Zero (Programming Port)
 arduino_zero_edbg.vid.0=0x03eb
 arduino_zero_edbg.pid.0=0x2157
 
-arduino_zero_edbg.debug.tool=gdb-openocd
 arduino_zero_edbg.upload.tool=openocd
 arduino_zero_edbg.upload.protocol=sam-ba
 arduino_zero_edbg.upload.maximum_size=262144
@@ -55,7 +54,6 @@ mkr1000.pid.2=0x824e
 mkr1000.vid.3=0x2341
 mkr1000.pid.3=0x024e
 
-mkr1000.debug.tool=gdb-openocd
 mkr1000.upload.tool=bossac
 mkr1000.upload.protocol=sam-ba
 mkr1000.upload.maximum_size=262144
diff --git a/commands/debug/testdata/custom_hardware/arduino-test/samd/platform.txt b/commands/debug/testdata/custom_hardware/arduino-test/samd/platform.txt
index 5e61eb4db44..13a012118e8 100644
--- a/commands/debug/testdata/custom_hardware/arduino-test/samd/platform.txt
+++ b/commands/debug/testdata/custom_hardware/arduino-test/samd/platform.txt
@@ -113,6 +113,22 @@ recipe.output.save_file={build.project_name}.{build.variant}.{build.preferred_ou
 recipe.size.pattern="{compiler.path}{compiler.size.cmd}" -A "{build.path}/{build.project_name}.elf"
 recipe.size.regex=\.text\s+([0-9]+).*
 
+
+# Debugger configuration (general options)
+# ----------------------------------------
+# EXPERIMENTAL feature:
+#  - this is alpha and may be subject to change without notice
+debug.executable={build.path}/{build.project_name}.elf
+debug.toolchain=gcc
+debug.toolchain.path={runtime.tools.arm-none-eabi-gcc-7-2017q4.path}/bin/
+debug.toolchain.prefix=arm-none-eabi-
+debug.server=openocd
+debug.server.openocd.path={runtime.tools.openocd-0.10.0-arduino7.path}/bin/openocd
+debug.server.openocd.path.windows={runtime.tools.openocd-0.10.0-arduino7.path}/bin/openocd.exe
+debug.server.openocd.scripts_dir={runtime.tools.openocd-0.10.0-arduino7.path}/share/openocd/scripts/
+debug.server.openocd.script={runtime.platform.path}/variants/{build.variant}/{build.openocdscript}
+
+
 # Upload/Debug tools
 # ------------------
 
@@ -219,13 +235,3 @@ tools.openocd-withbootsize.erase.pattern=
 tools.openocd-withbootsize.bootloader.params.verbose=-d2
 tools.openocd-withbootsize.bootloader.params.quiet=-d0
 tools.openocd-withbootsize.bootloader.pattern="{path}/{cmd}" {bootloader.verbose} -s "{path}/share/openocd/scripts/" -f "{runtime.platform.path}/variants/{build.variant}/{build.openocdscript}" -c "telnet_port disabled; init; halt; at91samd bootloader 0; program {{runtime.platform.path}/bootloaders/{bootloader.file}} verify reset; shutdown"
-
-#
-# GDB (Debugger)
-#
-
-tools.gdb-openocd.path={runtime.tools.arm-none-eabi-gcc-7-2017q4.path}/bin/
-tools.gdb-openocd.cmd=arm-none-eabi-gdb
-tools.gdb-openocd.cmd.windows=arm-none-eabi-gdb.exe
-tools.gdb-openocd.interpreter=console
-tools.gdb-openocd.debug.pattern="{path}/{cmd}" --interpreter={interpreter}  -ex 'target extended-remote | {tools.openocd.path}/{tools.openocd.cmd} -s "{tools.openocd.path}/share/openocd/scripts/" --file "{runtime.platform.path}/variants/{build.variant}/{build.openocdscript}" -c "gdb_port pipe" -c "telnet_port 0" -c init -c halt' {build.path}/{build.project_name}.elf
diff --git a/rpc/debug/debug.pb.go b/rpc/debug/debug.pb.go
index 78459b85514..30f042c2af2 100644
--- a/rpc/debug/debug.pb.go
+++ b/rpc/debug/debug.pb.go
@@ -47,7 +47,7 @@ const _ = proto.ProtoPackageIsVersion4
 
