diff --git a/airflow/docker.go b/airflow/docker.go
index f1596bdaa..1154ecb26 100644
--- a/airflow/docker.go
+++ b/airflow/docker.go
@@ -445,7 +445,7 @@ func getWebServerContainerId(airflowHome string) (string, error) {
 
 // Run creates using docker exec
 // inspired from https://github.com/docker/cli/tree/master/cli/command/container
-func Run(airflowHome string, args []string) error {
+func Run(airflowHome string, args []string, user string) error {
 	cli, err := client.NewClientWithOpts(client.FromEnv)
 
 	if err != nil {
@@ -454,9 +454,12 @@ func Run(airflowHome string, args []string) error {
 
 	execConfig := &types.ExecConfig{
 		AttachStdout: true,
-		Tty:          true,
 		Cmd:          args,
 	}
+	if user != "" {
+		execConfig.User = user
+	}
+
 	fmt.Printf("Running: %s\n", strings.Join(args, " "))
 	containerID, err := getWebServerContainerId(airflowHome)
 	if err != nil {
@@ -476,18 +479,11 @@ func Run(airflowHome string, args []string) error {
 
 	execStartCheck := types.ExecStartCheck{
 		Detach: execConfig.Detach,
-		Tty:    execConfig.Tty,
 	}
 
 	resp, _ := cli.ContainerExecAttach(context.Background(), execID, execStartCheck)
 
-	// Read stdout response from container
-	buf := new(bytes.Buffer)
-	_, err = buf.ReadFrom(resp.Reader)
-	s := buf.String()
-	fmt.Println(s)
-
-	return err
+	return docker.ExecPipe(resp, os.Stdin, os.Stdout, os.Stderr)
 }
 
 // Deploy pushes a new docker image
diff --git a/cmd/airflow.go b/cmd/airflow.go
index d59f837be..f986d16b1 100644
--- a/cmd/airflow.go
+++ b/cmd/airflow.go
@@ -76,6 +76,7 @@ func newDevRootCmd(client *houston.Client, out io.Writer) *cobra.Command {
 		newAirflowStopCmd(client, out),
 		newAirflowPSCmd(client, out),
 		newAirflowRunCmd(client, out),
+		newAirflowUpgradeCheckCmd(client, out),
 	)
 	return cmd
 }
@@ -216,6 +217,23 @@ func newAirflowRunCmd(client *houston.Client, out io.Writer) *cobra.Command {
 	return cmd
 }
 
+func newAirflowUpgradeCheckCmd(client *houston.Client, out io.Writer) *cobra.Command {
+	cmd := &cobra.Command{
+		Use:   "upgrade-check",
+		Short: "List DAG and config-level changes required to upgrade to Airflow 2.0",
+		Long:  "List DAG and config-level changes required to upgrade to Airflow 2.0",
+		// ignore PersistentPreRunE of root command
+		PersistentPreRunE: func(cmd *cobra.Command, args []string) error {
+			return nil
+		},
+		PreRunE:            ensureProjectDir,
+		RunE:               airflowUpgradeCheck,
+		Example:            RunExample,
+		DisableFlagParsing: true,
+	}
+	return cmd
+}
+
 func ensureProjectDir(cmd *cobra.Command, args []string) error {
 	isProjectDir, err := config.IsProjectDir(config.WorkingPath)
 	if err != nil {
@@ -370,7 +388,18 @@ func airflowRun(cmd *cobra.Command, args []string) error {
 
 	// Add airflow command, to simplify astro cli usage
 	args = append([]string{"airflow"}, args...)
-	return airflow.Run(config.WorkingPath, args)
+	// ignore last user parameter
+	return airflow.Run(config.WorkingPath, args, "")
+}
+
+// airflowUpgradeCheck
+func airflowUpgradeCheck(cmd *cobra.Command, args []string) error {
+	// Silence Usage as we have now validated command input
+	cmd.SilenceUsage = true
+
+	// Add airflow command, to simplify astro cli usage
+	args = append([]string{"bash", "-c", "pip install --no-deps 'apache-airflow-upgrade-check'; airflow upgrade_check"})
+	return airflow.Run(config.WorkingPath, args, "root")
 }
 
