Reconcile up-front charges when a class switches to monthly billing

A student who enrols while a group class is pay-now is charged once at
enrolment, and that charge carries no period_key. When the class is
later switched to monthly, the daily scan — which dedups scheduled
charges by period_key — does not see the up-front charge and bills the
enrolment again for the current month, double-charging students who
had already paid. The differing payer between the two rows (student vs
guardian) was a side effect of guardian links created between the two
charge dates, not the cause.

Switching a group class into monthly now adopts each active enrolment's
up-front charge into the current month (stamping period_key and
due_date) so the scan treats that month as billed and charges from the
next month on. Enrolments with no up-front charge, or already billed
for the month, are left alone; weekly and non-group offerings are not
touched. Wired into both offering-update paths (admin form and REST).

Co-authored-by: anthropic/claude-opus-4-8

CHANGELOG.md

@@ -15,6 +15,7 @@ each change under the current top section as you work.
 
 ### Fixed
 - **A student is no longer emailed the same "Payment due" notice twice.** The daily billing scan runs whenever the site gets traffic, and on a busy day two copies of it could end up running at the same time. Neither knew about the other, so each would send its own notice for the same charge — one payment on the books, but the family saw two identical requests to pay and reasonably read it as being billed twice. Each payment is now stamped the moment its notice goes out, and a second run that reaches the same payment sees the stamp and stays quiet, so exactly one notice is sent no matter how the scan is triggered. Payments already noticed before this update are marked as such on upgrade, so nobody gets a fresh round of reminders for charges they were already told about.
+- **Switching a group class to monthly billing no longer charges students who already paid up front a second time.** When a class was set up to be paid once at sign-up and later changed to bill monthly, the daily scan did not recognise the payment already taken at enrolment — it carried no billing month — and raised a fresh charge for the current month on top of it. Families who had already paid were billed again, sometimes for a month they had covered. Changing a class to monthly now marks each enrolled student's up-front payment as covering the current month, so the scan bills them from the following month on and never doubles up on the month already paid. (Enrolments made after the switch, and classes that were always monthly, were never affected.)
 
 ## [1.5.7]
 

src/AdminMenu.php

@@ -25,6 +25,7 @@ use Unsupervised\Schedular\GroupClass\EnrollmentRepository;
 use Unsupervised\Schedular\GroupClass\GroupAccessRepository;
 use Unsupervised\Schedular\GroupClass\GroupClassController;
 use Unsupervised\Schedular\GroupClass\SessionSchedule;
+use Unsupervised\Schedular\Offering\BillingModeReconciler;
 use Unsupervised\Schedular\Offering\ClassSlotReconciler;
 use Unsupervised\Schedular\Offering\OfferingController;
 use Unsupervised\Schedular\Offering\OfferingRepository;
@@ -70,7 +71,7 @@ class AdminMenu {
 	private PaymentController $paymentController;
 	private PaymentReportController $paymentReportController;
 
-	public function __construct( AvailabilityRepository $availability, BookingRepository $bookings, OfferingRepository $offerings, QuestionRepository $questions, AnswerRepository $answers, PolicyRepository $policies, PolicyVersionRepository $policyVersions, PolicyService $policyService, AcceptanceRepository $acceptances, InviteRepository $invites, EnrollmentRepository $enrollments, GroupAccessRepository $groupAccess, StudioSettings $settings, PaymentRepository $payments, PaymentService $paymentService, BillingMethodResolver $resolver, RegistrationMailer $registrationMailer, CreditRepository $credits, GuardianService $guardians, LessonBooker $booker, RegistrationGate $gate ) {
+	public function __construct( AvailabilityRepository $availability, BookingRepository $bookings, OfferingRepository $offerings, QuestionRepository $questions, AnswerRepository $answers, PolicyRepository $policies, PolicyVersionRepository $policyVersions, PolicyService $policyService, AcceptanceRepository $acceptances, InviteRepository $invites, EnrollmentRepository $enrollments, GroupAccessRepository $groupAccess, StudioSettings $settings, PaymentRepository $payments, PaymentService $paymentService, BillingMethodResolver $resolver, RegistrationMailer $registrationMailer, CreditRepository $credits, GuardianService $guardians, LessonBooker $booker, RegistrationGate $gate, BillingModeReconciler $billingModeReconciler ) {
 		// One audit presenter and one recorder, shared by the lesson and enrolment
 		// detail views: intake is the same thing whichever registration it hangs off.
 		$intakeAudit     = new IntakeAudit( $answers, $questions, $acceptances, $policies, $policyVersions );
@@ -78,7 +79,7 @@ class AdminMenu {
 
