diff --git a/C4/Circulation.pm b/C4/Circulation.pm
index 645189a7f1..20359da039 100644
--- a/C4/Circulation.pm
+++ b/C4/Circulation.pm
@@ -1877,7 +1877,15 @@ sub AddIssue {
                             # Sync any due date override back to the booking end_date so the
                             # booking and checkout agree from the moment of issue
                             my $booking_end = dt_from_string( $booking->end_date );
-                            $booking->end_date($datedue) if $datedue->compare($booking_end) != 0;
+                            if ( $datedue->compare($booking_end) != 0 ) {
+                                $booking->end_date($datedue);
+
+                                # An early collection can be due back before the booked period
+                                # even starts; pull the start_date back to the checkout date
+                                # rather than storing an inverted booking period
+                                my $booking_start = dt_from_string( $booking->start_date );
+                                $booking->start_date($issuedate) if $datedue->compare($booking_start) < 0;
+                            }
 
                             try {
                                 $booking->store;
@@ -3750,7 +3758,14 @@ sub AddRenewal {
                     my $booking_end = dt_from_string( $booking->end_date );
                     if ( $datedue->compare($booking_end) != 0 ) {
                         try {
-                            $booking->end_date($datedue)->store;
+                            $booking->end_date($datedue);
+
+                            # As at issue time, guard against inverting the booking period
+                            # when the new due date precedes the booking start
+                            my $booking_start = dt_from_string( $booking->start_date );
+                            $booking->start_date( dt_from_string( $issue->issuedate ) )
+                                if $datedue->compare($booking_start) < 0;
+                            $booking->store;
                         } catch {
                             my $error = $_;
                             if ( blessed $error && $error->isa('Koha::Exceptions::Booking::Clash') ) {
diff --git a/t/db_dependent/Circulation.t b/t/db_dependent/Circulation.t
index 2ee4702169..ef16239dd4 100755
--- a/t/db_dependent/Circulation.t
+++ b/t/db_dependent/Circulation.t
@@ -7539,7 +7539,7 @@ subtest 'AddIssue/AddReturn | booking status handling' => sub {
 };
 
 subtest 'AddIssue | booking end_date sync with due date override' => sub {
-    plan tests => 5;
+    plan tests => 8;
 
     my $schema = Koha::Database->schema;
     $schema->storage->txn_begin;
@@ -7627,6 +7627,45 @@ subtest 'AddIssue | booking end_date sync with due date override' => sub {
         "Booking end_date kept when override would clash with a subsequent booking"
     );
 
+    AddReturn( $item->barcode, $pickup_library->branchcode );
+    $booking->delete();
+    $subsequent_booking->delete();
+
+    # Case 4: Early collection due back before the booking starts - the
+    # start_date follows the checkout so the period is not inverted
+    Koha::CirculationRules->set_rule(
+        {
+            branchcode => '*',
+            itemtype   => $item->effective_itemtype,
+            rule_name  => 'bookings_lead_period',
+            rule_value => 5,
+        }
+    );
+
+    $booking = Koha::Booking->new(
+        {
+            patron_id         => $patron->borrowernumber,
+            pickup_library_id => $pickup_library->branchcode,
+            item_id           => $item->itemnumber,
+            biblio_id         => $item->biblio->biblionumber,
+            start_date        => dt_from_string()->add( days => 3 ),
+            end_date          => dt_from_string()->add( days => 10 ),
+        }
+    )->store();
+
+    my $early_due   = dt_from_string()->add( days => 1 )->truncate( to => 'minute' );
+    my $early_issue = AddIssue( $patron, $item->barcode, $early_due->clone );
+    $booking->discard_changes();
+    is( $booking->status, 'issued', "Booking marked issued when collected early" );
+    is(
+        dt_from_string( $booking->end_date )->compare($early_due), 0,
+        "Booking end_date synced to an override before the booking start"
+    );
+    is(
+        $booking->start_date, $early_issue->issuedate,
+        "Booking start_date pulled back to the checkout date instead of storing an inverted period"
+    );
+
     $schema->storage->txn_rollback;
 };
 
@@ -7841,7 +7880,7 @@ subtest 'AddRenewal | booking_id preservation' => sub {
 };
 
 subtest 'AddRenewal | booking end_date sync' => sub {
-    plan tests => 4;
+    plan tests => 6;
 
     my $schema = Koha::Database->schema;
     $schema->storage->txn_begin;
@@ -7938,6 +7977,33 @@ subtest 'AddRenewal | booking end_date sync' => sub {
         "Booking end_date kept when the renewal clashes with the next booking"
     );
 
+    # A renewal due before the booking start pulls the start_date back too
+    $booking->set(
+        {
+            start_date => dt_from_string()->add( days => 5 ),
+            end_date   => dt_from_string()->add( days => 8 ),
+        }
+    )->store;
+
+    my $short_due_date = dt_from_string()->add( days => 2 )->truncate( to => 'minute' );
+    AddRenewal(
+        {
+            borrowernumber => $patron->borrowernumber,
+            itemnumber     => $item->itemnumber,
+            branch         => $library->branchcode,
+            datedue        => $short_due_date->clone,
+        }
+    );
+    $booking->discard_changes;
+    is(
+        dt_from_string( $booking->end_date )->compare($short_due_date), 0,
+        "Booking end_date synced to a renewal due date before the booking start"
+    );
+    is(
+        $booking->start_date, $issue->get_from_storage->issuedate,
+        "Booking start_date pulled back to the checkout date instead of storing an inverted period"
+    );
+
     $schema->storage->txn_rollback;
 };