diff --git a/Documentation/usage/dlv_debug.md b/Documentation/usage/dlv_debug.md
index 718ae476..23c75ea8 100644
--- a/Documentation/usage/dlv_debug.md
+++ b/Documentation/usage/dlv_debug.md
@@ -20,7 +20,7 @@ dlv debug [package] [flags]
 ```
       --continue        Continue the debugged process on start.
   -h, --help            help for debug
-      --output string   Output path for the binary. (default "./__debug_bin")
+      --output string   Output path for the binary.
       --tty string      TTY to use for the target program
 ```
 
diff --git a/Documentation/usage/dlv_test.md b/Documentation/usage/dlv_test.md
index d7817541..37a9fe0f 100644
--- a/Documentation/usage/dlv_test.md
+++ b/Documentation/usage/dlv_test.md
@@ -23,7 +23,7 @@ dlv test [package] [flags]
 
 ```
   -h, --help            help for test
-      --output string   Output path for the binary. (default "debug.test")
+      --output string   Output path for the binary.
 ```
 
 ### Options inherited from parent commands
diff --git a/Documentation/usage/dlv_trace.md b/Documentation/usage/dlv_trace.md
index 018a5114..a6428100 100644
--- a/Documentation/usage/dlv_trace.md
+++ b/Documentation/usage/dlv_trace.md
@@ -24,7 +24,7 @@ dlv trace [package] regexp [flags]
       --ebpf            Trace using eBPF (experimental).
   -e, --exec string     Binary file to exec and trace.
   -h, --help            help for trace
-      --output string   Output path for the binary. (default "debug")
+      --output string   Output path for the binary.
   -p, --pid int         Pid to attach to.
   -s, --stack int       Show stack trace with given depth. (Ignored with --ebpf)
   -t, --test            Trace a test binary.
diff --git a/cmd/dlv/cmds/commands.go b/cmd/dlv/cmds/commands.go
index 44ab2ae2..a189e480 100644
--- a/cmd/dlv/cmds/commands.go
+++ b/cmd/dlv/cmds/commands.go
@@ -230,7 +230,7 @@ package name and Delve will compile that package instead, and begin a new debug
 session.`,
 		Run: debugCmd,
 	}
-	debugCommand.Flags().String("output", "./__debug_bin", "Output path for the binary.")
+	debugCommand.Flags().String("output", "", "Output path for the binary.")
 	debugCommand.Flags().BoolVar(&continueOnStart, "continue", false, "Continue the debugged process on start.")
 	debugCommand.Flags().StringVar(&tty, "tty", "", "TTY to use for the target program")
 	rootCommand.AddCommand(debugCommand)
@@ -287,7 +287,7 @@ dlv test [package] -- -test.run TestSomething -test.v -other-argument
 See also: 'go help testflag'.`,
 		Run: testCmd,
 	}
-	testCommand.Flags().String("output", "debug.test", "Output path for the binary.")
+	testCommand.Flags().String("output", "", "Output path for the binary.")
 	rootCommand.AddCommand(testCommand)
 
 	// 'trace' subcommand.
@@ -311,7 +311,7 @@ only see the output of the trace operations you can redirect stdout.`,
 	traceCommand.Flags().BoolVarP(&traceUseEBPF, "ebpf", "", false, "Trace using eBPF (experimental).")
 	traceCommand.Flags().BoolVarP(&traceShowTimestamp, "timestamp", "", false, "Show timestamp in the output")
 	traceCommand.Flags().IntVarP(&traceStackDepth, "stack", "s", 0, "Show stack trace with given depth. (Ignored with --ebpf)")
-	traceCommand.Flags().String("output", "debug", "Output path for the binary.")
+	traceCommand.Flags().String("output", "", "Output path for the binary.")
 	rootCommand.AddCommand(traceCommand)
 
 	coreCommand := &cobra.Command{
@@ -528,10 +528,21 @@ func dapCmd(cmd *cobra.Command, args []string) {
 }
 
 func buildBinary(cmd *cobra.Command, args []string, isTest bool) (string, bool) {
-	debugname, err := filepath.Abs(cmd.Flag("output").Value.String())
-	if err != nil {
-		fmt.Fprintf(os.Stderr, "%v\n", err)
-		return "", false
+	outputFlag := cmd.Flag("output").Value.String()
+	var debugname string
+	var err error
+	if outputFlag == "" {
+		if isTest {
+			debugname = gobuild.DefaultDebugBinaryPath("debug.test")
+		} else {
+			debugname = gobuild.DefaultDebugBinaryPath("__debug_bin")
+		}
+	} else {
+		debugname, err = filepath.Abs(outputFlag)
+		if err != nil {
+			fmt.Fprintf(os.Stderr, "%v\n", err)
+			return "", false
+		}
 	}
 
 	if isTest {
@@ -540,6 +551,9 @@ func buildBinary(cmd *cobra.Command, args []string, isTest bool) (string, bool)
 		err = gobuild.GoBuild(debugname, args, buildFlags)
 	}
 	if err != nil {
+		if outputFlag == "" {
+			gobuild.Remove(debugname)
+		}
 		fmt.Fprintf(os.Stderr, "%v\n", err)
 		return "", false
 	}
diff --git a/cmd/dlv/dlv_test.go b/cmd/dlv/dlv_test.go
index e1c30065..06b8fd60 100644
--- a/cmd/dlv/dlv_test.go
+++ b/cmd/dlv/dlv_test.go
@@ -239,7 +239,7 @@ func getDlvBinInternal(t *testing.T, goflags ...string) string {
 func TestOutput(t *testing.T) {
 	dlvbin := getDlvBin(t)
 
