diff --git a/executor/executor/executor.py b/executor/executor/executor.py
index 5890ee26..36a14aa7 100644
--- a/executor/executor/executor.py
+++ b/executor/executor/executor.py
@@ -458,7 +458,8 @@ def orchestrate_earthmover(self):
         # if we're here, the first pass of Earthmover was successful
         if (self.send_to_ods                          # i.e. we've only tried matching this year's students so far
             and self.cross_year_match_available       # and we have access to EDU
-            and self.num_unmatched_students > 0       # and there are unmatched students from the first pass
+            and (self.num_unmatched_students is None  # and either there were no matches at all
+                 or self.num_unmatched_students > 0)  # or there are any remaining unmatched students
         ):
             # then take a second pass with the cross-year roster from EDU
             # and thus produce a second output set to be sideloaded
@@ -539,10 +540,13 @@ def cross_year_pass(self, primary):
         self.upload_artifact(artifact.CROSS_YEAR_ROSTER)
         os.environ["EDFI_ROSTER_FILE"] = os.path.abspath(config.CROSS_YEAR_ROSTER_PATH)
 
+        # Boolean to capture whether our first run met the match rate threshold
+        met_initial_threshold = self.highest_match_rate >= config.REQUIRED_ID_MATCH_RATE
+
         # If we hit the required match rate on the first pass, constrain to the ID column that won.
         # Otherwise, we run again and check against all ID types.
         # The bundle always appends studentUniqueId internally, so we pass an empty list when that's what won.
-        if self.highest_match_rate >= config.REQUIRED_ID_MATCH_RATE:
+        if met_initial_threshold:
 
             # use only the students who failed to match the primary ID from the first run
             unmatched_path = os.path.join(first_run_output_dir, os.path.basename(artifact.UNMATCHED_STUDENTS.path))
@@ -566,10 +570,11 @@ def cross_year_pass(self, primary):
         self.earthmover_run(artifact.EM_RESULTS_X_YEAR.path)
         artifact.EM_RESULTS_X_YEAR.needs_upload = True
         self.upload_artifact(artifact.EM_RESULTS_X_YEAR)
-        # Record our new second pass match rate.
-        # If we don't meet the threshold, halt!
-        self.record_highest_match_rate()
-        self.enforce_match_threshold()
+        
+        if not met_initial_threshold:
+            # Only enforce our match threshold if the initial run did not hit
+            self.record_highest_match_rate()
+            self.enforce_match_threshold()
 
         self.logger.info(f"cross-year pass: match_rates: {load_match_rates()}")
         count = count_unmatched_students()