diff --git a/RELEASENOTES.md b/RELEASENOTES.md
index 06fd3cf799..116c2967c9 100644
--- a/RELEASENOTES.md
+++ b/RELEASENOTES.md
@@ -21,6 +21,9 @@
     *   Remove `extension-jobdispatcher` module. Use the `extension-workmanager`
         module instead.
 *   IMA extension:
+    *   Fix a bug where playback could get stuck when seeking into a playlist
+        item with ads, if the preroll ad had preloaded but the window position
+        of the seek should instead trigger playback of a midroll.
     *   Fix a bug with playback of ads in playlists, where the incorrect period
         index was used when deciding whether to trigger playback of an ad after
         a seek.
diff --git a/extensions/ima/src/main/java/com/google/android/exoplayer2/ext/ima/AdTagLoader.java b/extensions/ima/src/main/java/com/google/android/exoplayer2/ext/ima/AdTagLoader.java
index 3984d586df..39f9f36fd4 100644
--- a/extensions/ima/src/main/java/com/google/android/exoplayer2/ext/ima/AdTagLoader.java
+++ b/extensions/ima/src/main/java/com/google/android/exoplayer2/ext/ima/AdTagLoader.java
@@ -341,11 +341,25 @@ import java.util.Map;
 
     boolean playWhenReady = player.getPlayWhenReady();
     onTimelineChanged(player.getCurrentTimeline(), Player.TIMELINE_CHANGE_REASON_SOURCE_UPDATE);
-    if (!AdPlaybackState.NONE.equals(adPlaybackState)
-        && adsManager != null
-        && imaPausedContent
-        && playWhenReady) {
-      adsManager.resume();
+    @Nullable AdsManager adsManager = this.adsManager;
+    if (!AdPlaybackState.NONE.equals(adPlaybackState) && adsManager != null && imaPausedContent) {
+      // Check whether the current ad break matches the expected ad break based on the current
+      // position. If not, discard the current ad break so that the correct ad break can load.
+      long contentPositionMs = getContentPeriodPositionMs(player, timeline, period);
+      int adGroupForPositionIndex =
+          adPlaybackState.getAdGroupIndexForPositionUs(
+              C.msToUs(contentPositionMs), C.msToUs(contentDurationMs));
+      if (adGroupForPositionIndex != C.INDEX_UNSET
+          && imaAdInfo != null
+          && imaAdInfo.adGroupIndex != adGroupForPositionIndex) {
+        if (configuration.debugModeEnabled) {
+          Log.d(TAG, "Discarding preloaded ad " + imaAdInfo);
+        }
+        adsManager.discardAdBreak();
+      }
+      if (playWhenReady) {
+        adsManager.resume();
+      }
     }
   }