diff --git a/db/compaction_job.cc b/db/compaction_job.cc
index 0e2f68f21..f345e1f96 100644
--- a/db/compaction_job.cc
+++ b/db/compaction_job.cc
@@ -747,6 +747,14 @@ void CompactionJob::ProcessKeyValueCompaction(SubcompactionState* sub_compact) {
       shutting_down_));
   auto c_iter = sub_compact->c_iter.get();
   c_iter->SeekToFirst();
+  if (c_iter->Valid() &&
+      sub_compact->compaction->output_level() != 0) {
+    // ShouldStopBefore() maintains state based on keys processed so far. The
+    // compaction loop always calls it on the "next" key, thus won't tell it the
+    // first key. So we do that here.
+    sub_compact->ShouldStopBefore(
+      c_iter->key(), sub_compact->current_output_file_size);
+  }
   const auto& c_iter_stats = c_iter->iter_stats();
   auto sample_begin_offset_iter = sample_begin_offsets.cbegin();
   // data_begin_offset and compression_dict are only valid while generating
@@ -766,21 +774,7 @@ void CompactionJob::ProcessKeyValueCompaction(SubcompactionState* sub_compact) {
     if (end != nullptr &&
         cfd->user_comparator()->Compare(c_iter->user_key(), *end) >= 0) {
       break;
-    } else if (sub_compact->compaction->output_level() != 0 &&
-               sub_compact->ShouldStopBefore(
-                   key, sub_compact->current_output_file_size) &&
-               sub_compact->builder != nullptr) {
-      CompactionIterationStats range_del_out_stats;
-      status = FinishCompactionOutputFile(input->status(), sub_compact,
-                                          range_del_agg.get(),
-                                          &range_del_out_stats, &key);
-      RecordDroppedKeys(range_del_out_stats,
-                        &sub_compact->compaction_job_stats);
-      if (!status.ok()) {
-        break;
-      }
     }
-
     if (c_iter_stats.num_input_records % kRecordStatsEvery ==
         kRecordStatsEvery - 1) {
       RecordDroppedKeys(c_iter_stats, &sub_compact->compaction_job_stats);
@@ -852,17 +846,37 @@ void CompactionJob::ProcessKeyValueCompaction(SubcompactionState* sub_compact) {
       }
     }
 
-    // Close output file if it is big enough
+    // Close output file if it is big enough. Two possibilities determine it's
+    // time to close it: (1) the current key should be this file's last key, (2)
+    // the next key should not be in this file.
+    //
     // TODO(aekmekji): determine if file should be closed earlier than this
     // during subcompactions (i.e. if output size, estimated by input size, is
     // going to be 1.2MB and max_output_file_size = 1MB, prefer to have 0.6MB
     // and 0.6MB instead of 1MB and 0.2MB)
+    bool output_file_ended = false;
+    Status input_status;
     if (sub_compact->compaction->output_level() != 0 &&
         sub_compact->current_output_file_size >=
             sub_compact->compaction->max_output_file_size()) {
-      Status input_status = input->status();
-      c_iter->Next();
-
+      // (1) this key terminates the file. For historical reasons, the iterator
+      // status before advancing will be given to FinishCompactionOutputFile().
+      input_status = input->status();
+      output_file_ended = true;
+    }
+    c_iter->Next();
+    if (!output_file_ended && c_iter->Valid() &&
+        sub_compact->compaction->output_level() != 0 &&
+        sub_compact->ShouldStopBefore(
+          c_iter->key(), sub_compact->current_output_file_size) &&
+        sub_compact->builder != nullptr) {
+      // (2) this key belongs to the next file. For historical reasons, the
+      // iterator status after advancing will be given to
+      // FinishCompactionOutputFile().
+      input_status = input->status();
+      output_file_ended = true;
+    }
+    if (output_file_ended) {
       const Slice* next_key = nullptr;
       if (c_iter->Valid()) {
         next_key = &c_iter->key();
@@ -878,8 +892,6 @@ void CompactionJob::ProcessKeyValueCompaction(SubcompactionState* sub_compact) {
         // files.
         sub_compact->compression_dict = std::move(compression_dict);
       }
-    } else {
-      c_iter->Next();
     }
   }