diff --git a/enterprise/cli/server_test.go b/enterprise/cli/server_test.go
new file mode 100644
index 0000000000..b70d6eab3c
--- /dev/null
+++ b/enterprise/cli/server_test.go
@@ -0,0 +1,52 @@
+package cli_test
+
+import (
+	"fmt"
+	"io"
+	"net/http"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/cli/clitest"
+	"github.com/coder/coder/v2/enterprise/cli"
+	"github.com/coder/coder/v2/testutil"
+)
+
+// TestServer runs the enterprise server command
+// and waits for /healthz to return "OK".
+func TestServer(t *testing.T) {
+	t.Parallel()
+
+	var root cli.RootCmd
+	cmd, err := root.Command(root.EnterpriseSubcommands())
+	require.NoError(t, err)
+	port := randomPort(t)
+	inv, _ := clitest.NewWithCommand(t, cmd,
+		"server",
+		"--in-memory",
+		"--http-address", fmt.Sprintf(":%d", port),
+		"--access-url", "http://example.com",
+	)
+	waiter := clitest.StartWithWaiter(t, inv)
+	require.Eventually(t, func() bool {
+		reqCtx := testutil.Context(t, testutil.IntervalMedium)
+		req, err := http.NewRequestWithContext(reqCtx, http.MethodGet, fmt.Sprintf("http://localhost:%d/healthz", port), nil)
+		if err != nil {
+			panic(err)
+		}
+		resp, err := http.DefaultClient.Do(req)
+		if err != nil {
+			t.Log("/healthz not ready yet")
+			return false
+		}
+		defer resp.Body.Close()
+		bs, err := io.ReadAll(resp.Body)
+		if err != nil {
+			panic(err)
+		}
+		return assert.Equal(t, "OK", string(bs))
+	}, testutil.WaitShort, testutil.IntervalMedium)
+	waiter.Cancel()
+}