 // The top-level message sent by the client for the `Debug` method.
 // Multiple `DebugReq` messages can be sent but the first message
-// must contain a `DebugReq` message to initialize the debug session.
+// must contain a `DebugConfigReq` message to initialize the debug session.
 // All subsequent messages must contain bytes to be sent to the debug session
 // and must not contain a `DebugReq` message.
 type DebugReq struct {
@@ -132,18 +132,16 @@ type DebugConfigReq struct {
 	// Path to the sketch that is running on the board. The compiled executable
 	// is expected to be located under this path.
 	SketchPath string `protobuf:"bytes,3,opt,name=sketch_path,json=sketchPath,proto3" json:"sketch_path,omitempty"`
-	// Port of the debugger. Set to `none` if the debugger doesn't use a port.
+	// Port of the debugger (optional).
 	Port string `protobuf:"bytes,4,opt,name=port,proto3" json:"port,omitempty"`
 	// Which GDB command interpreter to use.
 	Interpreter string `protobuf:"bytes,5,opt,name=interpreter,proto3" json:"interpreter,omitempty"`
-	// DEPRECATED: use import_dir instead
-	//
-	// Deprecated: Do not use.
-	ImportFile string `protobuf:"bytes,7,opt,name=import_file,json=importFile,proto3" json:"import_file,omitempty"`
 	// Directory containing the compiled executable. If `import_dir` is not
 	// specified, the executable is assumed to be in
 	// `{sketch_path}/build/{fqbn}/`.
 	ImportDir string `protobuf:"bytes,8,opt,name=import_dir,json=importDir,proto3" json:"import_dir,omitempty"`
+	// The programmer to use for debugging.
+	Programmer string `protobuf:"bytes,9,opt,name=programmer,proto3" json:"programmer,omitempty"`
 }
 
 func (x *DebugConfigReq) Reset() {
@@ -213,17 +211,16 @@ func (x *DebugConfigReq) GetInterpreter() string {
 	return ""
 }
 
-// Deprecated: Do not use.
-func (x *DebugConfigReq) GetImportFile() string {
+func (x *DebugConfigReq) GetImportDir() string {
 	if x != nil {
-		return x.ImportFile
+		return x.ImportDir
 	}
 	return ""
 }
 
-func (x *DebugConfigReq) GetImportDir() string {
+func (x *DebugConfigReq) GetProgrammer() string {
 	if x != nil {
-		return x.ImportDir
+		return x.Programmer
 	}
 	return ""
 }
@@ -286,6 +283,117 @@ func (x *DebugResp) GetError() string {
 	return ""
 }
 
+type GetDebugConfigResp struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	// The executable binary to debug
+	Executable string `protobuf:"bytes,1,opt,name=executable,proto3" json:"executable,omitempty"`
+	// The toolchain type used for the build (for example "gcc")
+	Toolchain string `protobuf:"bytes,2,opt,name=toolchain,proto3" json:"toolchain,omitempty"`
+	// The toolchain directory
+	ToolchainPath string `protobuf:"bytes,3,opt,name=toolchain_path,json=toolchainPath,proto3" json:"toolchain_path,omitempty"`
+	// The toolchain architecture prefix (for example "arm-none-eabi-")
+	ToolchainPrefix string `protobuf:"bytes,4,opt,name=toolchain_prefix,json=toolchainPrefix,proto3" json:"toolchain_prefix,omitempty"`
+	// The GDB server type used to connect to the programmer/board (for example "openocd")
+	Server string `protobuf:"bytes,5,opt,name=server,proto3" json:"server,omitempty"`
+	// The GDB server directory
+	ServerPath string `protobuf:"bytes,6,opt,name=server_path,json=serverPath,proto3" json:"server_path,omitempty"`
+	// Extra configuration parameters wrt toolchain
+	ToolchainConfiguration map[string]string `protobuf:"bytes,7,rep,name=toolchain_configuration,json=toolchainConfiguration,proto3" json:"toolchain_configuration,omitempty" protobuf_key:"bytes,1,opt,name=key,proto3" protobuf_val:"bytes,2,opt,name=value,proto3"`
+	// Extra configuration parameters wrt GDB server
+	ServerConfiguration map[string]string `protobuf:"bytes,8,rep,name=server_configuration,json=serverConfiguration,proto3" json:"server_configuration,omitempty" protobuf_key:"bytes,1,opt,name=key,proto3" protobuf_val:"bytes,2,opt,name=value,proto3"`
+}
+
+func (x *GetDebugConfigResp) Reset() {
+	*x = GetDebugConfigResp{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_debug_debug_proto_msgTypes[3]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *GetDebugConfigResp) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*GetDebugConfigResp) ProtoMessage() {}
+
+func (x *GetDebugConfigResp) ProtoReflect() protoreflect.Message {
+	mi := &file_debug_debug_proto_msgTypes[3]
+	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 GetDebugConfigResp.ProtoReflect.Descriptor instead.
+func (*GetDebugConfigResp) Descriptor() ([]byte, []int) {
+	return file_debug_debug_proto_rawDescGZIP(), []int{3}
+}
+
+func (x *GetDebugConfigResp) GetExecutable() string {
+	if x != nil {
+		return x.Executable
+	}
+	return ""
+}
+
+func (x *GetDebugConfigResp) GetToolchain() string {
+	if x != nil {
+		return x.Toolchain
+	}
+	return ""
+}
+
+func (x *GetDebugConfigResp) GetToolchainPath() string {
+	if x != nil {
+		return x.ToolchainPath
+	}
+	return ""
+}
+
+func (x *GetDebugConfigResp) GetToolchainPrefix() string {
+	if x != nil {
+		return x.ToolchainPrefix
+	}
+	return ""
+}
+
+func (x *GetDebugConfigResp) GetServer() string {
+	if x != nil {
+		return x.Server
+	}
+	return ""
+}
+
+func (x *GetDebugConfigResp) GetServerPath() string {
+	if x != nil {
+		return x.ServerPath
+	}
+	return ""
+}
+
+func (x *GetDebugConfigResp) GetToolchainConfiguration() map[string]string {
+	if x != nil {
+		return x.ToolchainConfiguration
+	}
+	return nil
+}
+
+func (x *GetDebugConfigResp) GetServerConfiguration() map[string]string {
+	if x != nil {
+		return x.ServerConfiguration
+	}
+	return nil
+}
+
 var File_debug_debug_proto protoreflect.FileDescriptor
 
