diff --git a/components/supervisor/pkg/supervisor/ssh.go b/components/supervisor/pkg/supervisor/ssh.go
index 67aa96967df148..fe879592f07d0e 100644
--- a/components/supervisor/pkg/supervisor/ssh.go
+++ b/components/supervisor/pkg/supervisor/ssh.go
@@ -8,6 +8,7 @@ import (
 	"bufio"
 	"context"
 	"fmt"
+	"io/ioutil"
 	"net"
 	"os"
 	"os/exec"
@@ -85,7 +86,7 @@ func (s *sshServer) handleConn(ctx context.Context, conn net.Conn) {
 	}
 
 	args := []string{
-		"-iedD", "-f/dev/null",
+		"-ieD", "-f/dev/null",
 		"-oProtocol 2",
 		"-oAllowUsers gitpod",
 		"-oPasswordAuthentication no",
@@ -213,3 +214,36 @@ func writeSSHEnv(cfg *Config, envvars []string) error {
 
 	return nil
 }
+
+func configureSSHDefaultDir(cfg *Config) {
+	if cfg.RepoRoot == "" {
+		log.Error("cannot configure ssh default dir with empty repo root")
+		return
+	}
+	file, err := os.OpenFile("/home/gitpod/.bashrc", os.O_WRONLY|os.O_APPEND|os.O_CREATE, 0o644)
+	if err != nil {
+		log.WithError(err).Error("cannot write .bashrc")
+	}
+	defer file.Close()
+	if _, err := file.WriteString(fmt.Sprintf("\nif [[ -n $SSH_CONNECTION ]]; then cd \"%s\"; fi\n", cfg.RepoRoot)); err != nil {
+		log.WithError(err).Error("write .bashrc failed")
+	}
+}
+
+func configureSSHMessageOfTheDay() {
+	msg := []byte(`Welcome to Gitpod: Always ready to code. Try the following commands to get started:
+
+	gp tasks list         List all your defined tasks in .gitpod.yml
+	gp tasks attach       Attach your terminal to a workspace task
+
+	gp ports list         Lists workspace ports and their states
+	gp stop               Stop current workspace
+	gp help               To learn about the gp CLI commands
+
+For more information, see the Gitpod documentation: https://gitpod.io/docs
+`)
+
+	if err := ioutil.WriteFile("/etc/motd", msg, 0o644); err != nil {
+		log.WithError(err).Error("write /etc/motd failed")
+	}
+}
diff --git a/components/supervisor/pkg/supervisor/supervisor.go b/components/supervisor/pkg/supervisor/supervisor.go
index 37504bc44a3f28..a7ba8b6929a0b9 100644
--- a/components/supervisor/pkg/supervisor/supervisor.go
+++ b/components/supervisor/pkg/supervisor/supervisor.go
@@ -1234,7 +1234,8 @@ func startSSHServer(ctx context.Context, cfg *Config, wg *sync.WaitGroup, childP
 			log.WithError(err).Error("err creating SSH server")
 			return
 		}
-
+		configureSSHDefaultDir(cfg)
+		configureSSHMessageOfTheDay()
 		err = ssh.listenAndServe()
 		if err != nil {
 			log.WithError(err).Error("err starting SSH server")