diff --git a/Userland/Libraries/LibVideo/Containers/Demuxer.h b/Userland/Libraries/LibVideo/Containers/Demuxer.h
index 1a2d2355d2..0915b8685e 100644
--- a/Userland/Libraries/LibVideo/Containers/Demuxer.h
+++ b/Userland/Libraries/LibVideo/Containers/Demuxer.h
@@ -29,7 +29,9 @@ public:
     }
 
     // Returns the timestamp of the keyframe that was seeked to.
-    virtual DecoderErrorOr<Time> seek_to_most_recent_keyframe(Track track, Time timestamp) = 0;
+    // The value is `Optional` to allow the demuxer to decide not to seek so that it can keep its position
+    // in the case that the timestamp is closer to the current time than the nearest keyframe.
+    virtual DecoderErrorOr<Optional<Time>> seek_to_most_recent_keyframe(Track track, Time timestamp, Optional<Time> earliest_available_sample = OptionalNone()) = 0;
 
     virtual DecoderErrorOr<Time> duration() = 0;
 
diff --git a/Userland/Libraries/LibVideo/Containers/Matroska/MatroskaDemuxer.cpp b/Userland/Libraries/LibVideo/Containers/Matroska/MatroskaDemuxer.cpp
index 62dbb1625b..674a6428ac 100644
--- a/Userland/Libraries/LibVideo/Containers/Matroska/MatroskaDemuxer.cpp
+++ b/Userland/Libraries/LibVideo/Containers/Matroska/MatroskaDemuxer.cpp
@@ -5,6 +5,7 @@
  */
 
 #include "MatroskaDemuxer.h"
+#include "AK/Debug.h"
 
 namespace Video::Matroska {
 
@@ -53,7 +54,7 @@ DecoderErrorOr<MatroskaDemuxer::TrackStatus*> MatroskaDemuxer::get_track_status(
     return &m_track_statuses.get(track).release_value();
 }
 
-DecoderErrorOr<Time> MatroskaDemuxer::seek_to_most_recent_keyframe(Track track, Time timestamp)
+DecoderErrorOr<Optional<Time>> MatroskaDemuxer::seek_to_most_recent_keyframe(Track track, Time timestamp, Optional<Time> earliest_available_sample)
 {
     // Removing the track status will cause us to start from the beginning.
     if (timestamp.is_zero()) {
@@ -62,7 +63,22 @@ DecoderErrorOr<Time> MatroskaDemuxer::seek_to_most_recent_keyframe(Track track,
     }
 
     auto& track_status = *TRY(get_track_status(track));
-    TRY(m_reader.seek_to_random_access_point(track_status.iterator, timestamp));
+    auto seeked_iterator = TRY(m_reader.seek_to_random_access_point(track_status.iterator, timestamp));
+    VERIFY(seeked_iterator.last_timestamp().has_value());
+
+    auto last_sample = earliest_available_sample;
+    if (!last_sample.has_value()) {
+        last_sample = track_status.iterator.last_timestamp();
+    }
+    if (last_sample.has_value()) {
+        bool skip_seek = seeked_iterator.last_timestamp().value() <= last_sample.value() && last_sample.value() <= timestamp;
+        dbgln_if(MATROSKA_DEBUG, "The last available sample at {}ms is {}closer to target timestamp {}ms than the keyframe at {}ms, {}", last_sample->to_milliseconds(), skip_seek ? ""sv : "not "sv, timestamp.to_milliseconds(), seeked_iterator.last_timestamp()->to_milliseconds(), skip_seek ? "skipping seek"sv : "seeking"sv);
+        if (skip_seek) {
+            return OptionalNone();
+        }
+    }
+
+    track_status.iterator = move(seeked_iterator);
     return track_status.iterator.last_timestamp();
 }
 
diff --git a/Userland/Libraries/LibVideo/Containers/Matroska/MatroskaDemuxer.h b/Userland/Libraries/LibVideo/Containers/Matroska/MatroskaDemuxer.h
index bb55a8911d..660175ca2c 100644
--- a/Userland/Libraries/LibVideo/Containers/Matroska/MatroskaDemuxer.h
+++ b/Userland/Libraries/LibVideo/Containers/Matroska/MatroskaDemuxer.h
@@ -27,7 +27,7 @@ public:
 
