diff --git a/cmd/dlv/dlv_test.go b/cmd/dlv/dlv_test.go
index 471daba9..98d02abc 100644
--- a/cmd/dlv/dlv_test.go
+++ b/cmd/dlv/dlv_test.go
@@ -2,7 +2,10 @@ package main
 
 import (
 	"bufio"
+	"bytes"
 	"flag"
+	"fmt"
+	"io/ioutil"
 	"os"
 	"os/exec"
 	"path/filepath"
@@ -96,3 +99,61 @@ func TestBuild(t *testing.T) {
 	client.Detach(true)
 	cmd.Wait()
 }
+
+func testIssue398(t *testing.T, dlvbin string, cmds []string) (stdout, stderr []byte) {
+	var stdoutBuf, stderrBuf bytes.Buffer
+	buildtestdir := filepath.Join(protest.FindFixturesDir(), "buildtest")
+	cmd := exec.Command(dlvbin, "debug")
+	cmd.Dir = buildtestdir
+	stdin, err := cmd.StdinPipe()
+	if err != nil {
+		t.Fatal(err)
+	}
+	cmd.Stdout = &stdoutBuf
+	cmd.Stderr = &stderrBuf
+	if err := cmd.Start(); err != nil {
+		t.Fatal(err)
+	}
+	for _, c := range cmds {
+		fmt.Fprintf(stdin, "%s\n", c)
+	}
+	// ignore "dlv debug" command error, it returns
+	// errors even after successful debug session.
+	cmd.Wait()
+	stdout, stderr = stdoutBuf.Bytes(), stderrBuf.Bytes()
+
+	debugbin := filepath.Join(buildtestdir, "debug")
+	_, err = os.Stat(debugbin)
+	if err == nil {
+		t.Errorf("running %q: file %v was not deleted\nstdout is %q, stderr is %q", cmds, debugbin, stdout, stderr)
+		return
+	}
+	if !os.IsNotExist(err) {
+		t.Errorf("running %q: %v\nstdout is %q, stderr is %q", cmds, err, stdout, stderr)
+		return
+	}
+	return
+}
+
+// TestIssue398 verifies that the debug executable is removed after exit.
+func TestIssue398(t *testing.T) {
+	tmpdir, err := ioutil.TempDir("", "TestIssue398")
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer os.RemoveAll(tmpdir)
+
+	dlvbin := filepath.Join(tmpdir, "dlv.exe")
+	out, err := exec.Command("go", "build", "-o", dlvbin, "github.com/derekparker/delve/cmd/dlv").CombinedOutput()
+	if err != nil {
+		t.Fatalf("go build -o %v github.com/derekparker/delve/cmd/dlv: %v\n%s", dlvbin, err, string(out))
+	}
+
+	testIssue398(t, dlvbin, []string{"exit"})
+
+	const hello = "hello world!"
+	stdout, _ := testIssue398(t, dlvbin, []string{"continue", "exit"})
+	if !strings.Contains(string(stdout), hello) {
+		t.Errorf("stdout %q should contain %q", stdout, hello)
+	}
+}
diff --git a/pkg/proc/native/proc.go b/pkg/proc/native/proc.go
index b9fa14a2..39428b75 100644
--- a/pkg/proc/native/proc.go
+++ b/pkg/proc/native/proc.go
@@ -3,7 +3,6 @@ package native
 import (
 	"fmt"
 	"go/ast"
-	"os"
 	"runtime"
 	"sync"
 
@@ -13,9 +12,8 @@ import (
 // Process represents all of the information the debugger
 // is holding onto regarding the process we are debugging.
 type Process struct {
-	bi      proc.BinaryInfo
-	pid     int         // Process Pid
-	Process *os.Process // Pointer to process struct for the actual process we are debugging
+	bi  proc.BinaryInfo
+	pid int // Process Pid
 
 	// Breakpoint table, holds information on breakpoints.
 	// Maps instruction address to Breakpoint struct.
@@ -388,13 +386,7 @@ func (dbp *Process) FindBreakpoint(pc uint64) (*proc.Breakpoint, bool) {
 
 // Returns a new Process struct.
 func initializeDebugProcess(dbp *Process, path string) (*Process, error) {
-	process, err := os.FindProcess(dbp.pid)
-	if err != nil {
-		return nil, err
-	}
-
-	dbp.Process = process
-	err = dbp.LoadInformation(path)
+	err := dbp.LoadInformation(path)
 	if err != nil {
 		return nil, err
 	}
@@ -461,6 +453,7 @@ func (dbp *Process) postExit() {
 	dbp.exited = true
 	close(dbp.ptraceChan)
 	close(dbp.ptraceDoneChan)
+	dbp.bi.Close()
 }
 
 func (dbp *Process) writeSoftwareBreakpoint(thread *Thread, addr uint64) error {
diff --git a/pkg/proc/native/proc_windows.go b/pkg/proc/native/proc_windows.go
index b98bac2e..9440e8e2 100644
--- a/pkg/proc/native/proc_windows.go
+++ b/pkg/proc/native/proc_windows.go
@@ -173,11 +173,25 @@ func (dbp *Process) Kill() error {
 	if !dbp.threads[dbp.pid].Stopped() {
 		return errors.New("process must be stopped in order to kill it")
 	}
+
+	p, err := os.FindProcess(dbp.pid)
+	if err != nil {
+		return err
+	}
+	defer p.Release()
+
 	// TODO: Should not have to ignore failures here,
 	// but some tests appear to Kill twice causing
 	// this to fail on second attempt.
 	_ = syscall.TerminateProcess(dbp.os.hProcess, 1)
-	dbp.exited = true
+
+	dbp.execPtraceFunc(func() {
+		dbp.waitForDebugEvent(waitBlocking)
+	})
+
+	p.Wait()
+
+	dbp.postExit()
 	return nil
 }
 
@@ -459,5 +473,7 @@ func killProcess(pid int) error {
 	if err != nil {
 		return err
 	}
+	defer p.Release()
+
 	return p.Kill()
 }