 var file_debug_debug_proto_rawDesc = []byte{
@@ -301,7 +409,7 @@ var file_debug_debug_proto_rawDesc = []byte{
 	0x12, 0x0a, 0x04, 0x64, 0x61, 0x74, 0x61, 0x18, 0x02, 0x20, 0x01, 0x28, 0x0c, 0x52, 0x04, 0x64,
 	0x61, 0x74, 0x61, 0x12, 0x25, 0x0a, 0x0e, 0x73, 0x65, 0x6e, 0x64, 0x5f, 0x69, 0x6e, 0x74, 0x65,
 	0x72, 0x72, 0x75, 0x70, 0x74, 0x18, 0x03, 0x20, 0x01, 0x28, 0x08, 0x52, 0x0d, 0x73, 0x65, 0x6e,
-	0x64, 0x49, 0x6e, 0x74, 0x65, 0x72, 0x72, 0x75, 0x70, 0x74, 0x22, 0xfe, 0x01, 0x0a, 0x0e, 0x44,
+	0x64, 0x49, 0x6e, 0x74, 0x65, 0x72, 0x72, 0x75, 0x70, 0x74, 0x22, 0xf9, 0x01, 0x0a, 0x0e, 0x44,
 	0x65, 0x62, 0x75, 0x67, 0x43, 0x6f, 0x6e, 0x66, 0x69, 0x67, 0x52, 0x65, 0x71, 0x12, 0x3d, 0x0a,
 	0x08, 0x69, 0x6e, 0x73, 0x74, 0x61, 0x6e, 0x63, 0x65, 0x18, 0x01, 0x20, 0x01, 0x28, 0x0b, 0x32,
 	0x21, 0x2e, 0x63, 0x63, 0x2e, 0x61, 0x72, 0x64, 0x75, 0x69, 0x6e, 0x6f, 0x2e, 0x63, 0x6c, 0x69,
@@ -313,23 +421,68 @@ var file_debug_debug_proto_rawDesc = []byte{
 	0x68, 0x12, 0x12, 0x0a, 0x04, 0x70, 0x6f, 0x72, 0x74, 0x18, 0x04, 0x20, 0x01, 0x28, 0x09, 0x52,
 	0x04, 0x70, 0x6f, 0x72, 0x74, 0x12, 0x20, 0x0a, 0x0b, 0x69, 0x6e, 0x74, 0x65, 0x72, 0x70, 0x72,
 	0x65, 0x74, 0x65, 0x72, 0x18, 0x05, 0x20, 0x01, 0x28, 0x09, 0x52, 0x0b, 0x69, 0x6e, 0x74, 0x65,
-	0x72, 0x70, 0x72, 0x65, 0x74, 0x65, 0x72, 0x12, 0x23, 0x0a, 0x0b, 0x69, 0x6d, 0x70, 0x6f, 0x72,
-	0x74, 0x5f, 0x66, 0x69, 0x6c, 0x65, 0x18, 0x07, 0x20, 0x01, 0x28, 0x09, 0x42, 0x02, 0x18, 0x01,
-	0x52, 0x0a, 0x69, 0x6d, 0x70, 0x6f, 0x72, 0x74, 0x46, 0x69, 0x6c, 0x65, 0x12, 0x1d, 0x0a, 0x0a,
-	0x69, 0x6d, 0x70, 0x6f, 0x72, 0x74, 0x5f, 0x64, 0x69, 0x72, 0x18, 0x08, 0x20, 0x01, 0x28, 0x09,
-	0x52, 0x09, 0x69, 0x6d, 0x70, 0x6f, 0x72, 0x74, 0x44, 0x69, 0x72, 0x22, 0x35, 0x0a, 0x09, 0x44,
-	0x65, 0x62, 0x75, 0x67, 0x52, 0x65, 0x73, 0x70, 0x12, 0x12, 0x0a, 0x04, 0x64, 0x61, 0x74, 0x61,
-	0x18, 0x01, 0x20, 0x01, 0x28, 0x0c, 0x52, 0x04, 0x64, 0x61, 0x74, 0x61, 0x12, 0x14, 0x0a, 0x05,
-	0x65, 0x72, 0x72, 0x6f, 0x72, 0x18, 0x02, 0x20, 0x01, 0x28, 0x09, 0x52, 0x05, 0x65, 0x72, 0x72,
-	0x6f, 0x72, 0x32, 0x57, 0x0a, 0x05, 0x44, 0x65, 0x62, 0x75, 0x67, 0x12, 0x4e, 0x0a, 0x05, 0x44,
-	0x65, 0x62, 0x75, 0x67, 0x12, 0x1e, 0x2e, 0x63, 0x63, 0x2e, 0x61, 0x72, 0x64, 0x75, 0x69, 0x6e,
-	0x6f, 0x2e, 0x63, 0x6c, 0x69, 0x2e, 0x64, 0x65, 0x62, 0x75, 0x67, 0x2e, 0x44, 0x65, 0x62, 0x75,
-	0x67, 0x52, 0x65, 0x71, 0x1a, 0x1f, 0x2e, 0x63, 0x63, 0x2e, 0x61, 0x72, 0x64, 0x75, 0x69, 0x6e,
-	0x6f, 0x2e, 0x63, 0x6c, 0x69, 0x2e, 0x64, 0x65, 0x62, 0x75, 0x67, 0x2e, 0x44, 0x65, 0x62, 0x75,
-	0x67, 0x52, 0x65, 0x73, 0x70, 0x22, 0x00, 0x28, 0x01, 0x30, 0x01, 0x42, 0x2a, 0x5a, 0x28, 0x67,
-	0x69, 0x74, 0x68, 0x75, 0x62, 0x2e, 0x63, 0x6f, 0x6d, 0x2f, 0x61, 0x72, 0x64, 0x75, 0x69, 0x6e,
-	0x6f, 0x2f, 0x61, 0x72, 0x64, 0x75, 0x69, 0x6e, 0x6f, 0x2d, 0x63, 0x6c, 0x69, 0x2f, 0x72, 0x70,
-	0x63, 0x2f, 0x64, 0x65, 0x62, 0x75, 0x67, 0x62, 0x06, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x33,
+	0x72, 0x70, 0x72, 0x65, 0x74, 0x65, 0x72, 0x12, 0x1d, 0x0a, 0x0a, 0x69, 0x6d, 0x70, 0x6f, 0x72,
