diff --git a/end-to-end/cloud_init_test.go b/end-to-end/cloud_init_test.go
new file mode 100644
index 000000000..5862beecc
--- /dev/null
+++ b/end-to-end/cloud_init_test.go
@@ -0,0 +1,116 @@
+package endtoend_test
+
+import (
+	"context"
+	"os"
+	"path/filepath"
+	"strings"
+	"testing"
+	"time"
+
+	landscapeapi "github.com/canonical/landscape-hostagent-api"
+	"github.com/canonical/ubuntu-pro-for-wsl/common/golden"
+	"github.com/stretchr/testify/require"
+	wsl "github.com/ubuntu/gowsl"
+)
+
+func TestCloudInitIntegration(t *testing.T) {
+	currentFuncName := t.Name()
+
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	testSetup(t)
+	defer logWindowsAgentOnError(t)
+
+	landscape := NewLandscape(t, ctx)
+	writeUbuntuProRegistry(t, "LandscapeConfig", landscape.ClientConfig)
+
+	go landscape.Serve()
+	defer landscape.LogOnError(t)
+	defer landscape.Stop()
+
+	hostname, err := os.Hostname()
+	require.NoError(t, err, "Setup: could not test machine's hostname")
+
+	proToken := os.Getenv(proTokenEnv)
+	require.NotEmptyf(t, proToken, "Setup: environment variable %q should contain a valid pro token, but is empty", proTokenEnv)
+	writeUbuntuProRegistry(t, "UbuntuProToken", proToken)
+
+	cleanup := startAgent(t, ctx, currentFuncName)
+	defer cleanup()
+
+	info := landscape.RequireReceivedInfo(t, proToken, nil, hostname)
+
+	out, err := os.ReadFile(filepath.Join(golden.TestFixturePath(t), "user-data.yaml"))
+	require.NoError(t, err, "Setup: could not read cloud-init file")
+	cloudInitUserData := string(out)
+
+	err = landscape.service.SendCommand(ctx, info.UID, &landscapeapi.Command{
+		Cmd: &landscapeapi.Command_Install_{
+			Install: &landscapeapi.Command_Install{
+				Id:        strings.Split(referenceDistroAppx, ".")[1], // CanonicalGroupLimited.[UbuntuPreview]
+				Cloudinit: &cloudInitUserData,
+			},
+		},
+	})
+	require.NoError(t, err, "Setup: could not send install command")
+
+	distro := wsl.NewDistro(ctx, referenceDistro)
+
+	//nolint:errcheck // Nothing we can do about it
+	defer distro.Unregister()
+
+	require.Eventually(t, func() bool {
+		ok, err := distro.IsRegistered()
+		if err != nil {
+			t.Logf("could not determine if distro is registered: %v", err)
+			return false
+		}
+		return ok
+	}, time.Minute, time.Second, "Distro should have been registered")
+
+	defer logWslProServiceOnError(t, ctx, distro)
+
+	runCommand(t, ctx, time.Minute, distro, "cloud-init status --wait")
+
+	require.Eventually(t, func() bool {
+		attached, err := distroIsProAttached(t, ctx, distro)
+		if err != nil {
+			t.Logf("could not determine if distro is attached: %v", err)
+			return false
+		}
+		return attached
+	}, 10*time.Second, time.Second, "distro should have been Pro attached")
+
+	userName := runCommand(t, ctx, 10*time.Second, distro, "whoami")
+	require.Equal(t, "testuser", userName, "cloud-init should have configured the default user")
+
+	landscape.RequireReceivedInfo(t, proToken, []wsl.Distro{distro}, hostname)
+	landscape.RequireUninstallCommand(t, ctx, distro, info)
+}
+
+//nolint:revive // t always goes before ctx
+func runCommand(t *testing.T, ctx context.Context, timeout time.Duration, distro wsl.Distro, comand string) string {
+	t.Helper()
+
+	ctx, cancel := context.WithTimeout(ctx, timeout)
+	defer cancel()
+
+	out, err := distro.Command(ctx, comand).CombinedOutput()
+	if err == nil {
+		return string(out)
+	}
+
+	// We check the context to see if it was a timeout.
+	// This makes the error message easier to understand.
+
+	select {
+	case <-ctx.Done():
+		require.Fail(t, "Timed out waiting for cloud-init to finish")
+	default:
+	}
+
+	require.NoError(t, err, "could not determine if cloud-init is done: %s. Output: %s", out, out)
+	return ""
+}
diff --git a/end-to-end/landscape_utils_test.go b/end-to-end/landscape_utils_test.go
index 0331bdcec..759357348 100644
--- a/end-to-end/landscape_utils_test.go
+++ b/end-to-end/landscape_utils_test.go
@@ -109,7 +109,7 @@ func (l landscape) Stop() {
 }
 
 // RequireReceivedInfo checks that a connection to Landscape was made and the proper information was sent.
-func (l landscape) RequireReceivedInfo(t *testing.T, wantToken string, wantDistro gowsl.Distro, wantHostname string) landscapemockservice.HostInfo {
+func (l landscape) RequireReceivedInfo(t *testing.T, wantToken string, wantDistros []gowsl.Distro, wantHostname string) landscapemockservice.HostInfo {
 	t.Helper()
 
 	require.Eventually(t, func() bool {
@@ -122,9 +122,12 @@ func (l landscape) RequireReceivedInfo(t *testing.T, wantToken string, wantDistr
 	// Validate token
 	require.Equal(t, wantToken, info.Token, "Landscape did not receive the right pro token")
 
