diff --git a/RELEASENOTES.md b/RELEASENOTES.md
index 43841a708c..5410c617cf 100644
--- a/RELEASENOTES.md
+++ b/RELEASENOTES.md
@@ -215,6 +215,9 @@
         ad view group
         ([#7344](https://github.com/google/ExoPlayer/issues/7344)),
         ([#8339](https://github.com/google/ExoPlayer/issues/8339)).
+    *   Fix a bug that could cause the next content position played after a
+        seek to snap back to the cue point of the preceding ad, rather than
+        the requested content position.
 *   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 f1fbad4c61..dab8daa3c1 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
@@ -1086,7 +1086,7 @@ import java.util.concurrent.atomic.AtomicBoolean;
 
     MediaPeriodId periodId;
     long periodPositionUs;
-    long requestedContentPosition;
+    long requestedContentPositionUs;
     boolean seekPositionAdjusted;
     @Nullable
     Pair<Object, Long> resolvedSeekPosition =
@@ -1105,17 +1105,17 @@ import java.util.concurrent.atomic.AtomicBoolean;
           getPlaceholderFirstMediaPeriodPosition(playbackInfo.timeline);
       periodId = firstPeriodAndPosition.first;
       periodPositionUs = firstPeriodAndPosition.second;
-      requestedContentPosition = C.TIME_UNSET;
+      requestedContentPositionUs = C.TIME_UNSET;
       seekPositionAdjusted = !playbackInfo.timeline.isEmpty();
     } else {
       // Update the resolved seek position to take ads into account.
       Object periodUid = resolvedSeekPosition.first;
-      long resolvedContentPosition = resolvedSeekPosition.second;
-      requestedContentPosition =
-          seekPosition.windowPositionUs == C.TIME_UNSET ? C.TIME_UNSET : resolvedContentPosition;
+      long resolvedContentPositionUs = resolvedSeekPosition.second;
+      requestedContentPositionUs =
+          seekPosition.windowPositionUs == C.TIME_UNSET ? C.TIME_UNSET : resolvedContentPositionUs;
       periodId =
           queue.resolveMediaPeriodIdForAds(
-              playbackInfo.timeline, periodUid, resolvedContentPosition);
+              playbackInfo.timeline, periodUid, resolvedContentPositionUs);
       if (periodId.isAd()) {
         playbackInfo.timeline.getPeriodByUid(periodId.periodUid, period);
         periodPositionUs =
@@ -1124,7 +1124,7 @@ import java.util.concurrent.atomic.AtomicBoolean;
                 : 0;
         seekPositionAdjusted = true;
       } else {
-        periodPositionUs = resolvedContentPosition;
+        periodPositionUs = resolvedContentPositionUs;
         seekPositionAdjusted = seekPosition.windowPositionUs == C.TIME_UNSET;
       }
     }
@@ -1175,11 +1175,11 @@ import java.util.concurrent.atomic.AtomicBoolean;
             /* newPeriodId= */ periodId,
             /* oldTimeline= */ playbackInfo.timeline,
             /* oldPeriodId= */ playbackInfo.periodId,
-            /* positionForTargetOffsetOverrideUs= */ requestedContentPosition);
+            /* positionForTargetOffsetOverrideUs= */ requestedContentPositionUs);
       }
     } finally {
       playbackInfo =
-          handlePositionDiscontinuity(periodId, periodPositionUs, requestedContentPosition);
+          handlePositionDiscontinuity(periodId, periodPositionUs, requestedContentPositionUs);
       if (seekPositionAdjusted) {
         playbackInfoUpdate.setPositionDiscontinuity(Player.DISCONTINUITY_REASON_SEEK_ADJUSTMENT);
       }
@@ -2242,6 +2242,12 @@ import java.util.concurrent.atomic.AtomicBoolean;
               ? emptyTrackSelectorResult
               : playingPeriodHolder.getTrackSelectorResult();
       staticMetadata = extractMetadataFromTrackSelectionArray(trackSelectorResult.selections);
+      // Ensure the media period queue requested content position matches the new playback info.
+      if (playingPeriodHolder != null
+          && playingPeriodHolder.info.requestedContentPositionUs != contentPositionUs) {
+        playingPeriodHolder.info =
+            playingPeriodHolder.info.copyWithRequestedContentPositionUs(contentPositionUs);
+      }
     } else if (!mediaPeriodId.equals(playbackInfo.periodId)) {
       // Reset previously kept track info if unprepared and the period changes.
       trackGroupArray = TrackGroupArray.EMPTY;
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 d4e66abf4e..55c3bd70ed 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
@@ -2682,6 +2682,64 @@ public final class ExoPlayerTest {
     assertThat(mediaSource.getCreatedMediaPeriods().get(3).adGroupIndex).isEqualTo(C.INDEX_UNSET);
   }
 
+  @Test
+  public void seekPastBufferingMidroll_playsAdAndThenContentFromSeekPosition() throws Exception {
+    long adGroupWindowTimeMs = 1_000;
+    long seekPositionMs = 95_000;
+    long contentDurationMs = 100_000;
+    AdPlaybackState adPlaybackState =
+        FakeTimeline.createAdPlaybackState(
+            /* adsPerAdGroup= */ 1,
+            /* adGroupTimesUs...= */ TimelineWindowDefinition
+                    .DEFAULT_WINDOW_OFFSET_IN_FIRST_PERIOD_US
+                + C.msToUs(adGroupWindowTimeMs));
+    Timeline timeline =
+        new FakeTimeline(
+            new TimelineWindowDefinition(
+                /* periodCount= */ 1,
+                /* id= */ 0,
+                /* isSeekable= */ true,
+                /* isDynamic= */ false,
+                /* durationUs= */ C.msToUs(contentDurationMs),
+                adPlaybackState));
+    AtomicBoolean hasCreatedAdMediaPeriod = new AtomicBoolean();
+    FakeMediaSource mediaSource =
+        new FakeMediaSource(timeline) {
+          @Override
+          public MediaPeriod createPeriod(
+              MediaPeriodId id, Allocator allocator, long startPositionUs) {
+            if (id.adGroupIndex == 0) {
+              hasCreatedAdMediaPeriod.set(true);
+            }
+            return super.createPeriod(id, allocator, startPositionUs);
+          }
+        };
+    SimpleExoPlayer player = new TestExoPlayerBuilder(context).build();
+    player.setMediaSource(mediaSource);
+    // Throw on the playback thread if the player position reaches a value that is just less than
+    // seek position. This ensures that playback stops and the assertion on the player position
+    // below fails, even if a long time passes between detecting the discontinuity and asserting.
+    player
+        .createMessage(
+            (messageType, payload) -> {
+              throw new IllegalStateException();
+            })
+        .setPosition(seekPositionMs - 1)
+        .send();
+    player.pause();
+    player.prepare();
+
+    // Block until the midroll has started buffering, then seek after the midroll before playing.
+    runMainLooperUntil(hasCreatedAdMediaPeriod::get);
+    player.seekTo(seekPositionMs);
+    player.play();
+
+    // When the ad finishes, the player position should be at or after the requested seek position.
+    TestPlayerRunHelper.runUntilPositionDiscontinuity(
+        player, Player.DISCONTINUITY_REASON_AD_INSERTION);
+    assertThat(player.getCurrentPosition()).isAtLeast(seekPositionMs);
+  }
+
   @Test
   public void repeatedSeeksToUnpreparedPeriodInSameWindowKeepsWindowSequenceNumber()
       throws Exception {