+	0x74, 0x5f, 0x64, 0x69, 0x72, 0x18, 0x08, 0x20, 0x01, 0x28, 0x09, 0x52, 0x09, 0x69, 0x6d, 0x70,
+	0x6f, 0x72, 0x74, 0x44, 0x69, 0x72, 0x12, 0x1e, 0x0a, 0x0a, 0x70, 0x72, 0x6f, 0x67, 0x72, 0x61,
+	0x6d, 0x6d, 0x65, 0x72, 0x18, 0x09, 0x20, 0x01, 0x28, 0x09, 0x52, 0x0a, 0x70, 0x72, 0x6f, 0x67,
+	0x72, 0x61, 0x6d, 0x6d, 0x65, 0x72, 0x22, 0x35, 0x0a, 0x09, 0x44, 0x65, 0x62, 0x75, 0x67, 0x52,
+	0x65, 0x73, 0x70, 0x12, 0x12, 0x0a, 0x04, 0x64, 0x61, 0x74, 0x61, 0x18, 0x01, 0x20, 0x01, 0x28,
+	0x0c, 0x52, 0x04, 0x64, 0x61, 0x74, 0x61, 0x12, 0x14, 0x0a, 0x05, 0x65, 0x72, 0x72, 0x6f, 0x72,
+	0x18, 0x02, 0x20, 0x01, 0x28, 0x09, 0x52, 0x05, 0x65, 0x72, 0x72, 0x6f, 0x72, 0x22, 0xe5, 0x04,
+	0x0a, 0x12, 0x47, 0x65, 0x74, 0x44, 0x65, 0x62, 0x75, 0x67, 0x43, 0x6f, 0x6e, 0x66, 0x69, 0x67,
+	0x52, 0x65, 0x73, 0x70, 0x12, 0x1e, 0x0a, 0x0a, 0x65, 0x78, 0x65, 0x63, 0x75, 0x74, 0x61, 0x62,
+	0x6c, 0x65, 0x18, 0x01, 0x20, 0x01, 0x28, 0x09, 0x52, 0x0a, 0x65, 0x78, 0x65, 0x63, 0x75, 0x74,
+	0x61, 0x62, 0x6c, 0x65, 0x12, 0x1c, 0x0a, 0x09, 0x74, 0x6f, 0x6f, 0x6c, 0x63, 0x68, 0x61, 0x69,
+	0x6e, 0x18, 0x02, 0x20, 0x01, 0x28, 0x09, 0x52, 0x09, 0x74, 0x6f, 0x6f, 0x6c, 0x63, 0x68, 0x61,
+	0x69, 0x6e, 0x12, 0x25, 0x0a, 0x0e, 0x74, 0x6f, 0x6f, 0x6c, 0x63, 0x68, 0x61, 0x69, 0x6e, 0x5f,
+	0x70, 0x61, 0x74, 0x68, 0x18, 0x03, 0x20, 0x01, 0x28, 0x09, 0x52, 0x0d, 0x74, 0x6f, 0x6f, 0x6c,
+	0x63, 0x68, 0x61, 0x69, 0x6e, 0x50, 0x61, 0x74, 0x68, 0x12, 0x29, 0x0a, 0x10, 0x74, 0x6f, 0x6f,
+	0x6c, 0x63, 0x68, 0x61, 0x69, 0x6e, 0x5f, 0x70, 0x72, 0x65, 0x66, 0x69, 0x78, 0x18, 0x04, 0x20,
+	0x01, 0x28, 0x09, 0x52, 0x0f, 0x74, 0x6f, 0x6f, 0x6c, 0x63, 0x68, 0x61, 0x69, 0x6e, 0x50, 0x72,
+	0x65, 0x66, 0x69, 0x78, 0x12, 0x16, 0x0a, 0x06, 0x73, 0x65, 0x72, 0x76, 0x65, 0x72, 0x18, 0x05,
+	0x20, 0x01, 0x28, 0x09, 0x52, 0x06, 0x73, 0x65, 0x72, 0x76, 0x65, 0x72, 0x12, 0x1f, 0x0a, 0x0b,
+	0x73, 0x65, 0x72, 0x76, 0x65, 0x72, 0x5f, 0x70, 0x61, 0x74, 0x68, 0x18, 0x06, 0x20, 0x01, 0x28,
+	0x09, 0x52, 0x0a, 0x73, 0x65, 0x72, 0x76, 0x65, 0x72, 0x50, 0x61, 0x74, 0x68, 0x12, 0x7d, 0x0a,
+	0x17, 0x74, 0x6f, 0x6f, 0x6c, 0x63, 0x68, 0x61, 0x69, 0x6e, 0x5f, 0x63, 0x6f, 0x6e, 0x66, 0x69,
+	0x67, 0x75, 0x72, 0x61, 0x74, 0x69, 0x6f, 0x6e, 0x18, 0x07, 0x20, 0x03, 0x28, 0x0b, 0x32, 0x44,
+	0x2e, 0x63, 0x63, 0x2e, 0x61, 0x72, 0x64, 0x75, 0x69, 0x6e, 0x6f, 0x2e, 0x63, 0x6c, 0x69, 0x2e,
+	0x64, 0x65, 0x62, 0x75, 0x67, 0x2e, 0x47, 0x65, 0x74, 0x44, 0x65, 0x62, 0x75, 0x67, 0x43, 0x6f,
+	0x6e, 0x66, 0x69, 0x67, 0x52, 0x65, 0x73, 0x70, 0x2e, 0x54, 0x6f, 0x6f, 0x6c, 0x63, 0x68, 0x61,
+	0x69, 0x6e, 0x43, 0x6f, 0x6e, 0x66, 0x69, 0x67, 0x75, 0x72, 0x61, 0x74, 0x69, 0x6f, 0x6e, 0x45,
+	0x6e, 0x74, 0x72, 0x79, 0x52, 0x16, 0x74, 0x6f, 0x6f, 0x6c, 0x63, 0x68, 0x61, 0x69, 0x6e, 0x43,
+	0x6f, 0x6e, 0x66, 0x69, 0x67, 0x75, 0x72, 0x61, 0x74, 0x69, 0x6f, 0x6e, 0x12, 0x74, 0x0a, 0x14,
+	0x73, 0x65, 0x72, 0x76, 0x65, 0x72, 0x5f, 0x63, 0x6f, 0x6e, 0x66, 0x69, 0x67, 0x75, 0x72, 0x61,
