diff --git a/actix-http/src/config.rs b/actix-http/src/config.rs
index 0e01e8748..6661e18f3 100644
--- a/actix-http/src/config.rs
+++ b/actix-http/src/config.rs
@@ -326,7 +326,7 @@ mod notify_on_drop {
 mod tests {
     use super::*;
 
-    use actix_rt::task::yield_now;
+    use actix_rt::{task::yield_now, time::sleep};
 
     #[actix_rt::test]
     async fn test_date_service_update() {
@@ -350,7 +350,14 @@ mod tests {
         assert_ne!(buf1, buf2);
 
         drop(settings);
-        assert!(notify_on_drop::is_dropped());
+
+        // Ensure the task will drop eventually
+        let mut times = 0;
+        while !notify_on_drop::is_dropped() {
+            sleep(Duration::from_millis(100)).await;
+            times += 1;
+            assert!(times < 10, "Timeout waiting for task drop");
+        }
     }
 
     #[actix_rt::test]
@@ -372,7 +379,14 @@ mod tests {
         assert!(!notify_on_drop::is_dropped());
 
         drop(service);
-        assert!(notify_on_drop::is_dropped());
+
+        // Ensure the task will drop eventually
+        let mut times = 0;
+        while !notify_on_drop::is_dropped() {
+            sleep(Duration::from_millis(100)).await;
+            times += 1;
+            assert!(times < 10, "Timeout waiting for task drop");
+        }
     }
 
     #[test]