 		$this->availabilityController         = new AvailabilityController( $availability, $offerings, new WindowValidator( $offerings ) );
 		$this->lessonController               = new LessonController( $bookings, $payments, $availability, $offerings, $intakeAudit, new AdminBooking( $availability, $offerings, $booker ), $intakeRecording );
-		$this->offeringController             = new OfferingController( $offerings, new ClassSlotReconciler( $availability ) );
+		$this->offeringController             = new OfferingController( $offerings, new ClassSlotReconciler( $availability ), $billingModeReconciler );
 		$this->questionController             = new QuestionController( $questions, $offerings );
 		$this->policyController               = new PolicyController( $policies, $policyVersions, $policyService );
 		$this->registrationController         = new RegistrationController( $invites );

src/GroupClass/EnrollmentRepository.php

@@ -82,6 +82,24 @@ class EnrollmentRepository {
 		return $count > 0;
 	}
 
+	/**
+	 * Active enrolments in one offering, oldest first.
+	 *
+	 * @return list<Enrollment>
+	 */
+	public function findActiveByOffering( int $offeringId ): array {
+		$rows = $this->db->get_results(
+			$this->db->prepare(
+				'SELECT * FROM %i WHERE offering_id = %d AND status = %s ORDER BY id ASC',
+				$this->table,
+				$offeringId,
+				Enrollment::STATUS_ACTIVE
+			)
+		);
+
+		return array_map( Enrollment::fromRow( ... ), $rows ?? [] );
+	}
+
 	/**
 	 * A student's enrolments, newest first.
 	 *

src/Offering/BillingModeReconciler.php

@@ -0,0 +1,85 @@
+<?php
+declare(strict_types=1);
+
+namespace Unsupervised\Schedular\Offering;
+
+use Unsupervised\Schedular\GroupClass\EnrollmentRepository;
+use Unsupervised\Schedular\Payment\Payment;
+use Unsupervised\Schedular\Payment\PaymentRepository;
+use Unsupervised\Schedular\Val;
+
+/**
+ * Keeps existing enrolments from being billed twice when a group class is
+ * switched from a pay-now billing mode (one-time / full-term) to a scheduled one
+ * (weekly / monthly).
+ *
+ * A student who enrols while a class is pay-now is charged once at enrolment, and
+ * that charge carries no `period_key`. The daily scan dedups scheduled charges by
+ * `period_key`, so once the class becomes scheduled the scan does not see the
+ * up-front charge and bills the enrolment again for the same period. This adopts
+ * each such up-front charge into the current billing period so the scan treats it
+ * as already billed; later periods bill normally.
+ *
+ * Only the transition *into* scheduled billing is handled — going the other way,
+ * or editing an already-scheduled class, needs no reconciliation. Weekly is left
+ * alone: a weekly class is billed per session as sessions come due, so there is
+ * no single up-front period a prior charge maps onto.
+ */
+class BillingModeReconciler {
+
+	public function __construct(
+		private EnrollmentRepository $enrollments,
+		private PaymentRepository $payments,
+	) {}
+
+	/**
+	 * Reconcile an offering edit. Given the offering as it was and as it now is,
+	 * adopt up-front enrolment charges into the current month when the class has
+	 * just become monthly. Returns the number of charges adopted (0 when the edit
+	 * is not a pay-now -> monthly transition, or nothing needed adopting).
+	 */
+	public function reconcile( Offering $before, Offering $after ): int {
+		if ( null === $after->id || Offering::KIND_GROUP_CLASS !== $after->kind ) {
+			return 0;
+		}
+
+		// Only a fresh switch into monthly scheduling can strand an up-front charge.
+		$becameMonthly = Offering::BILLING_MONTHLY === $after->billingMode
+			&& Offering::BILLING_MONTHLY !== $before->billingMode;
+		if ( ! $becameMonthly ) {
+			return 0;
+		}
+
+		$period  = $this->currentMonth();
+		$dueDate = $period . '-01';
+		$adopted = 0;
+
+		foreach ( $this->enrollments->findActiveByOffering( $after->id ) as $enrollment ) {
+			$enrollmentId = (int) $enrollment->id;
+
+			// Nothing to adopt unless the enrolment holds an up-front (unscheduled)
+			// charge, and never when the scan has already billed this month for it —
+			// adopting then would leave two charges for the month, the opposite of
+			// the fix.
+			if ( ! $this->payments->hasUnscheduledCharge( Payment::REG_ENROLLMENT, $enrollmentId )
+				|| $this->payments->existsForPeriod( Payment::REG_ENROLLMENT, $enrollmentId, $period )
+			) {
+				continue;
+			}
+
+			$adopted += $this->payments->claimPeriodForUnscheduled( Payment::REG_ENROLLMENT, $enrollmentId, $period, $dueDate );
+		}
+
+		return $adopted;
+	}
+
+	/**
+	 * The current calendar month as a `Y-m` period key, from WordPress site time
+	 * so it matches how the billing scan derives its periods.
+	 */
+	private function currentMonth(): string {
+		$mysql = Val::string( current_time( 'mysql' ) );
+
+		return ( false !== strtotime( $mysql ) ? new \DateTimeImmutable( $mysql ) : new \DateTimeImmutable() )->format( 'Y-m' );
+	}
+}

