diff --git a/db/db_test2.cc b/db/db_test2.cc
index 368ebe936..6b0ee157e 100644
--- a/db/db_test2.cc
+++ b/db/db_test2.cc
@@ -4177,6 +4177,39 @@ TEST_F(DBTest2, CrashInRecoveryMultipleCF) {
                                           options));
   }
 }
+
+TEST_F(DBTest2, SeekFileRangeDeleteTail) {
+  Options options = CurrentOptions();
+  options.prefix_extractor.reset(NewCappedPrefixTransform(1));
+  options.num_levels = 3;
+  DestroyAndReopen(options);
+
+  ASSERT_OK(Put("a", "a"));
+  const Snapshot* s1 = db_->GetSnapshot();
+  ASSERT_OK(
+      db_->DeleteRange(WriteOptions(), db_->DefaultColumnFamily(), "a", "f"));
+  ASSERT_OK(Put("b", "a"));
+  ASSERT_OK(Flush());
+
+  ASSERT_OK(Put("x", "a"));
+  ASSERT_OK(Put("z", "a"));
+  ASSERT_OK(Flush());
+
+  CompactRangeOptions cro;
+  cro.change_level = true;
+  cro.target_level = 2;
+  ASSERT_OK(db_->CompactRange(cro, nullptr, nullptr));
+
+  {
+    ReadOptions ro;
+    ro.total_order_seek = true;
+    std::unique_ptr<Iterator> iter(db_->NewIterator(ro));
+    iter->Seek("e");
+    ASSERT_TRUE(iter->Valid());
+    ASSERT_EQ("x", iter->key().ToString());
+  }
+  db_->ReleaseSnapshot(s1);
+}
 }  // namespace rocksdb
 
 #ifdef ROCKSDB_UNITTESTS_WITH_CUSTOM_OBJECTS_FROM_STATIC_LIBS
diff --git a/db/version_set.cc b/db/version_set.cc
index a73806b81..ca6c6fb10 100644
--- a/db/version_set.cc
+++ b/db/version_set.cc
@@ -867,7 +867,8 @@ class LevelIterator final : public InternalIterator {
         icomparator_(icomparator),
         user_comparator_(icomparator.user_comparator()),
         flevel_(flevel),
-        prefix_extractor_(prefix_extractor),
+        prefix_extractor_(read_options.total_order_seek ? nullptr
+                                                        : prefix_extractor),
         file_read_hist_(file_read_hist),
         should_sample_(should_sample),
         caller_(caller),