+	0x74, 0x69, 0x6f, 0x6e, 0x18, 0x08, 0x20, 0x03, 0x28, 0x0b, 0x32, 0x41, 0x2e, 0x63, 0x63, 0x2e,
+	0x61, 0x72, 0x64, 0x75, 0x69, 0x6e, 0x6f, 0x2e, 0x63, 0x6c, 0x69, 0x2e, 0x64, 0x65, 0x62, 0x75,
+	0x67, 0x2e, 0x47, 0x65, 0x74, 0x44, 0x65, 0x62, 0x75, 0x67, 0x43, 0x6f, 0x6e, 0x66, 0x69, 0x67,
+	0x52, 0x65, 0x73, 0x70, 0x2e, 0x53, 0x65, 0x72, 0x76, 0x65, 0x72, 0x43, 0x6f, 0x6e, 0x66, 0x69,
+	0x67, 0x75, 0x72, 0x61, 0x74, 0x69, 0x6f, 0x6e, 0x45, 0x6e, 0x74, 0x72, 0x79, 0x52, 0x13, 0x73,
+	0x65, 0x72, 0x76, 0x65, 0x72, 0x43, 0x6f, 0x6e, 0x66, 0x69, 0x67, 0x75, 0x72, 0x61, 0x74, 0x69,
+	0x6f, 0x6e, 0x1a, 0x49, 0x0a, 0x1b, 0x54, 0x6f, 0x6f, 0x6c, 0x63, 0x68, 0x61, 0x69, 0x6e, 0x43,
+	0x6f, 0x6e, 0x66, 0x69, 0x67, 0x75, 0x72, 0x61, 0x74, 0x69, 0x6f, 0x6e, 0x45, 0x6e, 0x74, 0x72,
+	0x79, 0x12, 0x10, 0x0a, 0x03, 0x6b, 0x65, 0x79, 0x18, 0x01, 0x20, 0x01, 0x28, 0x09, 0x52, 0x03,
+	0x6b, 0x65, 0x79, 0x12, 0x14, 0x0a, 0x05, 0x76, 0x61, 0x6c, 0x75, 0x65, 0x18, 0x02, 0x20, 0x01,
+	0x28, 0x09, 0x52, 0x05, 0x76, 0x61, 0x6c, 0x75, 0x65, 0x3a, 0x02, 0x38, 0x01, 0x1a, 0x46, 0x0a,
+	0x18, 0x53, 0x65, 0x72, 0x76, 0x65, 0x72, 0x43, 0x6f, 0x6e, 0x66, 0x69, 0x67, 0x75, 0x72, 0x61,
+	0x74, 0x69, 0x6f, 0x6e, 0x45, 0x6e, 0x74, 0x72, 0x79, 0x12, 0x10, 0x0a, 0x03, 0x6b, 0x65, 0x79,
+	0x18, 0x01, 0x20, 0x01, 0x28, 0x09, 0x52, 0x03, 0x6b, 0x65, 0x79, 0x12, 0x14, 0x0a, 0x05, 0x76,
+	0x61, 0x6c, 0x75, 0x65, 0x18, 0x02, 0x20, 0x01, 0x28, 0x09, 0x52, 0x05, 0x76, 0x61, 0x6c, 0x75,
+	0x65, 0x3a, 0x02, 0x38, 0x01, 0x32, 0xbb, 0x01, 0x0a, 0x05, 0x44, 0x65, 0x62, 0x75, 0x67, 0x12,
+	0x4e, 0x0a, 0x05, 0x44, 0x65, 0x62, 0x75, 0x67, 0x12, 0x1e, 0x2e, 0x63, 0x63, 0x2e, 0x61, 0x72,
+	0x64, 0x75, 0x69, 0x6e, 0x6f, 0x2e, 0x63, 0x6c, 0x69, 0x2e, 0x64, 0x65, 0x62, 0x75, 0x67, 0x2e,
+	0x44, 0x65, 0x62, 0x75, 0x67, 0x52, 0x65, 0x71, 0x1a, 0x1f, 0x2e, 0x63, 0x63, 0x2e, 0x61, 0x72,
+	0x64, 0x75, 0x69, 0x6e, 0x6f, 0x2e, 0x63, 0x6c, 0x69, 0x2e, 0x64, 0x65, 0x62, 0x75, 0x67, 0x2e,
+	0x44, 0x65, 0x62, 0x75, 0x67, 0x52, 0x65, 0x73, 0x70, 0x22, 0x00, 0x28, 0x01, 0x30, 0x01, 0x12,
+	0x62, 0x0a, 0x0e, 0x47, 0x65, 0x74, 0x44, 0x65, 0x62, 0x75, 0x67, 0x43, 0x6f, 0x6e, 0x66, 0x69,
+	0x67, 0x12, 0x24, 0x2e, 0x63, 0x63, 0x2e, 0x61, 0x72, 0x64, 0x75, 0x69, 0x6e, 0x6f, 0x2e, 0x63,
+	0x6c, 0x69, 0x2e, 0x64, 0x65, 0x62, 0x75, 0x67, 0x2e, 0x44, 0x65, 0x62, 0x75, 0x67, 0x43, 0x6f,
+	0x6e, 0x66, 0x69, 0x67, 0x52, 0x65, 0x71, 0x1a, 0x28, 0x2e, 0x63, 0x63, 0x2e, 0x61, 0x72, 0x64,
+	0x75, 0x69, 0x6e, 0x6f, 0x2e, 0x63, 0x6c, 0x69, 0x2e, 0x64, 0x65, 0x62, 0x75, 0x67, 0x2e, 0x47,
+	0x65, 0x74, 0x44, 0x65, 0x62, 0x75, 0x67, 0x43, 0x6f, 0x6e, 0x66, 0x69, 0x67, 0x52, 0x65, 0x73,
+	0x70, 0x22, 0x00, 0x42, 0x2a, 0x5a, 0x28, 0x67, 0x69, 0x74, 0x68, 0x75, 0x62, 0x2e, 0x63, 0x6f,
+	0x6d, 0x2f, 0x61, 0x72, 0x64, 0x75, 0x69, 0x6e, 0x6f, 0x2f, 0x61, 0x72, 0x64, 0x75, 0x69, 0x6e,
+	0x6f, 0x2d, 0x63, 0x6c, 0x69, 0x2f, 0x72, 0x70, 0x63, 0x2f, 0x64, 0x65, 0x62, 0x75, 0x67, 0x62,
+	0x06, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x33,
 }
 
