diff --git a/daemon/exec.go b/daemon/exec.go
index 464dd5db66..4dba7c9d47 100644
--- a/daemon/exec.go
+++ b/daemon/exec.go
@@ -135,6 +135,11 @@ func (d *Daemon) ContainerExecStart(name string, stdin io.ReadCloser, stdout io.
 	}
 
 	ec.Lock()
+	if ec.ExitCode != nil {
+		ec.Unlock()
+		return derr.ErrorCodeExecExited.WithArgs(ec.ID)
+	}
+
 	if ec.Running {
 		ec.Unlock()
 		return derr.ErrorCodeExecRunning.WithArgs(ec.ID)
@@ -214,7 +219,7 @@ func (d *Daemon) Exec(c *container.Container, execConfig *exec.Config, pipes *ex
 		exitStatus = 128
 	}
 
-	execConfig.ExitCode = exitStatus
+	execConfig.ExitCode = &exitStatus
 	execConfig.Running = false
 
 	return exitStatus, err
diff --git a/daemon/exec/exec.go b/daemon/exec/exec.go
index 5504ed3575..5536623191 100644
--- a/daemon/exec/exec.go
+++ b/daemon/exec/exec.go
@@ -18,7 +18,7 @@ type Config struct {
 	*runconfig.StreamConfig
 	ID            string
 	Running       bool
-	ExitCode      int
+	ExitCode      *int
 	ProcessConfig *execdriver.ProcessConfig
 	OpenStdin     bool
 	OpenStderr    bool
diff --git a/errors/daemon.go b/errors/daemon.go
index 278e712275..644dcdbe68 100644
--- a/errors/daemon.go
+++ b/errors/daemon.go
@@ -742,6 +742,15 @@ var (
 		HTTPStatusCode: http.StatusInternalServerError,
 	})
 
+	// ErrorCodeExecExited is generated when we try to start an exec
+	// but its already running.
+	ErrorCodeExecExited = errcode.Register(errGroup, errcode.ErrorDescriptor{
+		Value:          "EXECEXITED",
+		Message:        "Error: Exec command %s has already run",
+		Description:    "An attempt to start an 'exec' was made, but 'exec' was already run",
+		HTTPStatusCode: http.StatusConflict,
+	})
+
 	// ErrorCodeExecCantRun is generated when we try to start an exec
 	// but it failed for some reason.
 	ErrorCodeExecCantRun = errcode.Register(errGroup, errcode.ErrorDescriptor{
diff --git a/integration-cli/docker_api_exec_test.go b/integration-cli/docker_api_exec_test.go
index de504751de..c6ed847e24 100644
--- a/integration-cli/docker_api_exec_test.go
+++ b/integration-cli/docker_api_exec_test.go
@@ -8,6 +8,7 @@ import (
 	"fmt"
 	"net/http"
 	"strings"
+	"time"
 
 	"github.com/docker/docker/pkg/integration/checker"
 	"github.com/go-check/check"
@@ -66,33 +67,23 @@ func (s *DockerSuite) TestExecAPIStart(c *check.C) {
 	testRequires(c, DaemonIsLinux) // Uses pause/unpause but bits may be salvagable to Windows to Windows CI
 	dockerCmd(c, "run", "-d", "--name", "test", "busybox", "top")
 
-	startExec := func(id string, code int) {
-		resp, body, err := sockRequestRaw("POST", fmt.Sprintf("/exec/%s/start", id), strings.NewReader(`{"Detach": true}`), "application/json")
-		c.Assert(err, checker.IsNil)
-
-		b, err := readBody(body)
-		comment := check.Commentf("response body: %s", b)
-		c.Assert(err, checker.IsNil, comment)
-		c.Assert(resp.StatusCode, checker.Equals, code, comment)
-	}
-
 	id := createExec(c, "test")
-	startExec(id, http.StatusOK)
+	startExec(c, id, http.StatusOK)
 
 	id = createExec(c, "test")
 	dockerCmd(c, "stop", "test")
 
-	startExec(id, http.StatusNotFound)
+	startExec(c, id, http.StatusNotFound)
 
 	dockerCmd(c, "start", "test")
-	startExec(id, http.StatusNotFound)
+	startExec(c, id, http.StatusNotFound)
 
 	// make sure exec is created before pausing
 	id = createExec(c, "test")
 	dockerCmd(c, "pause", "test")
-	startExec(id, http.StatusConflict)
+	startExec(c, id, http.StatusConflict)
 	dockerCmd(c, "unpause", "test")
-	startExec(id, http.StatusOK)
+	startExec(c, id, http.StatusOK)
 }
 
 func (s *DockerSuite) TestExecAPIStartBackwardsCompatible(c *check.C) {
@@ -108,6 +99,30 @@ func (s *DockerSuite) TestExecAPIStartBackwardsCompatible(c *check.C) {
 	c.Assert(resp.StatusCode, checker.Equals, http.StatusOK, comment)
 }
 
+// #19362
+func (s *DockerSuite) TestExecAPIStartMultipleTimesError(c *check.C) {
+	dockerCmd(c, "run", "-d", "--name", "test", "busybox", "top")
+	execID := createExec(c, "test")
+	startExec(c, execID, http.StatusOK)
+
+	timeout := time.After(10 * time.Second)
+	var execJSON struct{ Running bool }
+	for {
+		select {
+		case <-timeout:
+			c.Fatal("timeout waiting for exec to start")
+		default:
+		}
+
+		inspectExec(c, execID, &execJSON)
+		if !execJSON.Running {
+			break
+		}
+	}
+
+	startExec(c, execID, http.StatusConflict)
+}
+
 func createExec(c *check.C, name string) string {
 	_, b, err := sockRequest("POST", fmt.Sprintf("/containers/%s/exec", name), map[string]interface{}{"Cmd": []string{"true"}})
 	c.Assert(err, checker.IsNil, check.Commentf(string(b)))
@@ -118,3 +133,22 @@ func createExec(c *check.C, name string) string {
 	c.Assert(json.Unmarshal(b, &createResp), checker.IsNil, check.Commentf(string(b)))
 	return createResp.ID
 }
+
+func startExec(c *check.C, id string, code int) {
+	resp, body, err := sockRequestRaw("POST", fmt.Sprintf("/exec/%s/start", id), strings.NewReader(`{"Detach": true}`), "application/json")
+	c.Assert(err, checker.IsNil)
+
+	b, err := readBody(body)
+	comment := check.Commentf("response body: %s", b)
+	c.Assert(err, checker.IsNil, comment)
+	c.Assert(resp.StatusCode, checker.Equals, code, comment)
+}
+
+func inspectExec(c *check.C, id string, out interface{}) {
+	resp, body, err := sockRequestRaw("GET", fmt.Sprintf("/exec/%s/json", id), nil, "")
+	c.Assert(err, checker.IsNil)
+	defer body.Close()
+	c.Assert(resp.StatusCode, checker.Equals, http.StatusOK)
+	err = json.NewDecoder(body).Decode(out)
+	c.Assert(err, checker.IsNil)
+}