     DecoderErrorOr<Vector<Track>> get_tracks_for_type(TrackType type) override;
 
-    DecoderErrorOr<Time> seek_to_most_recent_keyframe(Track track, Time timestamp) override;
+    DecoderErrorOr<Optional<Time>> seek_to_most_recent_keyframe(Track track, Time timestamp, Optional<Time> earliest_available_sample = OptionalNone()) override;
 
     DecoderErrorOr<Time> duration() override;
 
diff --git a/Userland/Libraries/LibVideo/Containers/Matroska/Reader.cpp b/Userland/Libraries/LibVideo/Containers/Matroska/Reader.cpp
index 62d9daaf94..b634c3bae9 100644
--- a/Userland/Libraries/LibVideo/Containers/Matroska/Reader.cpp
+++ b/Userland/Libraries/LibVideo/Containers/Matroska/Reader.cpp
@@ -806,7 +806,7 @@ DecoderErrorOr<void> Reader::seek_to_cue_for_timestamp(SampleIterator& iterator,
     return {};
 }
 
-static DecoderErrorOr<bool> find_keyframe_before_timestamp(SampleIterator& iterator, Time const& timestamp)
+static DecoderErrorOr<void> search_clusters_for_keyframe_before_timestamp(SampleIterator& iterator, Time const& timestamp)
 {
 #if MATROSKA_DEBUG
     size_t inter_frames_count;
@@ -837,10 +837,9 @@ static DecoderErrorOr<bool> find_keyframe_before_timestamp(SampleIterator& itera
         dbgln("Seeked to a keyframe with {} inter frames to skip", inter_frames_count);
 #endif
         iterator = last_keyframe.release_value();
-        return true;
     }
 
-    return false;
+    return {};
 }
 
 DecoderErrorOr<bool> Reader::has_cues_for_track(u64 track_number)
@@ -849,37 +848,23 @@ DecoderErrorOr<bool> Reader::has_cues_for_track(u64 track_number)
     return m_cues.contains(track_number);
 }
 
-DecoderErrorOr<void> Reader::seek_to_random_access_point(SampleIterator& iterator, Time timestamp)
+DecoderErrorOr<SampleIterator> Reader::seek_to_random_access_point(SampleIterator iterator, Time timestamp)
 {
-    if (iterator.m_last_timestamp == timestamp)
-        return {};
-
     if (TRY(has_cues_for_track(iterator.m_track.track_number()))) {
-        auto seeked_iterator = iterator;
-        TRY(seek_to_cue_for_timestamp(seeked_iterator, timestamp));
-        VERIFY(seeked_iterator.m_last_timestamp <= timestamp);
-
-        // We only need to seek to a keyframe if it's not faster to continue from the current position.
-        if (timestamp < iterator.m_last_timestamp || seeked_iterator.m_last_timestamp > iterator.m_last_timestamp)
-            iterator = seeked_iterator;
-        return {};
+        TRY(seek_to_cue_for_timestamp(iterator, timestamp));
+        VERIFY(iterator.last_timestamp().has_value() && iterator.last_timestamp().value() <= timestamp);
+        return iterator;
     }
 
-    // FIXME: This could cache the keyframes it finds. Is it worth doing? Probably not, most files will have Cues :^)
-    if (timestamp < iterator.last_timestamp() || iterator.last_timestamp().is_negative()) {
+    if (!iterator.last_timestamp().has_value() || timestamp < iterator.last_timestamp().value()) {
         // If the timestamp is before the iterator's current position, then we need to start from the beginning of the Segment.
         iterator = TRY(create_sample_iterator(iterator.m_track.track_number()));
-        if (!TRY(find_keyframe_before_timestamp(iterator, timestamp)))
-            return DecoderError::corrupted("No random access points found"sv);
-
-        return {};
+        TRY(search_clusters_for_keyframe_before_timestamp(iterator, timestamp));
+        return iterator;
     }
 