src/Offering/OfferingController.php

@@ -12,6 +12,7 @@ class OfferingController {
 	public function __construct(
 		private OfferingRepository $repository,
 		private ClassSlotReconciler $reconciler,
+		private BillingModeReconciler $billingModeReconciler,
 		private AccessSettings $access = new AccessSettings(),
 	) {}
 
@@ -81,6 +82,11 @@ class OfferingController {
 					if ( null !== $offering ) {
 						$this->repository->update( $offeringId, $offering );
 
+						// Adopt any up-front enrolment charge into the current period when
+						// this edit switched the class to monthly, so the daily scan does
+						// not bill those enrolments a second time for the month.
+						$this->billingModeReconciler->reconcile( $existing, $offering );
+
 						return $this->reconcileNotice( $offering );
 					}
 				}

src/Offering/OfferingEndpoint.php

@@ -13,6 +13,7 @@ class OfferingEndpoint {
 	public function __construct(
 		private OfferingRepository $repository,
 		private GroupAccessRepository $access,
+		private BillingModeReconciler $billingModeReconciler,
 	) {}
 
 	/**
@@ -237,6 +238,11 @@ class OfferingEndpoint {
 
 		$this->repository->update( $id, $offering );
 
+		// Adopt any up-front enrolment charge into the current period when this edit
+		// switched the class to monthly, so the daily scan does not bill those
+		// enrolments a second time for the month.
+		$this->billingModeReconciler->reconcile( $existing, $offering );
+
 		return new \WP_REST_Response( $offering->toArray(), 200 );
 	}
 

src/Payment/PaymentRepository.php

@@ -272,6 +272,61 @@ class PaymentRepository {
 		);
 	}
 
+	/**
+	 * Whether a registration has an unscheduled, un-voided charge — one taken at
+	 * registration (`period_key IS NULL`, `status != failed`). The billing-mode
+	 * reconciler uses this to spot an up-front charge that a newly-scheduled
+	 * offering would otherwise cause the scan to bill a second time.
+	 */
+	public function hasUnscheduledCharge( string $registrationType, int $registrationId ): bool {
+		$found = $this->db->get_var(
+			$this->db->prepare(
+				'SELECT id FROM %i WHERE registration_type = %s AND registration_id = %d AND period_key IS NULL AND status != %s LIMIT 1',
+				$this->table,
+				$registrationType,
+				$registrationId,
+				Payment::STATUS_FAILED
+			)
+		);
+
+		return null !== $found;
+	}
+
+	/**
+	 * Stamp a registration's existing unscheduled charge with a billing period and
+	 * due date so the daily scan treats that period as already billed. Used when
+	 * an offering is switched to scheduled billing: the charge taken at enrolment
+	 * (which carries no `period_key`) would otherwise never match the scan's
+	 * per-period dedup, and the enrolment would be billed a second time for the
+	 * period the up-front charge already covers.
+	 *
+	 * Only ever adopts a charge that is genuinely unscheduled (`period_key IS
+	 * NULL`) and not voided (`status != failed`) — so it cannot overwrite a real
+	 * scheduled charge or revive a cancelled one. The caller guards against a
+	 * period that already has a scheduled charge (see {@see existsForPeriod}).
+	 * Returns the number of rows adopted (0 or 1).
+	 */
+	public function claimPeriodForUnscheduled( string $registrationType, int $registrationId, string $periodKey, string $dueDate ): int {
+		$sql = $this->db->prepare(
+			'UPDATE %i SET period_key = %s, due_date = %s
+			 WHERE registration_type = %s AND registration_id = %d
+			   AND period_key IS NULL AND status != %s
+			 ORDER BY id ASC LIMIT 1',
+			$this->table,
+			$periodKey,
+			$dueDate,
+			$registrationType,
+			$registrationId,
+			Payment::STATUS_FAILED
+		);
+
+		if ( null === $sql ) {
+			return 0;
+		}
+
+		return (int) $this->db->query( $sql );
+	}
+
 	/**
 	 * Atomically claim a payment for its one due-payment notice. Stamps
 	 * `notice_sent_at` only if it is still null, and returns whether *this* call

