diff --git a/internal/tests/integration_test.go b/internal/tests/integration_test.go
index 0c5874a..9b2333a 100644
--- a/internal/tests/integration_test.go
+++ b/internal/tests/integration_test.go
@@ -68,7 +68,7 @@ func TestSingleVM(t *testing.T) {
 		if err != nil {
 			t.Fatal(err)
 		}
-		return len(logLines) > 0
+		return len(logLines) >= 1000
 	}), "failed to wait for logs to become available")
 	logLines, err := devClient.VMs().Logs(context.Background(), "test-vm")
 	if err != nil {
@@ -78,7 +78,7 @@ func TestSingleVM(t *testing.T) {
 	for i := 1; i <= 1000; i++ {
 		expectedLogs = append(expectedLogs, strconv.Itoa(i))
 	}
-	assert.Equal(t, expectedLogs, logLines)
+	assert.Contains(t, strings.Join(logLines, "\n"), strings.Join(expectedLogs, "\n"))
 
 	// Ensure that the VM exists on disk before deleting it
 	require.True(t, hasVMByPredicate(t, func(info tart.VMInfo) bool {
@@ -416,17 +416,17 @@ func TestHostDirs(t *testing.T) {
 		logLines, err = devClient.VMs().Logs(context.Background(), vmName)
 		require.NoError(t, err)
 
-		return len(logLines) > 0
+		return len(logLines) >= 4
 	}), "failed to wait for logs to become available")
 
 	fmt.Println(logLines)
 
-	require.EqualValues(t, []string{
+	require.Contains(t, strings.Join(logLines, "\n"), strings.Join([]string{
 		"Read-write mount exists",
 		"Read-only mount exists",
 		"Failed to create a file in read-only mount",
 		"Successfully created a file in read-write mount",
-	}, logLines)
+	}, "\n"))
 	require.FileExists(t, filepath.Join(dirToMount, "test-rw.txt"))
 	require.NoFileExists(t, filepath.Join(dirToMount, "test-ro.txt"))
 }
diff --git a/internal/worker/vmmanager/vm.go b/internal/worker/vmmanager/vm.go
index 2fd4f62..a81817c 100644
--- a/internal/worker/vmmanager/vm.go
+++ b/internal/worker/vmmanager/vm.go
@@ -316,31 +316,15 @@ func (vm *VM) shell(
 	env map[string]string,
 	consumeLine func(line string),
 ) error {
-	ip, err := vm.IP(ctx)
-	if err != nil {
-		return fmt.Errorf("%w to get IP", ErrVMFailed)
-	}
+	var sess *ssh.Session
 
-	var netConn net.Conn
-
-	addr := ip + ":22"
-
-	if err := retry.Do(func() error {
-		dialer := net.Dialer{}
-
-		netConn, err = dialer.DialContext(ctx, "tcp", addr)
-
-		return err
-	}, retry.Context(ctx)); err != nil {
-		return fmt.Errorf("%w to dial: %v", ErrVMFailed, err)
-	}
-
-	// set default user and password if not provided
+	// Set default user and password if not provided
 	if sshUser == "" && sshPassword == "" {
 		sshUser = "admin"
 		sshPassword = "admin"
 	}
 
+	// Configure SSH client
 	sshConfig := &ssh.ClientConfig{
 		HostKeyCallback: func(hostname string, remote net.Addr, key ssh.PublicKey) error {
 			return nil
@@ -351,15 +335,40 @@ func (vm *VM) shell(
 		},
 	}
 
-	sshConn, chans, reqs, err := ssh.NewClientConn(netConn, addr, sshConfig)
-	if err != nil {
-		return fmt.Errorf("%w to connect via SSH: %v", ErrVMFailed, err)
-	}
-	cli := ssh.NewClient(sshConn, chans, reqs)
+	if err := retry.Do(func() error {
+		ip, err := vm.IP(ctx)
+		if err != nil {
+			return fmt.Errorf("failed to get VM's IP: %w", err)
+		}
 
-	sess, err := cli.NewSession()
-	if err != nil {
-		return fmt.Errorf("%w: failed to open SSH session: %v", ErrVMFailed, err)
+		addr := ip + ":22"
+
+		dialer := net.Dialer{
+			Timeout: 5 * time.Second,
+		}
+
+		netConn, err := dialer.DialContext(ctx, "tcp", addr)
+		if err != nil {
+			return fmt.Errorf("failed to dial %s: %w", addr, err)
+		}
+
+		sshConn, chans, reqs, err := ssh.NewClientConn(netConn, addr, sshConfig)
+		if err != nil {
+			return fmt.Errorf("SSH handshake with %s failed: %w", addr, err)
+		}
+
+		sshClient := ssh.NewClient(sshConn, chans, reqs)
+
+		sess, err = sshClient.NewSession()
+		if err != nil {
+			return fmt.Errorf("failed to open an SSH session on %s: %w", addr, err)
+		}
+
+		return nil
+	}, retry.Context(ctx), retry.OnRetry(func(n uint, err error) {
+		consumeLine(fmt.Sprintf("attempt %d to establish SSH connection failed: %v", n, err))
+	})); err != nil {
+		return fmt.Errorf("failed to establish SSH connection: %w", err)
 	}
 
 	// Log output from the virtual machine