 var (
@@ -344,23 +497,30 @@ func file_debug_debug_proto_rawDescGZIP() []byte {
 	return file_debug_debug_proto_rawDescData
 }
 
-var file_debug_debug_proto_msgTypes = make([]protoimpl.MessageInfo, 3)
+var file_debug_debug_proto_msgTypes = make([]protoimpl.MessageInfo, 6)
 var file_debug_debug_proto_goTypes = []interface{}{
-	(*DebugReq)(nil),          // 0: cc.arduino.cli.debug.DebugReq
-	(*DebugConfigReq)(nil),    // 1: cc.arduino.cli.debug.DebugConfigReq
-	(*DebugResp)(nil),         // 2: cc.arduino.cli.debug.DebugResp
-	(*commands.Instance)(nil), // 3: cc.arduino.cli.commands.Instance
+	(*DebugReq)(nil),           // 0: cc.arduino.cli.debug.DebugReq
+	(*DebugConfigReq)(nil),     // 1: cc.arduino.cli.debug.DebugConfigReq
+	(*DebugResp)(nil),          // 2: cc.arduino.cli.debug.DebugResp
+	(*GetDebugConfigResp)(nil), // 3: cc.arduino.cli.debug.GetDebugConfigResp
+	nil,                        // 4: cc.arduino.cli.debug.GetDebugConfigResp.ToolchainConfigurationEntry
+	nil,                        // 5: cc.arduino.cli.debug.GetDebugConfigResp.ServerConfigurationEntry
+	(*commands.Instance)(nil),  // 6: cc.arduino.cli.commands.Instance
 }
 var file_debug_debug_proto_depIdxs = []int32{
 	1, // 0: cc.arduino.cli.debug.DebugReq.debugReq:type_name -> cc.arduino.cli.debug.DebugConfigReq
-	3, // 1: cc.arduino.cli.debug.DebugConfigReq.instance:type_name -> cc.arduino.cli.commands.Instance
-	0, // 2: cc.arduino.cli.debug.Debug.Debug:input_type -> cc.arduino.cli.debug.DebugReq
-	2, // 3: cc.arduino.cli.debug.Debug.Debug:output_type -> cc.arduino.cli.debug.DebugResp
-	3, // [3:4] is the sub-list for method output_type
-	2, // [2:3] is the sub-list for method input_type
-	2, // [2:2] is the sub-list for extension type_name
-	2, // [2:2] is the sub-list for extension extendee
-	0, // [0:2] is the sub-list for field type_name
+	6, // 1: cc.arduino.cli.debug.DebugConfigReq.instance:type_name -> cc.arduino.cli.commands.Instance
+	4, // 2: cc.arduino.cli.debug.GetDebugConfigResp.toolchain_configuration:type_name -> cc.arduino.cli.debug.GetDebugConfigResp.ToolchainConfigurationEntry
+	5, // 3: cc.arduino.cli.debug.GetDebugConfigResp.server_configuration:type_name -> cc.arduino.cli.debug.GetDebugConfigResp.ServerConfigurationEntry
+	0, // 4: cc.arduino.cli.debug.Debug.Debug:input_type -> cc.arduino.cli.debug.DebugReq
+	1, // 5: cc.arduino.cli.debug.Debug.GetDebugConfig:input_type -> cc.arduino.cli.debug.DebugConfigReq
+	2, // 6: cc.arduino.cli.debug.Debug.Debug:output_type -> cc.arduino.cli.debug.DebugResp
+	3, // 7: cc.arduino.cli.debug.Debug.GetDebugConfig:output_type -> cc.arduino.cli.debug.GetDebugConfigResp
+	6, // [6:8] is the sub-list for method output_type
+	4, // [4:6] is the sub-list for method input_type
+	4, // [4:4] is the sub-list for extension type_name
+	4, // [4:4] is the sub-list for extension extendee
+	0, // [0:4] is the sub-list for field type_name
 }
 