 func acceptableVersion(a string, list []string) bool {
diff --git a/cmd/airflow_test.go b/cmd/airflow_test.go
index 152300fb4..1c02da001 100644
--- a/cmd/airflow_test.go
+++ b/cmd/airflow_test.go
@@ -76,3 +76,9 @@ func TestNewAirflowRunCmd(t *testing.T) {
 	cmd := newAirflowRunCmd(client, os.Stdout)
 	assert.Nil(t, cmd.PersistentPreRunE(new(cobra.Command), []string{}))
 }
+
+func TestNewAirflowUpgradeCheckCmd(t *testing.T) {
+	client := houston.NewHoustonClient(httputil.NewHTTPClient())
+	cmd := newAirflowUpgradeCheckCmd(client, os.Stdout)
+	assert.Nil(t, cmd.PersistentPreRunE(new(cobra.Command), []string{}))
+}
diff --git a/docker/docker.go b/docker/docker.go
index 54a79b26c..820ed8f14 100644
--- a/docker/docker.go
+++ b/docker/docker.go
@@ -4,9 +4,11 @@ import (
 	"context"
 	"encoding/base64"
 	"encoding/json"
+	"io"
 	"os"
 	"os/exec"
 
+	"github.com/docker/docker/pkg/stdcopy"
 	"github.com/docker/docker/registry"
 
 	"github.com/docker/docker/pkg/jsonmessage"
@@ -139,3 +141,43 @@ func AirflowCommand(id string, airflowCommand string) string {
 	stringOut := string(out)
 	return stringOut
 }
+
+// ExecPipe does pipe stream into stdout/stdin and stderr
+// so now we can pipe out during exec'ing any commands inside container
+func ExecPipe(resp types.HijackedResponse, inStream io.Reader, outStream, errorStream io.Writer) error {
+	var err error
+	receiveStdout := make(chan error, 1)
+	if outStream != nil || errorStream != nil {
+		go func() {
+			// always do this because we are never tty
+			_, err = stdcopy.StdCopy(outStream, errorStream, resp.Reader)
+			receiveStdout <- err
+		}()
+	}
+
+	stdinDone := make(chan struct{})
+	go func() {
+		if inStream != nil {
+			io.Copy(resp.Conn, inStream)
+		}
+
+		if err := resp.CloseWrite(); err != nil {
+		}
+		close(stdinDone)
+	}()
+
+	select {
+	case err := <-receiveStdout:
+		if err != nil {
+			return err
+		}
+	case <-stdinDone:
+		if outStream != nil || errorStream != nil {
+			if err := <-receiveStdout; err != nil {
+				return err
+			}
+		}
+	}
+
+	return nil
+}
diff --git a/docker/docker_test.go b/docker/docker_test.go
index fe089f55c..241e9915a 100644
--- a/docker/docker_test.go
+++ b/docker/docker_test.go
@@ -1,6 +1,13 @@
 package docker
 
-import "testing"
+import (
+	"bufio"
+	"bytes"
+	"fmt"
+	"github.com/docker/docker/api/types"
+	"strings"
+	"testing"
+)
 
 func TestExecVersion(t *testing.T) {
 	err := Exec("version")
@@ -8,3 +15,23 @@ func TestExecVersion(t *testing.T) {
 		t.Error(err)
 	}
 }
+
+func TestExecPipe(t *testing.T) {
+	var buf bytes.Buffer
+	data := ""
+	resp := &types.HijackedResponse{Reader: bufio.NewReader(strings.NewReader(data))}
+	err := ExecPipe(*resp, &buf, &buf, &buf)
+	fmt.Println(buf.String())
+	if err != nil {
+		t.Error(err)
+	}
+}
+
+func TestExecPipeNils(t *testing.T) {
+	data := ""
+	resp := &types.HijackedResponse{Reader: bufio.NewReader(strings.NewReader(data))}
+	err := ExecPipe(*resp, nil, nil, nil)
+	if err != nil {
+		t.Error(err)
+	}
+}