-	// Validate distro
-	require.Len(t, info.Instances, 1, "Landscape did not receive the right number of distros")
-	require.Equal(t, wantDistro.Name(), info.Instances[0].ID, "Landscape did not receive the right distro name from the agent")
+	// Validate distros
+	gotDistros := make([]string, 0)
+	for _, instance := range info.Instances {
+		gotDistros = append(gotDistros, instance.ID)
+	}
+	require.ElementsMatch(t, wantDistros, gotDistros, "Landscape did not receive the right distros")
 
 	// Validate hostname
 	require.Equal(t, wantHostname, info.Hostname, "Landscape did not receive the right hostname from the agent")
diff --git a/end-to-end/manual_token_input_test.go b/end-to-end/manual_token_input_test.go
index 48a3b29f3..73b0c0b96 100644
--- a/end-to-end/manual_token_input_test.go
+++ b/end-to-end/manual_token_input_test.go
@@ -63,7 +63,7 @@ func TestManualTokenInput(t *testing.T) {
 
 			defer logWslProServiceOnError(t, ctx, d)
 
-			out, err := d.Command(ctx, "exit 0").CombinedOutput()
+			out, err := d.Command(ctx, "cloud-init status --wait").CombinedOutput()
 			require.NoErrorf(t, err, "Setup: could not wake distro up: %v. %s", err, out)
 
 			// ... or after registration, but never both.
@@ -94,7 +94,7 @@ func TestManualTokenInput(t *testing.T) {
 				return attached
 			}, maxTimeout, time.Second, "distro should have been Pro attached")
 
-			info := landscape.RequireReceivedInfo(t, os.Getenv(proTokenEnv), d, hostname)
+			info := landscape.RequireReceivedInfo(t, os.Getenv(proTokenEnv), []wsl.Distro{d}, hostname)
 			landscape.RequireUninstallCommand(t, ctx, d, info)
 		})
 	}
diff --git a/end-to-end/organization_token_test.go b/end-to-end/organization_token_test.go
index fc0f26022..d41504d47 100644
--- a/end-to-end/organization_token_test.go
+++ b/end-to-end/organization_token_test.go
@@ -65,7 +65,7 @@ func TestOrganizationProvidedToken(t *testing.T) {
 
 			defer logWslProServiceOnError(t, ctx, d)
 
-			out, err := d.Command(ctx, "exit 0").CombinedOutput()
+			out, err := d.Command(ctx, "cloud-init status --wait").CombinedOutput()
 			require.NoErrorf(t, err, "Setup: could not wake distro up: %v. %s", err, out)
 
 			if tc.whenToken == afterDistroRegistration {
@@ -99,7 +99,7 @@ func TestOrganizationProvidedToken(t *testing.T) {
 				return attached
 			}, maxTimeout, time.Second, "distro should have been Pro attached")
 
-			info := landscape.RequireReceivedInfo(t, proToken, d, hostname)
+			info := landscape.RequireReceivedInfo(t, proToken, []wsl.Distro{d}, hostname)
 			landscape.RequireUninstallCommand(t, ctx, d, info)
 		})
 	}
diff --git a/end-to-end/purchase_test.go b/end-to-end/purchase_test.go
index b6d599750..3a2edf8aa 100644
--- a/end-to-end/purchase_test.go
+++ b/end-to-end/purchase_test.go
@@ -121,7 +121,7 @@ func TestPurchase(t *testing.T) {
 
 			defer logWslProServiceOnError(t, ctx, d)
 
-			out, err := d.Command(ctx, "exit 0").CombinedOutput()
+			out, err := d.Command(ctx, "cloud-init status --wait").CombinedOutput()
 			require.NoErrorf(t, err, "Setup: could not wake distro up: %v. %s", err, out)
 
 			// ... or after registration, but never both.
@@ -153,7 +153,7 @@ func TestPurchase(t *testing.T) {
 				return attached
 			}, maxTimeout, time.Second, "distro should have been Pro attached")
 
-			landscape.RequireReceivedInfo(t, token, d, hostname)
+			landscape.RequireReceivedInfo(t, token, []wsl.Distro{d}, hostname)
 			// Skipping because we know it to be broken
 			// See https://warthogs.atlassian.net/browse/UDENG-1810
 			//
diff --git a/end-to-end/testdata/TestCloudInitIntegration/user-data.yaml b/end-to-end/testdata/TestCloudInitIntegration/user-data.yaml
new file mode 100644
index 000000000..2857b3486
--- /dev/null
+++ b/end-to-end/testdata/TestCloudInitIntegration/user-data.yaml
@@ -0,0 +1,13 @@
+#cloud-config
+users:
+  - name: testuser
+    gecos: Test User
+    sudo: ALL=(ALL) NOPASSWD:ALL
+    groups: [adm,dialout,cdrom,floppy,sudo,audio,dip,video,plugdev,users,netdev]
+    shell: /bin/bash
+write_files:
+- path: /etc/wsl.conf
+  append: true
+  content: |
+    [user]
+    default=testuser
diff --git a/gui/packages/ubuntupro/end_to_end/end_to_end_test.dart b/gui/packages/ubuntupro/end_to_end/end_to_end_test.dart
index 8615bd1d7..3a509ddc7 100644
--- a/gui/packages/ubuntupro/end_to_end/end_to_end_test.dart
+++ b/gui/packages/ubuntupro/end_to_end/end_to_end_test.dart
@@ -25,6 +25,7 @@ void main(List<String> args) {
 
   const testCases = {
     'TestOrganizationProvidedToken': testOrganizationProvidedToken,
+    'TestCloudInitIntegration': testOrganizationProvidedToken,
     'TestManualTokenInput': testManualTokenInput,
     'TestPurchase': testPurchase,
   };