diff --git a/app/widget/timelinewidget/timelineundo.h b/app/widget/timelinewidget/timelineundo.h
index 8c472a658..3e38eb34d 100644
--- a/app/widget/timelinewidget/timelineundo.h
+++ b/app/widget/timelinewidget/timelineundo.h
@@ -463,7 +463,6 @@ public:
         Q_ASSERT(i == 0 || time > times_.at(i-1));
 
         QVector<Block*> splits(blocks_.size());
-        commands_.resize(blocks_.size());
 
         for (int j=0;j<blocks_.size();j++) {
           Block* b = blocks_.at(j);
@@ -472,7 +471,7 @@ public:
             BlockSplitCommand* split_command = new BlockSplitCommand(b, time);
             split_command->redo();
             splits.replace(j, split_command->new_block());
-            commands_.replace(j, split_command);
+            commands_.append(split_command);
           } else {
             splits.replace(j, nullptr);
           }
@@ -2045,8 +2044,8 @@ public:
     }
 
     foreach (auto add_gap, gaps_added_) {
-      add_gap.gap->setParent(add_gap.before->parent());
-      add_gap.before->track()->InsertBlockAfter(add_gap.gap, add_gap.before);
+      add_gap.gap->setParent(add_gap.track->parent());
+      add_gap.track->InsertBlockAfter(add_gap.gap, add_gap.before);
     }
 
     foreach (Track* track, working_tracks_) {
@@ -2121,6 +2120,7 @@ private:
 
     QVector<Block*> blocks_to_split;
     QVector<Block*> blocks_to_append_gap_to;
+    QVector<Track*> tracks_to_append_gap_to;
 
     foreach (Track* track, working_tracks_) {
       foreach (Block* b, track->Blocks()) {
@@ -2129,11 +2129,24 @@ private:
           gaps_to_extend_.append(b);
           break;
         } else if (dynamic_cast<ClipBlock*>(b) && b->out() >= point_) {
-          if (b->out() > point_) {
+          bool append_gap = true;
+
+          if (b->in() == point_) {
+            // The only reason we should be here is if this block is at the start of the track,
+            // in which case no split needs to occur
+            b = nullptr;
+          } else if (b->out() > point_) {
+            // Block must be split as well as having a gap appended to it
             blocks_to_split.append(b);
+          } else if (!b->next()) {
+            // At the end of a track, no gap needs to be added at all
+            append_gap = false;
           }
 
-          blocks_to_append_gap_to.append(b);
+          if (append_gap) {
+            tracks_to_append_gap_to.append(track);
+            blocks_to_append_gap_to.append(b);
+          }
           break;
         }
       }
@@ -2143,11 +2156,11 @@ private:
       split_command_ = new BlockSplitPreservingLinksCommand(blocks_to_split, {point_});
     }
 
-    foreach (Block* block, blocks_to_append_gap_to) {
+    for (int i=0; i<blocks_to_append_gap_to.size(); i++) {
       GapBlock* gap = new GapBlock();
       gap->set_length_and_media_out(length_);
       gap->setParent(&memory_manager_);
-      gaps_added_.append({gap, block});
+      gaps_added_.append({gap, blocks_to_append_gap_to.at(i), tracks_to_append_gap_to.at(i)});
     }
   }
 
@@ -2166,6 +2179,7 @@ private:
   struct AddGap {
     GapBlock* gap;
     Block* before;
+    Track* track;
   };
 
   QVector<AddGap> gaps_added_;
diff --git a/tests/timeline/timeline-tests.cpp b/tests/timeline/timeline-tests.cpp
index 7c68284f2..529168e30 100644
--- a/tests/timeline/timeline-tests.cpp
+++ b/tests/timeline/timeline-tests.cpp
@@ -488,4 +488,112 @@ OLIVE_ADD_TEST(ReplaceBlockWithGap_ClipsAndTransitions)
   OLIVE_TEST_END;
 }
 
