diff --git a/core/shared/src/main/scala/cats/effect/IO.scala b/core/shared/src/main/scala/cats/effect/IO.scala
index 7138a0b915f..0c51d9da36f 100644
--- a/core/shared/src/main/scala/cats/effect/IO.scala
+++ b/core/shared/src/main/scala/cats/effect/IO.scala
@@ -819,9 +819,12 @@ sealed abstract class IO[+A] private () extends IOPlatform[A] {
    */
   def timeoutTo[A2 >: A](duration: Duration, fallback: IO[A2]): IO[A2] = {
     handleDuration[IO[A2]](duration, this) { finiteDuration =>
-      race(IO.sleep(finiteDuration)).flatMap {
-        case Right(_) => fallback
-        case Left(value) => IO.pure(value)
+      IO.uncancelable { poll =>
+        poll(racePair(IO.sleep(finiteDuration))) flatMap {
+          case Left((oc, f)) => f.cancel *> oc.embed(poll(IO.canceled) *> IO.never)
+          case Right((f, _)) =>
+            f.cancel *> f.join.flatMap { oc => oc.fold(fallback, IO.raiseError, identity) }
+        }
       }
     }
   }
diff --git a/kernel/shared/src/main/scala/cats/effect/kernel/GenTemporal.scala b/kernel/shared/src/main/scala/cats/effect/kernel/GenTemporal.scala
index 56d6d0d2702..5ed9f8d4518 100644
--- a/kernel/shared/src/main/scala/cats/effect/kernel/GenTemporal.scala
+++ b/kernel/shared/src/main/scala/cats/effect/kernel/GenTemporal.scala
@@ -91,9 +91,13 @@ trait GenTemporal[F[_], E] extends GenConcurrent[F, E] with Clock[F] {
     handleDuration(duration, fa)(timeoutTo(fa, _, fallback))
 
   protected def timeoutTo[A](fa: F[A], duration: FiniteDuration, fallback: F[A]): F[A] =
-    flatMap(race(fa, sleep(duration))) {
-      case Left(a) => pure(a)
-      case Right(_) => fallback
+    uncancelable { poll =>
+      implicit val F: GenTemporal[F, E] = this
+
+      poll(racePair(fa, sleep(duration))) flatMap {
+        case Left((oc, f)) => f.cancel *> oc.embed(poll(F.canceled) *> F.never)
+        case Right((f, _)) => f.cancel *> f.join.flatMap { oc => oc.embed(fallback) }
+      }
     }
 
   /**
@@ -115,9 +119,16 @@ trait GenTemporal[F[_], E] extends GenConcurrent[F, E] with Clock[F] {
 
   protected def timeout[A](fa: F[A], duration: FiniteDuration)(
       implicit ev: TimeoutException <:< E): F[A] = {
-    flatMap(race(fa, sleep(duration))) {
-      case Left(a) => pure(a)
-      case Right(_) => raiseError[A](ev(new TimeoutException(duration.toString())))
+    uncancelable { poll =>
+      implicit val F: GenTemporal[F, E] = this
+
+      poll(racePair(fa, sleep(duration))) flatMap {
+        case Left((oc, f)) => f.cancel *> oc.embed(poll(F.canceled) *> F.never)
+        case Right((f, _)) =>
+          f.cancel *> f.join.flatMap { oc =>
+            oc.embed(raiseError[A](ev(new TimeoutException(duration.toString()))))
+          }
+      }
     }
   }