diff --git a/RELEASENOTES.md b/RELEASENOTES.md
index 2ed1e79db3..08d9fb9e7f 100644
--- a/RELEASENOTES.md
+++ b/RELEASENOTES.md
@@ -252,6 +252,9 @@
         skipped but only after the preload timeout rather than instantly
         ([#8428](https://github.com/google/ExoPlayer/issues/8428)),
         ([#7832](https://github.com/google/ExoPlayer/issues/7832)).
+    *   Fix a regression that caused a short ad followed by another ad to be
+        skipped due to playback being stuck buffering waiting for the second ad
+        to load ([#8492](https://github.com/google/ExoPlayer/issues/8492)).
 *   FFmpeg extension:
     *   Link the FFmpeg library statically, saving 350KB in binary size on
         average.
diff --git a/library/core/src/main/java/com/google/android/exoplayer2/ExoPlayerImplInternal.java b/library/core/src/main/java/com/google/android/exoplayer2/ExoPlayerImplInternal.java
index d925e99055..5ce390404c 100644
--- a/library/core/src/main/java/com/google/android/exoplayer2/ExoPlayerImplInternal.java
+++ b/library/core/src/main/java/com/google/android/exoplayer2/ExoPlayerImplInternal.java
@@ -1729,8 +1729,13 @@ import java.util.concurrent.atomic.AtomicBoolean;
             ? livePlaybackSpeedControl.getTargetLiveOffsetUs()
             : C.TIME_UNSET;
     MediaPeriodHolder loadingHolder = queue.getLoadingPeriod();
-    boolean bufferedToEnd = loadingHolder.isFullyBuffered() && loadingHolder.info.isFinal;
-    return bufferedToEnd
+    boolean isBufferedToEnd = loadingHolder.isFullyBuffered() && loadingHolder.info.isFinal;
+    // Ad loader implementations may only load ad media once playback has nearly reached the ad, but
+    // it is possible for playback to be stuck buffering waiting for this. Therefore, we start
+    // playback regardless of buffered duration if we are waiting for an ad media period to prepare.
+    boolean isAdPendingPreparation = loadingHolder.info.id.isAd() && !loadingHolder.prepared;
+    return isBufferedToEnd
+        || isAdPendingPreparation
         || loadControl.shouldStartPlayback(
             getTotalBufferedDurationUs(),
             mediaClock.getPlaybackParameters().speed,
diff --git a/library/core/src/test/java/com/google/android/exoplayer2/ExoPlayerTest.java b/library/core/src/test/java/com/google/android/exoplayer2/ExoPlayerTest.java
index 55c3bd70ed..92eb6ffd03 100644
--- a/library/core/src/test/java/com/google/android/exoplayer2/ExoPlayerTest.java
+++ b/library/core/src/test/java/com/google/android/exoplayer2/ExoPlayerTest.java
@@ -4816,6 +4816,53 @@ public final class ExoPlayerTest {
         .blockUntilEnded(TIMEOUT_MS);
   }
 
+  @Test
+  public void shortAdFollowedByUnpreparedAd_playbackDoesNotGetStuck() throws Exception {
+    AdPlaybackState adPlaybackState =
+        FakeTimeline.createAdPlaybackState(/* adsPerAdGroup= */ 2, /* adGroupTimesUs...= */ 0);
+    long shortAdDurationMs = 1_000;
+    adPlaybackState =
+        adPlaybackState.withAdDurationsUs(new long[][] {{shortAdDurationMs, shortAdDurationMs}});
+    Timeline timeline =
+        new FakeTimeline(
+            new TimelineWindowDefinition(
+                /* periodCount= */ 1,
+                /* id= */ 0,
+                /* isSeekable= */ true,
+                /* isDynamic= */ false,
+                /* durationUs= */ C.msToUs(10000),
+                adPlaybackState));
+    // Simulate the second ad not being prepared.
+    FakeMediaSource mediaSource =
+        new FakeMediaSource(timeline, ExoPlayerTestRunner.VIDEO_FORMAT) {
+          @Override
+          protected MediaPeriod createMediaPeriod(
+              MediaPeriodId id,
+              TrackGroupArray trackGroupArray,
+              Allocator allocator,
+              MediaSourceEventListener.EventDispatcher mediaSourceEventDispatcher,
+              DrmSessionManager drmSessionManager,
+              DrmSessionEventListener.EventDispatcher drmEventDispatcher,
+              @Nullable TransferListener transferListener) {
+            return new FakeMediaPeriod(
+                trackGroupArray,
+                allocator,
+                FakeMediaPeriod.TrackDataFactory.singleSampleWithTimeUs(0),
+                mediaSourceEventDispatcher,
+                drmSessionManager,
+                drmEventDispatcher,
+                /* deferOnPrepared= */ id.adIndexInAdGroup == 1);
+          }
+        };
+    SimpleExoPlayer player = new TestExoPlayerBuilder(context).build();
+    player.setMediaSource(mediaSource);
+    player.prepare();
+    player.play();
+
+    // The player is not stuck in the buffering state.
+    TestPlayerRunHelper.runUntilPlaybackState(player, Player.STATE_READY);
+  }
+
   @Test
   public void moveMediaItem() throws Exception {
     TimelineWindowDefinition firstWindowDefinition =