-    auto seeked_iterator = iterator;
-    if (TRY(find_keyframe_before_timestamp(seeked_iterator, timestamp)))
-        iterator = seeked_iterator;
-    VERIFY(iterator.last_timestamp() <= timestamp);
-    return {};
+    TRY(search_clusters_for_keyframe_before_timestamp(iterator, timestamp));
+    return iterator;
 }
 
 DecoderErrorOr<Optional<Vector<CuePoint> const&>> Reader::cue_points_for_track(u64 track_number)
diff --git a/Userland/Libraries/LibVideo/Containers/Matroska/Reader.h b/Userland/Libraries/LibVideo/Containers/Matroska/Reader.h
index 5df0912d37..8ee14ec951 100644
--- a/Userland/Libraries/LibVideo/Containers/Matroska/Reader.h
+++ b/Userland/Libraries/LibVideo/Containers/Matroska/Reader.h
@@ -38,7 +38,7 @@ public:
     DecoderErrorOr<size_t> track_count();
 
     DecoderErrorOr<SampleIterator> create_sample_iterator(u64 track_number);
-    DecoderErrorOr<void> seek_to_random_access_point(SampleIterator&, Time);
+    DecoderErrorOr<SampleIterator> seek_to_random_access_point(SampleIterator, Time);
     DecoderErrorOr<Optional<Vector<CuePoint> const&>> cue_points_for_track(u64 track_number);
     DecoderErrorOr<bool> has_cues_for_track(u64 track_number);
 
@@ -83,7 +83,7 @@ class SampleIterator {
 public:
     DecoderErrorOr<Block> next_block();
     Cluster const& current_cluster() { return *m_current_cluster; }
-    Time const& last_timestamp() { return m_last_timestamp; }
+    Optional<Time> const& last_timestamp() { return m_last_timestamp; }
 
 private:
     friend class Reader;
@@ -107,7 +107,7 @@ private:
     // Must always point to an element ID or the end of the stream.
     size_t m_position { 0 };
 
-    Time m_last_timestamp { Time::min() };
+    Optional<Time> m_last_timestamp;
 
     Optional<Cluster> m_current_cluster;
 };
diff --git a/Userland/Libraries/LibVideo/PlaybackManager.cpp b/Userland/Libraries/LibVideo/PlaybackManager.cpp
index 84bfddf81d..9a808402b8 100644
--- a/Userland/Libraries/LibVideo/PlaybackManager.cpp
+++ b/Userland/Libraries/LibVideo/PlaybackManager.cpp
@@ -114,11 +114,11 @@ void PlaybackManager::seek_to_timestamp(Time target_timestamp)
     TRY_OR_FATAL_ERROR(m_playback_handler->seek(target_timestamp, m_seek_mode));
 }
 
-Time PlaybackManager::seek_demuxer_to_most_recent_keyframe(Time timestamp)
+Optional<Time> PlaybackManager::seek_demuxer_to_most_recent_keyframe(Time timestamp, Optional<Time> earliest_available_sample)
 {
     // FIXME: When the demuxer is getting samples off the main thread in the future, this needs to
     //        mutex so that seeking can't happen while that thread is getting a sample.
-    auto result = m_demuxer->seek_to_most_recent_keyframe(m_selected_video_track, timestamp);
+    auto result = m_demuxer->seek_to_most_recent_keyframe(m_selected_video_track, timestamp, move(earliest_available_sample));
     if (result.is_error())
         on_decoder_error(result.release_error());
     return result.release_value();
@@ -459,18 +459,30 @@ private:
 