 func init() { file_debug_debug_proto_init() }
@@ -405,6 +565,18 @@ func file_debug_debug_proto_init() {
 				return nil
 			}
 		}
+		file_debug_debug_proto_msgTypes[3].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*GetDebugConfigResp); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
 	}
 	type x struct{}
 	out := protoimpl.TypeBuilder{
@@ -412,7 +584,7 @@ func file_debug_debug_proto_init() {
 			GoPackagePath: reflect.TypeOf(x{}).PkgPath(),
 			RawDescriptor: file_debug_debug_proto_rawDesc,
 			NumEnums:      0,
-			NumMessages:   3,
+			NumMessages:   6,
 			NumExtensions: 0,
 			NumServices:   1,
 		},
@@ -440,6 +612,7 @@ const _ = grpc.SupportPackageIsVersion6
 type DebugClient interface {
 	// Start a debug session and communicate with the debugger tool.
 	Debug(ctx context.Context, opts ...grpc.CallOption) (Debug_DebugClient, error)
+	GetDebugConfig(ctx context.Context, in *DebugConfigReq, opts ...grpc.CallOption) (*GetDebugConfigResp, error)
 }
 
 type debugClient struct {
@@ -481,10 +654,20 @@ func (x *debugDebugClient) Recv() (*DebugResp, error) {
 	return m, nil
 }
 