src/Plugin.php

@@ -24,6 +24,7 @@ use Unsupervised\Schedular\Guardian\ChildLoginGate;
 use Unsupervised\Schedular\Guardian\FamilyPage;
 use Unsupervised\Schedular\Guardian\GuardianRepository;
 use Unsupervised\Schedular\Guardian\GuardianService;
+use Unsupervised\Schedular\Offering\BillingModeReconciler;
 use Unsupervised\Schedular\Offering\OfferingRepository;
 use Unsupervised\Schedular\Payment\BillingMethodResolver;
 use Unsupervised\Schedular\Payment\CreditRepository;
@@ -129,6 +130,11 @@ class Plugin {
 		$familyPage       = new FamilyPage( $guardians, $questions, $answers );
 		$accountPage      = new AccountPage();
 
+		// Adopts an up-front enrolment charge into the current billing period when a
+		// group class is switched to monthly, so the daily scan does not bill it a
+		// second time for a month the up-front charge already covers.
+		$billingModeReconciler = new BillingModeReconciler( $enrollments, $paymentRepo );
+
 		( new ScheduledBillingRunner( $paymentService, $bookings, $enrollments, $offerings, new PaymentDueMailer(), $guardians ) )->register();
 
 		( new UpdateChecker() )->register();
@@ -138,8 +144,8 @@ class Plugin {
 		( new StudentAdminGuard() )->register();
 		( new DeletedUserCleanup( $bookings, $availability, $enrollments, $paymentService, $guardianRepo, $guardians ) )->register();
 		( new EmailConfirmationHandler( $settings, $registrationMailer ) )->register();
-		( new AdminMenu( $availability, $bookings, $offerings, $questions, $answers, $policies, $policyVersions, $policyService, $acceptances, $invites, $enrollments, $groupAccess, $settings, $paymentRepo, $paymentService, $resolver, $registrationMailer, $creditRepo, $guardians, $lessonBooker, $registrationGate ) )->register();
-		( new RestRegistrar( $availability, $bookings, $offerings, $questions, $policies, $policyVersions, $policyService, $registrationGate, $enrollments, $groupAccess, $paymentService, $guardians, $lessonBooker ) )->register();
+		( new AdminMenu( $availability, $bookings, $offerings, $questions, $answers, $policies, $policyVersions, $policyService, $acceptances, $invites, $enrollments, $groupAccess, $settings, $paymentRepo, $paymentService, $resolver, $registrationMailer, $creditRepo, $guardians, $lessonBooker, $registrationGate, $billingModeReconciler ) )->register();
+		( new RestRegistrar( $availability, $bookings, $offerings, $questions, $policies, $policyVersions, $policyService, $registrationGate, $enrollments, $groupAccess, $paymentService, $guardians, $lessonBooker, $billingModeReconciler ) )->register();
 		( new ShortcodeRegistrar( $bookingPage, $loginPage, $registrationPage, $groupClassPage, $familyPage, $accountPage ) )->register();
 		( new BlockRegistrar( $bookingPage, $loginPage, $registrationPage, $groupClassPage, $familyPage, $accountPage ) )->register();
 	}

src/RestRegistrar.php

@@ -15,6 +15,7 @@ use Unsupervised\Schedular\GroupClass\GroupAccessRepository;
 use Unsupervised\Schedular\GroupClass\EnrollmentRepository;
 use Unsupervised\Schedular\GroupClass\SessionSchedule;
 use Unsupervised\Schedular\Guardian\GuardianService;
+use Unsupervised\Schedular\Offering\BillingModeReconciler;
 use Unsupervised\Schedular\Offering\OfferingEndpoint;
 use Unsupervised\Schedular\Offering\OfferingRepository;
 use Unsupervised\Schedular\Payment\PaymentEndpoint;
@@ -40,10 +41,10 @@ class RestRegistrar {
 	private EnrollmentEndpoint $enrollmentEndpoint;
 	private PaymentEndpoint $paymentEndpoint;
 