     ErrorOr<void> on_enter() override
     {
-        auto keyframe_timestamp = manager().seek_demuxer_to_most_recent_keyframe(m_target_timestamp);
-        dbgln_if(PLAYBACK_MANAGER_DEBUG, "{} seeking to timestamp target {}ms, selected keyframe at {}ms", m_seek_mode == SeekMode::Accurate ? "Accurate"sv : "Fast"sv, m_target_timestamp.to_milliseconds(), keyframe_timestamp.to_milliseconds());
+        auto earliest_available_sample = manager().m_last_present_in_media_time;
+        if (manager().m_next_frame.has_value() && manager().m_next_frame->is_frame()) {
+            earliest_available_sample = min(earliest_available_sample, manager().m_next_frame->timestamp());
+        }
+        auto keyframe_timestamp = manager().seek_demuxer_to_most_recent_keyframe(m_target_timestamp, earliest_available_sample);
+
+#if PLAYBACK_MANAGER_DEBUG
+        auto seek_mode_name = m_seek_mode == SeekMode::Accurate ? "Accurate"sv : "Fast"sv;
+        if (keyframe_timestamp.has_value()) {
+            dbgln("{} seeking to timestamp target {}ms, selected keyframe at {}ms", seek_mode_name, m_target_timestamp.to_milliseconds(), keyframe_timestamp->to_milliseconds());
+        } else {
+            dbgln("{} seeking to timestamp target {}ms, demuxer kept its iterator position", seek_mode_name, m_target_timestamp.to_milliseconds());
+        }
+#endif
 
         if (m_seek_mode == SeekMode::Fast) {
-            m_target_timestamp = keyframe_timestamp;
+            m_target_timestamp = keyframe_timestamp.value_or(earliest_available_sample);
         }
 
-        if (m_target_timestamp < manager().m_last_present_in_media_time) {
+        if (keyframe_timestamp.has_value()) {
             dbgln_if(PLAYBACK_MANAGER_DEBUG, "Timestamp is earlier than current media time, clearing queue");
             manager().m_frame_queue->clear();
             manager().m_next_frame.clear();
-        } else if (manager().m_next_frame.has_value() && manager().m_next_frame.value().timestamp() > m_target_timestamp) {
+        } else if (m_target_timestamp >= manager().m_last_present_in_media_time && manager().m_next_frame.has_value() && manager().m_next_frame.value().timestamp() > m_target_timestamp) {
             manager().m_last_present_in_media_time = m_target_timestamp;
             return exit_seek();
         }
@@ -571,7 +583,11 @@ private:
 
     ErrorOr<void> play() override
     {
-        manager().m_last_present_in_media_time = manager().seek_demuxer_to_most_recent_keyframe(Time::zero());
+        manager().m_next_frame.clear();
+        manager().m_frame_queue->clear();
+        auto start_timestamp = manager().seek_demuxer_to_most_recent_keyframe(Time::zero());
+        VERIFY(start_timestamp.has_value());
+        manager().m_last_present_in_media_time = start_timestamp.release_value();
         return replace_handler_and_delete_this<PlayingStateHandler>();
     }
     bool is_playing() override { return false; };
diff --git a/Userland/Libraries/LibVideo/PlaybackManager.h b/Userland/Libraries/LibVideo/PlaybackManager.h
index 2006fa6121..3a92b2453d 100644
--- a/Userland/Libraries/LibVideo/PlaybackManager.h
+++ b/Userland/Libraries/LibVideo/PlaybackManager.h
@@ -126,7 +126,7 @@ private:
 
     void start_timer(int milliseconds);
     void timer_callback();
-    Time seek_demuxer_to_most_recent_keyframe(Time timestamp);
+    Optional<Time> seek_demuxer_to_most_recent_keyframe(Time timestamp, Optional<Time> earliest_available_sample = OptionalNone());
 
     bool decode_and_queue_one_sample();
     void on_decode_timer();