+func (c *debugClient) GetDebugConfig(ctx context.Context, in *DebugConfigReq, opts ...grpc.CallOption) (*GetDebugConfigResp, error) {
+	out := new(GetDebugConfigResp)
+	err := c.cc.Invoke(ctx, "/cc.arduino.cli.debug.Debug/GetDebugConfig", in, out, opts...)
+	if err != nil {
+		return nil, err
+	}
+	return out, nil
+}
+
 // DebugServer is the server API for Debug service.
 type DebugServer interface {
 	// Start a debug session and communicate with the debugger tool.
 	Debug(Debug_DebugServer) error
+	GetDebugConfig(context.Context, *DebugConfigReq) (*GetDebugConfigResp, error)
 }
 
 // UnimplementedDebugServer can be embedded to have forward compatible implementations.
@@ -494,6 +677,9 @@ type UnimplementedDebugServer struct {
 func (*UnimplementedDebugServer) Debug(Debug_DebugServer) error {
 	return status.Errorf(codes.Unimplemented, "method Debug not implemented")
 }
+func (*UnimplementedDebugServer) GetDebugConfig(context.Context, *DebugConfigReq) (*GetDebugConfigResp, error) {
+	return nil, status.Errorf(codes.Unimplemented, "method GetDebugConfig not implemented")
+}
 
 func RegisterDebugServer(s *grpc.Server, srv DebugServer) {
 	s.RegisterService(&_Debug_serviceDesc, srv)
@@ -525,10 +711,33 @@ func (x *debugDebugServer) Recv() (*DebugReq, error) {
 	return m, nil
 }
 
+func _Debug_GetDebugConfig_Handler(srv interface{}, ctx context.Context, dec func(interface{}) error, interceptor grpc.UnaryServerInterceptor) (interface{}, error) {
+	in := new(DebugConfigReq)
+	if err := dec(in); err != nil {
+		return nil, err
+	}
+	if interceptor == nil {
+		return srv.(DebugServer).GetDebugConfig(ctx, in)
+	}
+	info := &grpc.UnaryServerInfo{
+		Server:     srv,
+		FullMethod: "/cc.arduino.cli.debug.Debug/GetDebugConfig",
+	}
+	handler := func(ctx context.Context, req interface{}) (interface{}, error) {
+		return srv.(DebugServer).GetDebugConfig(ctx, req.(*DebugConfigReq))
+	}
+	return interceptor(ctx, in, info, handler)
+}
+
 var _Debug_serviceDesc = grpc.ServiceDesc{
 	ServiceName: "cc.arduino.cli.debug.Debug",
 	HandlerType: (*DebugServer)(nil),
-	Methods:     []grpc.MethodDesc{},
+	Methods: []grpc.MethodDesc{
+		{
+			MethodName: "GetDebugConfig",
+			Handler:    _Debug_GetDebugConfig_Handler,
+		},
+	},
 	Streams: []grpc.StreamDesc{
 		{
 			StreamName:    "Debug",
diff --git a/rpc/debug/debug.proto b/rpc/debug/debug.proto
index 8d478089176..087022173a3 100644
--- a/rpc/debug/debug.proto
+++ b/rpc/debug/debug.proto
@@ -26,11 +26,13 @@ service Debug {
     // Start a debug session and communicate with the debugger tool.
     rpc Debug (stream DebugReq) returns (stream DebugResp) {
     }
+
+    rpc GetDebugConfig(DebugConfigReq) returns (GetDebugConfigResp) {}
 }
 
 // The top-level message sent by the client for the `Debug` method.
 // Multiple `DebugReq` messages can be sent but the first message
-// must contain a `DebugReq` message to initialize the debug session.
+// must contain a `DebugConfigReq` message to initialize the debug session.
 // All subsequent messages must contain bytes to be sent to the debug session
 // and must not contain a `DebugReq` message.
 message DebugReq {
@@ -58,16 +60,16 @@ message DebugConfigReq {
     // Path to the sketch that is running on the board. The compiled executable
     // is expected to be located under this path.
     string sketch_path = 3;
-    // Port of the debugger. Set to `none` if the debugger doesn't use a port.
+    // Port of the debugger (optional).
     string port = 4;
     // Which GDB command interpreter to use.
     string interpreter = 5;
-    // DEPRECATED: use import_dir instead
-    string import_file = 7 [deprecated = true];
     // Directory containing the compiled executable. If `import_dir` is not
     // specified, the executable is assumed to be in
     // `{sketch_path}/build/{fqbn}/`.
     string import_dir = 8;
+    // The programmer to use for debugging.
+    string programmer = 9;
 }
 
 //
@@ -77,3 +79,22 @@ message DebugResp {
     // Incoming error output from the debugger tool.
     string error = 2;
 }
+
+message GetDebugConfigResp {
+    // The executable binary to debug
+    string executable = 1;
+    // The toolchain type used for the build (for example "gcc")
+    string toolchain = 2;
+    // The toolchain directory
+    string toolchain_path = 3;
+    // The toolchain architecture prefix (for example "arm-none-eabi-")
+    string toolchain_prefix = 4;
+    // The GDB server type used to connect to the programmer/board (for example "openocd")
+    string server = 5;
+    // The GDB server directory
+    string server_path = 6;
+    // Extra configuration parameters wrt toolchain
+    map<string, string> toolchain_configuration = 7;
+    // Extra configuration parameters wrt GDB server
+    map<string, string> server_configuration = 8;
+}