-	public function __construct( AvailabilityRepository $availability, BookingRepository $bookings, OfferingRepository $offerings, QuestionRepository $questions, PolicyRepository $policies, PolicyVersionRepository $policyVersions, PolicyService $policyService, RegistrationGate $gate, EnrollmentRepository $enrollments, GroupAccessRepository $groupAccess, PaymentService $paymentService, GuardianService $guardians, LessonBooker $booker ) {
+	public function __construct( AvailabilityRepository $availability, BookingRepository $bookings, OfferingRepository $offerings, QuestionRepository $questions, PolicyRepository $policies, PolicyVersionRepository $policyVersions, PolicyService $policyService, RegistrationGate $gate, EnrollmentRepository $enrollments, GroupAccessRepository $groupAccess, PaymentService $paymentService, GuardianService $guardians, LessonBooker $booker, BillingModeReconciler $billingModeReconciler ) {
 		$this->availabilityEndpoint = new AvailabilityEndpoint( $availability, new WindowValidator( $offerings ) );
 		$this->bookingEndpoint      = new BookingEndpoint( $availability, $bookings, $offerings, $gate, $paymentService, $booker, new CancellationPolicy( new StudioSettings() ), $guardians, new SessionSchedule( $enrollments, $offerings ) );
-		$this->offeringEndpoint     = new OfferingEndpoint( $offerings, $groupAccess );
+		$this->offeringEndpoint     = new OfferingEndpoint( $offerings, $groupAccess, $billingModeReconciler );
 		$this->questionEndpoint     = new QuestionEndpoint( $questions, $offerings );
 		$this->policyEndpoint       = new PolicyEndpoint( $policies, $policyVersions, $policyService );
 		$this->enrollmentEndpoint   = new EnrollmentEndpoint( $enrollments, $offerings, $gate, $paymentService, $groupAccess, $guardians );

tests/Unit/GroupClass/EnrollmentRepositoryTest.php

@@ -110,6 +110,35 @@ class EnrollmentRepositoryTest extends TestCase
         self::assertInstanceOf(Enrollment::class, $all[0]);
     }
 
+    public function testFindActiveByOfferingReturnsActiveEnrolmentsOldestFirst(): void
+    {
+        $this->db->shouldReceive('prepare')
+            ->once()
+            ->with(
+                Mockery::pattern('/offering_id = %d AND status = %s ORDER BY id ASC/'),
+                'wp_us_group_enrollments',
+                9,
+                Enrollment::STATUS_ACTIVE
+            )
+            ->andReturn('SELECT ...');
+
+        $this->db->shouldReceive('get_results')->andReturn([
+            (object) [
+                'id'            => '7',
+                'offering_id'   => '9',
+                'student_id'    => '5',
+                'instructor_id' => '3',
+                'status'        => Enrollment::STATUS_ACTIVE,
+                'payment_id'    => null,
+            ],
+        ]);
+
+        $found = $this->repo->findActiveByOffering(9);
+
+        self::assertCount(1, $found);
+        self::assertSame(7, $found[0]->id);
+    }
+
     public function testFindActiveByBillingModesJoinsOfferingAndFiltersModes(): void
     {
         $this->db->shouldReceive('prepare')

