diff --git a/plugins/eddn.py b/plugins/eddn.py
index 693f01fc..1401b0c8 100644
--- a/plugins/eddn.py
+++ b/plugins/eddn.py
@@ -255,6 +255,9 @@ Msg:\n{msg}'''
                 if not len(self.replaylog) % self.REPLAYFLUSH:
                     self.flush()
 
+            except requests.exceptions.HTTPError as e:
+                status['text'] = self.http_error_to_log(e)
+
             except requests.exceptions.RequestException as e:
                 logger.debug('Failed sending', exc_info=e)
                 status['text'] = _("Error: Can't connect to EDDN")
@@ -267,6 +270,24 @@ Msg:\n{msg}'''
 
         self.parent.after(self.REPLAYPERIOD, self.sendreplay)
 
+    @staticmethod
+    def http_error_to_log(exception: requests.exceptions.HTTPError) -> str:
+        """Convert an exception from raise_for_status to a log message and displayed error."""
+        status_code = exception.errno
+
+        if status_code == 429:  # HTTP UPGRADE REQUIRED
+            logger.warning('EDMC is sending schemas that are too old')
+            return _("EDDN Error: EDMC is too old for EDDN. Please update.")
+
+        elif status_code == 400:
+            # we a validation check or something else.
+            logger.warning(f'EDDN Error: {status_code} -- {exception.response}')
+            return _("EDDN Error: Validation Failed (EDMC Too Old?). See Log")
+
+        else:
+            logger.warning(f'Unknown status code from EDDN: {status_code} -- {exception.response}')
+            return _("EDDN Error: Returned {STATUS} status code").format(status_code)
+
     def export_commodities(self, data: Mapping[str, Any], is_beta: bool, is_odyssey: bool) -> None:  # noqa: CCR001
         """
         Update EDDN with the commodities on the current (lastStarport) station.