diff --git a/packager/media/formats/webvtt/webvtt_pipeline_unittest.cc b/packager/media/formats/webvtt/webvtt_pipeline_unittest.cc
index 3423e7ae43..565858891c 100644
--- a/packager/media/formats/webvtt/webvtt_pipeline_unittest.cc
+++ b/packager/media/formats/webvtt/webvtt_pipeline_unittest.cc
@@ -26,6 +26,7 @@ TEST(WebVttTextPipelineTest, SegmentedOutput) {
   const char* kOutput1 = "memory://output/template-1.vtt";
   const char* kOutput2 = "memory://output/template-2.vtt";
   const char* kOutput3 = "memory://output/template-3.vtt";
+  const char* kOutput4 = "memory://output/template-4.vtt";
 
   const char* kInputFile = "memory://input.vtt";
   const char* kInput =
@@ -53,8 +54,14 @@ TEST(WebVttTextPipelineTest, SegmentedOutput) {
       "Thank you.\n";
 
   // Segment One
-  // 00:00:10.000 to 00:00:20.000
+  // 00:00:00.000 to 00:00:10.000
   const char* kExpectedOutput1 =
+      "WEBVTT\n"
+      "\n";
+
+  // Segment Two
+  // 00:00:10.000 to 00:00:20.000
+  const char* kExpectedOutput2 =
       "WEBVTT\n"
       "\n"
       "1\n"
@@ -62,9 +69,9 @@ TEST(WebVttTextPipelineTest, SegmentedOutput) {
       "This blade has a dark past.\n"
       "\n";
 
-  // Segment Two
+  // Segment Three
   // 00:00:20.000 to 00:00:30.000
-  const char* kExpectedOutput2 =
+  const char* kExpectedOutput3 =
       "WEBVTT\n"
       "\n"
       "1\n"
@@ -80,9 +87,9 @@ TEST(WebVttTextPipelineTest, SegmentedOutput) {
       "You're a fool for traveling alone,\nso completely unprepared.\n"
       "\n";
 
-  // Segment Three
+  // Segment Four
   // 00:00:30.000 to 00:00:40.000
-  const char* kExpectedOutput3 =
+  const char* kExpectedOutput4 =
       "WEBVTT\n"
       "\n"
       "3\n"
@@ -128,6 +135,7 @@ TEST(WebVttTextPipelineTest, SegmentedOutput) {
   ASSERT_FILE_STREQ(kOutput1, kExpectedOutput1);
   ASSERT_FILE_STREQ(kOutput2, kExpectedOutput2);
   ASSERT_FILE_STREQ(kOutput3, kExpectedOutput3);
+  ASSERT_FILE_STREQ(kOutput4, kExpectedOutput4);
 }
 }  // namespace media
 }  // namespace shaka
diff --git a/packager/media/formats/webvtt/webvtt_segmenter.cc b/packager/media/formats/webvtt/webvtt_segmenter.cc
index c1bbca89bc..d122599fa3 100644
--- a/packager/media/formats/webvtt/webvtt_segmenter.cc
+++ b/packager/media/formats/webvtt/webvtt_segmenter.cc
@@ -35,7 +35,10 @@ Status WebVttSegmenter::Process(std::unique_ptr<StreamData> stream_data) {
 Status WebVttSegmenter::OnFlushRequest(size_t input_stream_index) {
   Status status;
   while (status.ok() && samples_.size()) {
-    status.Update(OnSegmentEnd());
+    // It is not possible for there to be any gaps, or else we would have
+    // already ended the segments before them. So just close the last remaining
+    // open segments.
+    OnSegmentEnd(samples_.top().segment);
   }
   return status.ok() ? FlushAllDownstreams() : status;
 }
@@ -68,23 +71,19 @@ Status WebVttSegmenter::OnTextSample(std::shared_ptr<const TextSample> sample) {
     samples_.push(seg_sample);
   }
 
-  Status status;
-
-  while (status.ok() && samples_.size() &&
-         samples_.top().segment < start_segment) {
-    // WriteNextSegment will pop elements from |samples_| which will
-    // eventually allow the loop to exit.
-    status.Update(OnSegmentEnd());
+  // Output all the segments that come before the start of this cue's first
+  // segment.
+  for (; current_segment_ < start_segment; current_segment_++) {
+    Status status = OnSegmentEnd(current_segment_);
+    if (!status.ok()) {
+      return status;
+    }
   }
 
-  return status;
+  return Status::OK;
 }
 
-Status WebVttSegmenter::OnSegmentEnd() {
-  DCHECK(samples_.size());
-
-  const uint64_t segment = samples_.top().segment;
-
+Status WebVttSegmenter::OnSegmentEnd(uint64_t segment) {
   Status status;
   while (status.ok() && samples_.size() && samples_.top().segment == segment) {
     status.Update(
diff --git a/packager/media/formats/webvtt/webvtt_segmenter.h b/packager/media/formats/webvtt/webvtt_segmenter.h
index 743215493d..d3d19a78cc 100644
--- a/packager/media/formats/webvtt/webvtt_segmenter.h
+++ b/packager/media/formats/webvtt/webvtt_segmenter.h
@@ -56,8 +56,10 @@ class WebVttSegmenter : public MediaHandler {
   Status InitializeInternal() override;
 
   Status OnTextSample(std::shared_ptr<const TextSample> sample);
-  Status OnSegmentEnd();
 
+  Status OnSegmentEnd(uint64_t segment);
+
+  uint64_t current_segment_ = 0;
   uint64_t segment_duration_ms_;
   std::priority_queue<WebVttSegmentedTextSample,
                       std::vector<WebVttSegmentedTextSample>,
diff --git a/packager/media/formats/webvtt/webvtt_segmenter_unittest.cc b/packager/media/formats/webvtt/webvtt_segmenter_unittest.cc
index d56933a89d..5197d872ae 100644
--- a/packager/media/formats/webvtt/webvtt_segmenter_unittest.cc
+++ b/packager/media/formats/webvtt/webvtt_segmenter_unittest.cc
@@ -142,7 +142,7 @@ TEST_F(WebVttSegmenterTest, CreatesSegmentsForCues) {
 //           |          |
 //           |          | [---B---]
 //           |          |
-TEST_F(WebVttSegmenterTest, SkipsEmptySegments) {
+TEST_F(WebVttSegmenterTest, DoesntSkipsEmptySegments) {
   const uint64_t kSampleDuration = kSegmentDuration / 2;
 
   {
@@ -160,7 +160,11 @@ TEST_F(WebVttSegmenterTest, SkipsEmptySegments) {
         OnProcess(IsSegmentInfo(kStreamIndex, kStartTimeSigned,
                                 kSegmentDuration, !kSubSegment, !kEncrypted)));
 
-    // There is no segment two
+    // Segment two (empty)
+    EXPECT_CALL(*Output(kOutputIndex),
+                OnProcess(IsSegmentInfo(
+                    kStreamIndex, kStartTimeSigned + kSegmentDuration,
+                    kSegmentDuration, !kSubSegment, !kEncrypted)));
 
     // Segment Three
     EXPECT_CALL(*Output(kOutputIndex),