tests/Unit/Offering/BillingModeReconcilerTest.php

@@ -0,0 +1,136 @@
+<?php
+declare(strict_types=1);
+
+namespace Unsupervised\Schedular\Tests\Unit\Offering;
+
+use Brain\Monkey\Functions;
+use Mockery;
+use Unsupervised\Schedular\GroupClass\Enrollment;
+use Unsupervised\Schedular\GroupClass\EnrollmentRepository;
+use Unsupervised\Schedular\Offering\BillingModeReconciler;
+use Unsupervised\Schedular\Offering\Offering;
+use Unsupervised\Schedular\Payment\Payment;
+use Unsupervised\Schedular\Payment\PaymentRepository;
+use Unsupervised\Schedular\Tests\Unit\TestCase;
+
+class BillingModeReconcilerTest extends TestCase
+{
+    private EnrollmentRepository&Mockery\MockInterface $enrollments;
+    private PaymentRepository&Mockery\MockInterface $payments;
+    private BillingModeReconciler $reconciler;
+
+    protected function setUp(): void
+    {
+        parent::setUp();
+
+        Functions\when('current_time')->justReturn('2026-09-15 09:00:00');
+
+        $this->enrollments = Mockery::mock(EnrollmentRepository::class);
+        $this->payments    = Mockery::mock(PaymentRepository::class);
+        $this->reconciler  = new BillingModeReconciler($this->enrollments, $this->payments);
+    }
+
+    private function offering(string $billingMode, ?int $id = 9): Offering
+    {
+        return new Offering(
+            instructorId: 3,
+            kind:         Offering::KIND_GROUP_CLASS,
+            title:        'Ensemble',
+            price:        150.0,
+            billingMode:  $billingMode,
+            id:           $id,
+        );
+    }
+
+    private function enrollment(int $id, int $studentId = 5): Enrollment
+    {
+        return new Enrollment(offeringId: 9, studentId: $studentId, instructorId: 3, id: $id);
+    }
+
+    public function testAdoptsUpfrontChargeIntoCurrentMonthWhenClassBecomesMonthly(): void
+    {
+        $this->enrollments->shouldReceive('findActiveByOffering')->with(9)->andReturn([$this->enrollment(7)]);
+
+        $this->payments->shouldReceive('hasUnscheduledCharge')->with(Payment::REG_ENROLLMENT, 7)->andReturn(true);
+        $this->payments->shouldReceive('existsForPeriod')->with(Payment::REG_ENROLLMENT, 7, '2026-09')->andReturn(false);
+
+        // The up-front charge is stamped into 2026-09, due on the 1st, so the scan
+        // treats September as already billed for this enrolment.
+        $this->payments->shouldReceive('claimPeriodForUnscheduled')
+            ->once()
+            ->with(Payment::REG_ENROLLMENT, 7, '2026-09', '2026-09-01')
+            ->andReturn(1);
+
+        self::assertSame(1, $this->reconciler->reconcile($this->offering(Offering::BILLING_ONE_TIME), $this->offering(Offering::BILLING_MONTHLY)));
+    }
+
+    public function testDoesNothingWhenBillingModeDidNotChangeIntoMonthly(): void
+    {
+        $this->enrollments->shouldNotReceive('findActiveByOffering');
+        $this->payments->shouldNotReceive('claimPeriodForUnscheduled');
+
+        // Already monthly -> monthly (e.g. an unrelated title edit): no transition.
+        self::assertSame(0, $this->reconciler->reconcile($this->offering(Offering::BILLING_MONTHLY), $this->offering(Offering::BILLING_MONTHLY)));
+    }
+
+    public function testDoesNothingWhenSwitchingToWeekly(): void
+    {
+        $this->enrollments->shouldNotReceive('findActiveByOffering');
+        $this->payments->shouldNotReceive('claimPeriodForUnscheduled');
+
+        // Weekly bills per session as sessions come due; there is no single upfront
+        // period an enrolment charge maps onto, so it is left alone.
+        self::assertSame(0, $this->reconciler->reconcile($this->offering(Offering::BILLING_ONE_TIME), $this->offering(Offering::BILLING_WEEKLY)));
+    }
+
+    public function testSkipsEnrolmentWithoutAnUpfrontCharge(): void
+    {
+        $this->enrollments->shouldReceive('findActiveByOffering')->with(9)->andReturn([$this->enrollment(7)]);
+
+        // Enrolled after the class was already scheduled, or never charged upfront:
+        // nothing to adopt.
+        $this->payments->shouldReceive('hasUnscheduledCharge')->with(Payment::REG_ENROLLMENT, 7)->andReturn(false);
+        $this->payments->shouldNotReceive('claimPeriodForUnscheduled');
+
+        self::assertSame(0, $this->reconciler->reconcile($this->offering(Offering::BILLING_ONE_TIME), $this->offering(Offering::BILLING_MONTHLY)));
+    }
+
+    public function testSkipsEnrolmentAlreadyBilledForThisMonthByTheScan(): void
+    {
+        $this->enrollments->shouldReceive('findActiveByOffering')->with(9)->andReturn([$this->enrollment(7)]);
+
+        $this->payments->shouldReceive('hasUnscheduledCharge')->with(Payment::REG_ENROLLMENT, 7)->andReturn(true);
+        // The scan already made a 2026-09 charge: adopting the upfront one too would
+        // leave two charges for the month — the very thing we are preventing.
+        $this->payments->shouldReceive('existsForPeriod')->with(Payment::REG_ENROLLMENT, 7, '2026-09')->andReturn(true);
+        $this->payments->shouldNotReceive('claimPeriodForUnscheduled');
+
+        self::assertSame(0, $this->reconciler->reconcile($this->offering(Offering::BILLING_ONE_TIME), $this->offering(Offering::BILLING_MONTHLY)));
+    }
+
+    public function testReconcilesEveryActiveEnrolment(): void
+    {
+        $this->enrollments->shouldReceive('findActiveByOffering')->with(9)
+            ->andReturn([$this->enrollment(7, 5), $this->enrollment(8, 6)]);
+
+        $this->payments->shouldReceive('hasUnscheduledCharge')->with(Payment::REG_ENROLLMENT, 7)->andReturn(true);
+        $this->payments->shouldReceive('existsForPeriod')->with(Payment::REG_ENROLLMENT, 7, '2026-09')->andReturn(false);
+        $this->payments->shouldReceive('claimPeriodForUnscheduled')->with(Payment::REG_ENROLLMENT, 7, '2026-09', '2026-09-01')->andReturn(1);
+
+        $this->payments->shouldReceive('hasUnscheduledCharge')->with(Payment::REG_ENROLLMENT, 8)->andReturn(true);
+        $this->payments->shouldReceive('existsForPeriod')->with(Payment::REG_ENROLLMENT, 8, '2026-09')->andReturn(false);
+        $this->payments->shouldReceive('claimPeriodForUnscheduled')->with(Payment::REG_ENROLLMENT, 8, '2026-09', '2026-09-01')->andReturn(1);
+
+        self::assertSame(2, $this->reconciler->reconcile($this->offering(Offering::BILLING_ONE_TIME), $this->offering(Offering::BILLING_MONTHLY)));
+    }
+
+    public function testIgnoresNonGroupClassOfferings(): void
+    {
+        $before = new Offering(instructorId: 3, kind: Offering::KIND_PRIVATE_LESSON, title: 'Piano', billingMode: Offering::BILLING_ONE_TIME, id: 9);
+        $after  = new Offering(instructorId: 3, kind: Offering::KIND_PRIVATE_LESSON, title: 'Piano', billingMode: Offering::BILLING_MONTHLY, id: 9);
+
+        $this->enrollments->shouldNotReceive('findActiveByOffering');
+
+        self::assertSame(0, $this->reconciler->reconcile($before, $after));
+    }
+}

