diff --git a/plugins/eddn.py b/plugins/eddn.py
index 9bfab900..39ecf147 100644
--- a/plugins/eddn.py
+++ b/plugins/eddn.py
@@ -223,22 +223,24 @@ class EDDNSender:
 
     def convert_legacy_file(self):
         """Convert a legacy file's contents into the sqlite3 db."""
+        # DEPRECATED: Legacy files no longer used as of 5.6.0. Will remove in 6.0 or later.
         filename = config.app_dir_path / 'replay.jsonl'
+        if not filename.exists():
+            return
+        logger.info("Converting legacy `replay.jsonl` to `eddn_queue-v1.db`")
         try:
-            with open(filename, 'r+', buffering=1) as replay_file:
-                logger.info("Converting legacy `replay.jsonl` to `eddn_queue-v1.db`")
+            with filename.open('r', encoding='utf-8') as replay_file:
                 for line in replay_file:
                     cmdr, msg = json.loads(line)
                     self.add_message(cmdr, msg)
-
-        except FileNotFoundError:
+        except Exception as e:
+            logger.exception("Failed to convert legacy file: %s", e)
             return
-
-        logger.info("Conversion to `eddn_queue-v1.db` complete, removing `replay.jsonl`")
-        # Best effort at removing the file/contents
-        with open(filename, 'w') as replay_file:
-            replay_file.truncate()
-        os.unlink(filename)
+        logger.info("Conversion complete, removing `replay.jsonl`")
+        try:
+            filename.unlink()
+        except Exception as e:
+            logger.warning("Could not delete legacy file: %s", e)
 
     def close(self) -> None:
         """Clean up any resources."""