-	for _, output := range []string{"", "myownname", filepath.Join(t.TempDir(), "absolute.path")} {
+	for _, output := range []string{"__debug_bin", "myownname", filepath.Join(t.TempDir(), "absolute.path")} {
 		testOutput(t, dlvbin, output, []string{"exit"})
 
 		const hello = "hello world!"
@@ -1327,3 +1327,39 @@ func TestStaticcheck(t *testing.T) {
 	out, _ := cmd.CombinedOutput()
 	checkAutogenDoc(t, "_scripts/staticcheck-out.txt", fmt.Sprintf("staticcheck %s > _scripts/staticcheck-out.txt", strings.Join(args, " ")), out)
 }
+
+func TestDefaultBinary(t *testing.T) {
+	// Check that when delve is run twice in the same directory simultaneously
+	// it will pick different default output binary paths.
+	dlvbin := getDlvBin(t)
+	fixture := filepath.Join(protest.FindFixturesDir(), "testargs.go")
+
+	startOne := func() (io.WriteCloser, func() error, *bytes.Buffer) {
+		cmd := exec.Command(dlvbin, "debug", "--allow-non-terminal-interactive=true", fixture, "--", "test")
+		stdin, _ := cmd.StdinPipe()
+		stdoutBuf := new(bytes.Buffer)
+		cmd.Stdout = stdoutBuf
+
+		assertNoError(cmd.Start(), t, "dlv debug")
+		return stdin, cmd.Wait, stdoutBuf
+	}
+
+	stdin1, wait1, stdoutBuf1 := startOne()
+	defer stdin1.Close()
+
+	stdin2, wait2, stdoutBuf2 := startOne()
+	defer stdin2.Close()
+
+	fmt.Fprintf(stdin1, "continue\nquit\n")
+	fmt.Fprintf(stdin2, "continue\nquit\n")
+
+	wait1()
+	wait2()
+
+	out1, out2 := stdoutBuf1.String(), stdoutBuf2.String()
+	t.Logf("%q", out1)
+	t.Logf("%q", out2)
+	if out1 == out2 {
+		t.Errorf("outputs match")
+	}
+}
diff --git a/pkg/gobuild/defaultexe.go b/pkg/gobuild/defaultexe.go
new file mode 100644
index 00000000..14fb313f
--- /dev/null
+++ b/pkg/gobuild/defaultexe.go
@@ -0,0 +1,28 @@
+package gobuild
+
+import (
+	"io/ioutil"
+	"runtime"
+
+	"github.com/go-delve/delve/pkg/logflags"
+)
+
+// DefaultDebugBinaryPath returns an unused file path in the current
+// directory named 'name' followed by a random string
+func DefaultDebugBinaryPath(name string) string {
+	pattern := name
+	if runtime.GOOS == "windows" {
+		pattern += "*.exe"
+	}
+	f, err := ioutil.TempFile(".", pattern)
+	if err != nil {
+		logflags.DebuggerLogger().Errorf("could not create temporary file for build output: %v", err)
+		if runtime.GOOS == "windows" {
+			return name + ".exe"
+		}
+		return name
+	}
+	r := f.Name()
+	f.Close()
+	return r
+}
diff --git a/service/dap/server.go b/service/dap/server.go
index ecebb778..2b0532e2 100644
--- a/service/dap/server.go
+++ b/service/dap/server.go
@@ -859,10 +859,6 @@ func (s *Session) setClientCapabilities(args dap.InitializeRequestArguments) {
 	s.clientCapabilities.supportsVariableType = args.SupportsVariableType
 }
 
-// Default output file pathname for the compiled binary in debug or test modes.
-// This is relative to the current working directory of the server.
-const defaultDebugBinary string = "./__debug_bin"
-
 func cleanExeName(name string) string {
 	if runtime.GOOS == "windows" && filepath.Ext(name) != ".exe" {
 		return name + ".exe"
@@ -957,8 +953,10 @@ func (s *Session) onLaunchRequest(request *dap.LaunchRequest) {
 	// Prepare the debug executable filename, building it if necessary
 	debugbinary := args.Program
 	if args.Mode == "debug" || args.Mode == "test" {
+		deleteOnError := false
 		if args.Output == "" {
-			args.Output = cleanExeName(defaultDebugBinary)
+			deleteOnError = true
+			args.Output = gobuild.DefaultDebugBinaryPath("__debug_bin")
 		} else {
 			args.Output = cleanExeName(args.Output)
 		}
@@ -981,6 +979,9 @@ func (s *Session) onLaunchRequest(request *dap.LaunchRequest) {
 		args.DlvCwd, _ = filepath.Abs(args.DlvCwd)
 		s.config.log.Debugf("building from %q: [%s]", args.DlvCwd, cmd)
 		if err != nil {
+			if deleteOnError {
+				gobuild.Remove(args.Output)
+			}
 			s.send(&dap.OutputEvent{
 				Event: *newEvent("output"),
 				Body: dap.OutputEventBody{
@@ -1049,6 +1050,9 @@ func (s *Session) onLaunchRequest(request *dap.LaunchRequest) {
 		s.debugger, err = debugger.New(&s.config.Debugger, s.config.ProcessArgs)
 	}()
 	if err != nil {
+		if s.binaryToRemove != "" {
+			gobuild.Remove(s.binaryToRemove)
+		}
 		s.sendShowUserErrorResponse(request.Request, FailedToLaunch, "Failed to launch", err.Error())
 		return
 	}