diff --git a/application/PreorderBilling/PreorderBillingController.php b/application/PreorderBilling/PreorderBillingController.php
index d11104877..232ee4915 100644
--- a/application/PreorderBilling/PreorderBillingController.php
+++ b/application/PreorderBilling/PreorderBillingController.php
@@ -637,7 +637,14 @@ class PreorderBillingController extends mfBaseController {
             //var_dump($existing_bill);
             if(!$existing_bill) {
                 if($netoperator_config["billing-period"] == "quarterly" && $create_date->format("Ymd") > $latest_quarter_bill_date->format("Ymd")) {
-                    $this->log->debug(__METHOD__.": Skipping operator_usage ".$create_date->format("m/Y")." for preorder ".$preorder->id." because Billing date ".$create_date->format("Y-m-d")." is after latest_quarter_bill_date ".$latest_quarter_bill_date->format("Y-m-d"));
+                    // if this preorder was never billed before and activation date is before latest quarterly billing date, we still need to consider earlier months
+                    $any_previous_bill = PreorderBilling::getFirst(["product_id" => $product->id, "preorder_id" => $preorder->id]);
+                    if(!$any_previous_bill && $status_change_date->format("Ym") < $latest_quarter_bill_date->format("Ym")) {
+                        $create_date->modify("-1 months");
+                        continue;
+                    }
+                    // otherwise if activation was this month, then we need not bill anything now
+                    $this->log->debug(__METHOD__.": Skipping operator_usage blubb ".$create_date->format("m/Y")." for preorder ".$preorder->id." because Billing date ".$create_date->format("Y-m-d")." is after latest_quarter_bill_date ".$latest_quarter_bill_date->format("Y-m-d")." (status 500 change date: ".$status_change_date->format("Y-m-d").")");
                     return true;
                 }
                 $new_create_date = clone $create_date;