+OLIVE_ADD_TEST(InsertGaps_SingleTrack)
+{
+  TIMELINE_TEST_START;
+
+  sequence.add_default_nodes();
+
+  TrackList *list = sequence.track_list(Track::kVideo);
+  Track *track = list->GetTracks().first();
+
+  ClipBlock *a = new ClipBlock();
+  a->setParent(&project);
+  track->AppendBlock(a);
+
+  ClipBlock *b = new ClipBlock();
+  b->setParent(&project);
+  track->AppendBlock(b);
+
+  ClipBlock *c = new ClipBlock();
+  c->setParent(&project);
+  track->AppendBlock(c);
+
+  OLIVE_ASSERT(track->Blocks().size() == 3);
+  OLIVE_ASSERT(track->Blocks().at(0) == a);
+  OLIVE_ASSERT(track->Blocks().at(1) == b);
+  OLIVE_ASSERT(track->Blocks().at(2) == c);
+
+  {
+    // Insert gap at the start of the track, all blocks should be unsplit and shifted to the right
+    TrackListInsertGaps command(list, 0, 2);
+    command.redo();
+
+    OLIVE_ASSERT(track->Blocks().size() == 4);
+    OLIVE_ASSERT(dynamic_cast<GapBlock *>(track->Blocks().at(0)));
+    OLIVE_ASSERT(track->Blocks().at(0)->length() == 2);
+    OLIVE_ASSERT(track->Blocks().at(1) == a);
+    OLIVE_ASSERT(track->Blocks().at(2) == b);
+    OLIVE_ASSERT(track->Blocks().at(3) == c);
+
+    command.undo();
+
+    OLIVE_ASSERT(track->Blocks().size() == 3);
+    OLIVE_ASSERT(track->Blocks().at(0) == a);
+    OLIVE_ASSERT(track->Blocks().at(1) == b);
+    OLIVE_ASSERT(track->Blocks().at(2) == c);
+  }
+
+  {
+    // Insert gap in the middle of block A, block A should be halved with a copy at 2 and the gap at 1
+    TrackListInsertGaps command(list, rational(1, 2), 2);
+    command.redo();
+
+    OLIVE_ASSERT(track->Blocks().size() == 5);
+    OLIVE_ASSERT(track->Blocks().at(0) == a);
+    OLIVE_ASSERT(track->Blocks().at(0)->length() == rational(1, 2));
+    OLIVE_ASSERT(dynamic_cast<GapBlock *>(track->Blocks().at(1)));
+    OLIVE_ASSERT(dynamic_cast<ClipBlock*>(track->Blocks().at(2)));
+    OLIVE_ASSERT(track->Blocks().at(3) == b);
+    OLIVE_ASSERT(track->Blocks().at(4) == c);
+
+    command.undo();
+
+    OLIVE_ASSERT(track->Blocks().size() == 3);
+    OLIVE_ASSERT(track->Blocks().at(0) == a);
+    OLIVE_ASSERT(track->Blocks().at(0)->length() = 1);
+    OLIVE_ASSERT(track->Blocks().at(1) == b);
+    OLIVE_ASSERT(track->Blocks().at(2) == c);
+  }
+
+  {
+    // Insert gap between block A and B, blocks should be unsplit with a gap at 1
+    TrackListInsertGaps command(list, 1, 2);
+    command.redo();
+
+    OLIVE_ASSERT(track->Blocks().size() == 4);
+    OLIVE_ASSERT(track->Blocks().at(0) == a);
+    OLIVE_ASSERT(dynamic_cast<GapBlock *>(track->Blocks().at(1)));
+    OLIVE_ASSERT(track->Blocks().at(2) == b);
+    OLIVE_ASSERT(track->Blocks().at(3) == c);
+
+    command.undo();
+
+    OLIVE_ASSERT(track->Blocks().size() == 3);
+    OLIVE_ASSERT(track->Blocks().at(0) == a);
+    OLIVE_ASSERT(track->Blocks().at(1) == b);
+    OLIVE_ASSERT(track->Blocks().at(2) == c);
+  }
+
+  {
+    // Insert gap at end, nothing should be added
+    TrackListInsertGaps command(list, 3, 2);
+    command.redo();
+
+    OLIVE_ASSERT(track->Blocks().size() == 3);
+    OLIVE_ASSERT(track->Blocks().at(0) == a);
+    OLIVE_ASSERT(track->Blocks().at(1) == b);
+    OLIVE_ASSERT(track->Blocks().at(2) == c);
+
+    command.undo();
+
+    OLIVE_ASSERT(track->Blocks().size() == 3);
+    OLIVE_ASSERT(track->Blocks().at(0) == a);
+    OLIVE_ASSERT(track->Blocks().at(1) == b);
+    OLIVE_ASSERT(track->Blocks().at(2) == c);
+  }
+
+  OLIVE_TEST_END;
+}
+
 }