tests/Unit/Offering/OfferingControllerTest.php

@@ -5,6 +5,7 @@ namespace Unsupervised\Schedular\Tests\Unit\Offering;
 
 use Brain\Monkey\Functions;
 use Mockery;
+use Unsupervised\Schedular\Offering\BillingModeReconciler;
 use Unsupervised\Schedular\Offering\ClassSlotReconciler;
 use Unsupervised\Schedular\Offering\Offering;
 use Unsupervised\Schedular\Offering\OfferingController;
@@ -15,6 +16,7 @@ class OfferingControllerTest extends TestCase
 {
     private OfferingRepository&Mockery\MockInterface $repository;
     private ClassSlotReconciler&Mockery\MockInterface $reconciler;
+    private BillingModeReconciler&Mockery\MockInterface $billingModeReconciler;
     private OfferingController $controller;
 
     protected function setUp(): void
@@ -24,7 +26,9 @@ class OfferingControllerTest extends TestCase
         $this->repository = Mockery::mock(OfferingRepository::class);
         $this->reconciler = Mockery::mock(ClassSlotReconciler::class);
         $this->reconciler->shouldReceive('reconcile')->andReturn(['removed' => 0, 'conflicts' => []])->byDefault();
-        $this->controller = new OfferingController($this->repository, $this->reconciler);
+        $this->billingModeReconciler = Mockery::mock(BillingModeReconciler::class);
+        $this->billingModeReconciler->shouldReceive('reconcile')->andReturn(0)->byDefault();
+        $this->controller = new OfferingController($this->repository, $this->reconciler, $this->billingModeReconciler);
 
