diff --git a/web/web_test.go b/web/web_test.go
index cbcf15ffdc..e5ac162469 100644
--- a/web/web_test.go
+++ b/web/web_test.go
@@ -118,12 +118,10 @@ func TestReadyAndHealthy(t *testing.T) {
 		}
 	}()
 
-	// Give some time for the web goroutine to run since we need the server
-	// to be up before starting tests.
-	time.Sleep(5 * time.Second)
-
 	baseURL := "http://localhost" + port
 
+	waitForServerReady(t, baseURL, 5*time.Second)
+
 	resp, err := http.Get(baseURL + "/-/healthy")
 	require.NoError(t, err)
 	require.Equal(t, http.StatusOK, resp.StatusCode)
@@ -256,12 +254,10 @@ func TestRoutePrefix(t *testing.T) {
 		}
 	}()
 
-	// Give some time for the web goroutine to run since we need the server
-	// to be up before starting tests.
-	time.Sleep(5 * time.Second)
-
 	baseURL := "http://localhost" + port
 
+	waitForServerReady(t, baseURL+opts.RoutePrefix, 5*time.Second)
+
 	resp, err := http.Get(baseURL + opts.RoutePrefix + "/-/healthy")
 	require.NoError(t, err)
 	require.Equal(t, http.StatusOK, resp.StatusCode)
@@ -449,9 +445,9 @@ func TestShutdownWithStaleConnection(t *testing.T) {
 		close(closed)
 	}()
 
-	// Give some time for the web goroutine to run since we need the server
-	// to be up before starting tests.
-	time.Sleep(5 * time.Second)
+	baseURL := "http://localhost" + port
+
+	waitForServerReady(t, baseURL, 5*time.Second)
 
 	// Open a socket, and don't use it. This connection should then be closed
 	// after the ReadTimeout.
@@ -500,12 +496,10 @@ func TestHandleMultipleQuitRequests(t *testing.T) {
 		close(closed)
 	}()
 
-	// Give some time for the web goroutine to run since we need the server
-	// to be up before starting tests.
-	time.Sleep(5 * time.Second)
-
 	baseURL := opts.ExternalURL.Scheme + "://" + opts.ExternalURL.Host
 
+	waitForServerReady(t, baseURL, 5*time.Second)
+
 	start := make(chan struct{})
 	var wg sync.WaitGroup
 	for range 3 {
@@ -578,11 +572,10 @@ func TestAgentAPIEndPoints(t *testing.T) {
 		}
 	}()
 
-	// Give some time for the web goroutine to run since we need the server
-	// to be up before starting tests.
-	time.Sleep(5 * time.Second)
 	baseURL := "http://localhost" + port + "/api/v1"
 
+	waitForServerReady(t, "http://localhost"+port, 5*time.Second)
+
 	// Test for non-available endpoints in the Agent mode.
 	for path, methods := range map[string][]string{
 		"/labels":                      {http.MethodGet, http.MethodPost},
@@ -711,9 +704,7 @@ func TestMultipleListenAddresses(t *testing.T) {
 		}
 	}()
 
-	// Give some time for the web goroutine to run since we need the server
-	// to be up before starting tests.
-	time.Sleep(5 * time.Second)
+	waitForServerReady(t, "http://localhost"+port1, 5*time.Second)
 
 	// Set to ready.
 	webHandler.SetReady(Ready)
@@ -732,3 +723,24 @@ func TestMultipleListenAddresses(t *testing.T) {
 		cleanupTestResponse(t, resp)
 	}
 }
+
+// Give some time for the web goroutine to run since we need the server
+// to be up before starting tests.
+func waitForServerReady(t *testing.T, baseURL string, timeout time.Duration) {
+	t.Helper()
+
+	interval := 100 * time.Millisecond
+	deadline := time.Now().Add(timeout)
+
+	for time.Now().Before(deadline) {
+		resp, err := http.Get(baseURL + "/-/healthy")
+		if resp != nil {
+			cleanupTestResponse(t, resp)
+		}
+		if err == nil && resp.StatusCode == http.StatusOK {
+			return
+		}
+		time.Sleep(interval)
+	}
+	t.Fatalf("Server did not become ready within %v", timeout)
+}