diff --git a/integration/auth_web_flow_test.go b/integration/auth_web_flow_test.go
new file mode 100644
index 00000000..55d0fb49
--- /dev/null
+++ b/integration/auth_web_flow_test.go
@@ -0,0 +1,192 @@
+package integration
+
+import (
+	"context"
+	"errors"
+	"fmt"
+	"io"
+	"log"
+	"net/http"
+	"net/url"
+	"strings"
+	"testing"
+)
+
+var errParseAuthPage = errors.New("failed to parse auth page")
+
+type AuthWebFlowScenario struct {
+	*Scenario
+}
+
+func TestAuthWebFlowAuthenticationPingAll(t *testing.T) {
+	IntegrationSkip(t)
+
+	baseScenario, err := NewScenario()
+	if err != nil {
+		t.Errorf("failed to create scenario: %s", err)
+	}
+
+	scenario := AuthWebFlowScenario{
+		Scenario: baseScenario,
+	}
+
+	spec := map[string]int{
+		"namespace1": len(TailscaleVersions),
+		"namespace2": len(TailscaleVersions),
+	}
+
+	err = scenario.CreateHeadscaleEnv(spec)
+	if err != nil {
+		t.Errorf("failed to create headscale environment: %s", err)
+	}
+
+	allClients, err := scenario.ListTailscaleClients()
+	if err != nil {
+		t.Errorf("failed to get clients: %s", err)
+	}
+
+	allIps, err := scenario.ListTailscaleClientsIPs()
+	if err != nil {
+		t.Errorf("failed to get clients: %s", err)
+	}
+
+	err = scenario.WaitForTailscaleSync()
+	if err != nil {
+		t.Errorf("failed wait for tailscale clients to be in sync: %s", err)
+	}
+
+	success := 0
+
+	for _, client := range allClients {
+		for _, ip := range allIps {
+			err := client.Ping(ip.String())
+			if err != nil {
+				t.Errorf("failed to ping %s from %s: %s", ip, client.Hostname(), err)
+			} else {
+				success++
+			}
+		}
+	}
+
+	t.Logf("%d successful pings out of %d", success, len(allClients)*len(allIps))
+
+	err = scenario.Shutdown()
+	if err != nil {
+		t.Errorf("failed to tear down scenario: %s", err)
+	}
+}
+
+func (s *AuthWebFlowScenario) CreateHeadscaleEnv(namespaces map[string]int) error {
+	err := s.StartHeadscale()
+	if err != nil {
+		return err
+	}
+
+	err = s.Headscale().WaitForReady()
+	if err != nil {
+		return err
+	}
+
+	for namespaceName, clientCount := range namespaces {
+		log.Printf("creating namespace %s with %d clients", namespaceName, clientCount)
+		err = s.CreateNamespace(namespaceName)
+		if err != nil {
+			return err
+		}
+
+		err = s.CreateTailscaleNodesInNamespace(namespaceName, "all", clientCount)
+		if err != nil {
+			return err
+		}
+
+		err = s.runTailscaleUp(namespaceName, s.Headscale().GetEndpoint())
+		if err != nil {
+			return err
+		}
+	}
+
+	return nil
+}
+
+func (s *AuthWebFlowScenario) runTailscaleUp(
+	namespaceStr, loginServer string,
+) error {
+	log.Printf("running tailscale up for namespace %s", namespaceStr)
+	if namespace, ok := s.namespaces[namespaceStr]; ok {
+		for _, client := range namespace.Clients {
+			namespace.joinWaitGroup.Add(1)
+
+			go func(c TailscaleClient) {
+				defer namespace.joinWaitGroup.Done()
+
+				// TODO(juanfont): error handle this
+				loginURL, err := c.UpWithLoginURL(loginServer)
+				if err != nil {
+					log.Printf("failed to run tailscale up: %s", err)
+				}
+
+				err = s.runHeadscaleRegister(namespaceStr, loginURL)
+				if err != nil {
+					log.Printf("failed to register client: %s", err)
+				}
+
+				err = c.WaitForReady()
+				if err != nil {
+					log.Printf("error waiting for client %s to be ready: %s", c.Hostname(), err)
+				}
+			}(client)
+		}
+		namespace.joinWaitGroup.Wait()
+
+		return nil
+	}
+
+	return fmt.Errorf("failed to up tailscale node: %w", errNoNamespaceAvailable)
+}
+
+func (s *AuthWebFlowScenario) runHeadscaleRegister(namespaceStr string, loginURL *url.URL) error {
+	log.Printf("loginURL: %s", loginURL)
+	loginURL.Host = fmt.Sprintf("%s:8080", s.Headscale().GetIP())
+	loginURL.Scheme = "http"
+
+	httpClient := &http.Client{}
+	ctx := context.Background()
+	req, _ := http.NewRequestWithContext(ctx, http.MethodGet, loginURL.String(), nil)
+	resp, err := httpClient.Do(req)
+	if err != nil {
+		return err
+	}
+
+	body, err := io.ReadAll(resp.Body)
+	if err != nil {
+		return err
+	}
+
+	defer resp.Body.Close()
+
+	// see api.go HTML template
+	codeSep := strings.Split(string(body), "</code>")
+	if len(codeSep) != 2 {
+		return errParseAuthPage
+	}
+
+	keySep := strings.Split(codeSep[0], "key ")
+	if len(keySep) != 2 {
+		return errParseAuthPage
+	}
+	key := keySep[1]
+	log.Printf("registering node %s", key)
+
+	if headscale, ok := s.controlServers["headscale"]; ok {
+		_, err = headscale.Execute([]string{"headscale", "-n", namespaceStr, "nodes", "register", "--key", key})
+		if err != nil {
+			log.Printf("failed to register node: %s", err)
+
+			return err
+		}
+
+		return nil
+	}
+
+	return fmt.Errorf("failed to find headscale: %w", errNoHeadscaleAvailable)
+}