         $_POST = [];
         $_GET  = [];

tests/Unit/Offering/OfferingEndpointTest.php

@@ -7,6 +7,7 @@ use Brain\Monkey\Functions;
 use Mockery;
 use Unsupervised\Schedular\Auth\RoleManager;
 use Unsupervised\Schedular\GroupClass\GroupAccessRepository;
+use Unsupervised\Schedular\Offering\BillingModeReconciler;
 use Unsupervised\Schedular\Offering\Offering;
 use Unsupervised\Schedular\Offering\OfferingEndpoint;
 use Unsupervised\Schedular\Offering\OfferingRepository;
@@ -16,6 +17,7 @@ class OfferingEndpointTest extends TestCase
 {
     private OfferingRepository&Mockery\MockInterface $repository;
     private GroupAccessRepository&Mockery\MockInterface $access;
+    private BillingModeReconciler&Mockery\MockInterface $billingModeReconciler;
     private OfferingEndpoint $endpoint;
 
     protected function setUp(): void
@@ -27,7 +29,9 @@ class OfferingEndpointTest extends TestCase
 
         $this->repository = Mockery::mock(OfferingRepository::class);
         $this->access     = Mockery::mock(GroupAccessRepository::class);
-        $this->endpoint   = new OfferingEndpoint($this->repository, $this->access);
+        $this->billingModeReconciler = Mockery::mock(BillingModeReconciler::class);
+        $this->billingModeReconciler->shouldReceive('reconcile')->andReturn(0)->byDefault();
+        $this->endpoint   = new OfferingEndpoint($this->repository, $this->access, $this->billingModeReconciler);
     }
 
     private function group(int $id, string $access): Offering

tests/Unit/Payment/PaymentRepositoryTest.php

@@ -179,6 +179,52 @@ class PaymentRepositoryTest extends TestCase
         self::assertFalse($this->repo->backfillNoticeSent());
     }
 
+    public function testHasUnscheduledChargeTrueWhenUpfrontChargeExists(): void
+    {
+        $this->db->shouldReceive('prepare')
+            ->once()
+            ->with(Mockery::pattern('/period_key IS NULL AND status != %s/'), 'wp_us_payments', Payment::REG_ENROLLMENT, 7, Payment::STATUS_FAILED)
+            ->andReturn('SELECT ...');
+        $this->db->shouldReceive('get_var')->once()->with('SELECT ...')->andReturn('3');
+
+        self::assertTrue($this->repo->hasUnscheduledCharge(Payment::REG_ENROLLMENT, 7));
+    }
+
+    public function testHasUnscheduledChargeFalseWhenNoneOrOnlyVoided(): void
+    {
+        $this->db->shouldReceive('prepare')->once()->andReturn('SELECT ...');
+        $this->db->shouldReceive('get_var')->once()->andReturn(null);
+
+        self::assertFalse($this->repo->hasUnscheduledCharge(Payment::REG_ENROLLMENT, 7));
+    }
+
+    public function testClaimPeriodForUnscheduledStampsPeriodAndDueDate(): void
+    {
+        $this->db->shouldReceive('prepare')
+            ->once()
+            ->with(
+                Mockery::pattern('/SET period_key = %s, due_date = %s.*period_key IS NULL AND status != %s/s'),
+                'wp_us_payments',
+                '2026-09',
+                '2026-09-01',
+                Payment::REG_ENROLLMENT,
+                7,
+                Payment::STATUS_FAILED
+            )
+            ->andReturn('UPDATE ...');
+        $this->db->shouldReceive('query')->once()->with('UPDATE ...')->andReturn(1);
+
+        self::assertSame(1, $this->repo->claimPeriodForUnscheduled(Payment::REG_ENROLLMENT, 7, '2026-09', '2026-09-01'));
+    }
+
+    public function testClaimPeriodForUnscheduledAdoptsNothingWhenNoMatch(): void
+    {
+        $this->db->shouldReceive('prepare')->once()->andReturn('UPDATE ...');
+        $this->db->shouldReceive('query')->once()->with('UPDATE ...')->andReturn(0);
+
+        self::assertSame(0, $this->repo->claimPeriodForUnscheduled(Payment::REG_ENROLLMENT, 7, '2026-09', '2026-09-01'));
+    }
+
     public function testUpdateTaxRecomputesAmountFromRate(): void
     {
         $this->db->shouldReceive('prepare')