diff --git a/circ/circulation.pl b/circ/circulation.pl
index d61c4851f2..a6b7416f54 100755
--- a/circ/circulation.pl
+++ b/circ/circulation.pl
@@ -629,6 +629,17 @@ if ( $patron ) {
     );
     $template->param( patron_messages => $patron_messages );
 
+    if ( C4::Context->preference("WaitingNotifyAtCheckout") ) {
+
+        #Check for waiting holds
+        my $waiting_holds          = $patron->holds->search( { found => 'W', branchcode => $branch } );
+        my @waiting_holds_barcodes = ();
+        while ( my $hold = $waiting_holds->next ) {
+            push( @waiting_holds_barcodes, $hold->item->barcode );
+        }
+
+        $template->param( waiting_holds_barcodes => \@waiting_holds_barcodes );
+    }
 }
 
 my $fast_cataloging = 0;
diff --git a/installer/data/mysql/atomicupdate/bug_34668-add_WaitingNotifyAtCheckout_syspref.pl b/installer/data/mysql/atomicupdate/bug_34668-add_WaitingNotifyAtCheckout_syspref.pl
new file mode 100644
index 0000000000..d7a8848ed3
--- /dev/null
+++ b/installer/data/mysql/atomicupdate/bug_34668-add_WaitingNotifyAtCheckout_syspref.pl
@@ -0,0 +1,16 @@
+use Modern::Perl;
+
+return {
+    bug_number  => "34668",
+    description => "Add syspref WaitingNotifyAtCheckout",
+    up          => sub {
+        my ($args) = @_;
+        my ( $dbh, $out ) = @$args{qw(dbh out)};
+
+        # Do you stuffs here
+        $dbh->do(q{INSERT IGNORE INTO `systempreferences` (variable,value,options,explanation,type) VALUES('WaitingNotifyAtCheckout','0',NULL,'If ON, notify librarians of waiting holds for the patron whose items they are checking out.','YesNo') });
+
+        say $out "Added new system preference 'WaitingNotifyAtCheckout'";
+
+    },
+};
diff --git a/installer/data/mysql/mandatory/sysprefs.sql b/installer/data/mysql/mandatory/sysprefs.sql
index 902cf7db2e..4057841a34 100644
--- a/installer/data/mysql/mandatory/sysprefs.sql
+++ b/installer/data/mysql/mandatory/sysprefs.sql
@@ -828,6 +828,7 @@ INSERT INTO systempreferences ( `variable`, `value`, `options`, `explanation`, `
 ('viewMARC','1','','Allow display of MARC view of bibiographic records','YesNo'),
 ('virtualshelves','1','','If ON, enables Lists management','YesNo'),
 ('WaitingNotifyAtCheckin','0',NULL,'If ON, notify librarians of waiting holds for the patron whose items they are checking in.','YesNo'),
+('WaitingNotifyAtCheckout','0',NULL,'If ON, notify librarians of waiting holds for the patron whose items they are checking out.','YesNo'),
 ('WebBasedSelfCheck','0',NULL,'If ON, enables the web-based self-check system','YesNo'),
 ('WhenLostChargeReplacementFee','1',NULL,'If ON, Charge the replacement price when a patron loses an item.','YesNo'),
 ('WhenLostForgiveFine','0',NULL,'If ON, Forgives the fines on an item when it is lost.','YesNo'),
diff --git a/koha-tmpl/intranet-tmpl/prog/en/modules/admin/preferences/circulation.pref b/koha-tmpl/intranet-tmpl/prog/en/modules/admin/preferences/circulation.pref
index bae185a1f5..b9169b203f 100644
--- a/koha-tmpl/intranet-tmpl/prog/en/modules/admin/preferences/circulation.pref
+++ b/koha-tmpl/intranet-tmpl/prog/en/modules/admin/preferences/circulation.pref
@@ -97,6 +97,12 @@ Circulation:
                   1: Notify
                   0: "Don't notify"
             - librarians of waiting holds for the patron whose items they are checking in.
+        -
+            - pref: WaitingNotifyAtCheckout
+              choices:
+                  1: Notify
+                  0: "Don't notify"
+            - librarians of waiting holds for the patron whose items they are checking out.
         -
             - pref: FilterBeforeOverdueReport
               choices:
diff --git a/koha-tmpl/intranet-tmpl/prog/en/modules/circ/circulation.tt b/koha-tmpl/intranet-tmpl/prog/en/modules/circ/circulation.tt
index 54c4da8d89..4cab65fc5a 100644
--- a/koha-tmpl/intranet-tmpl/prog/en/modules/circ/circulation.tt
+++ b/koha-tmpl/intranet-tmpl/prog/en/modules/circ/circulation.tt
@@ -762,7 +762,11 @@
                                             <a href="#" title="Checkout settings"><i class="fa-solid fa-sliders"></i></a>
                                         </div>
 
-                                        <button type="submit" class="btn btn-primary">Check out</button>
+                                        [% IF waiting_holds_barcodes %]
+                                            <button type="button" class="btn btn-primary">Check out</button>
+                                        [% ELSE %]
+                                            <button type="submit" class="btn btn-primary">Check out</button>
+                                        [% END %]
 
                                         <div class="circ-settings">
 
@@ -961,6 +965,28 @@
     </div> <!-- /.modal-dialog -->
 </div> <!-- /#barcodeSubmittedModal -->
 
+[% IF waiting_holds_barcodes %]
+    <div id="circ-warnwaitingholds-modal" class="modal fade audio-alert-action block">
+        <div class="modal-dialog">
+            <div class="modal-content">
+                <div class="modal-header">
+                    <h3>This patron has waiting holds</h3>
+                </div>
+                <div class="modal-body">
+                    <ul>
+                        <li>
+                            This patron has waiting holds that are available for checkout
+                        </li>
+                    </ul>
+                </div>
+                <div class="modal-footer">
+                    <button type="button" class="btn btn-primary" data-dismiss="modal">Ok</button>
+                </div>
+            </div>
+        </div>
+    </div>
+[% END %]
+
 [% MACRO jsinclude BLOCK %]
     [% INCLUDE 'datatables.inc' %]
     [% INCLUDE 'columns_settings.inc' %]
@@ -1028,6 +1054,42 @@
             var newin = window.open(link, 'popup', 'width=600,height=400,resizable=1,toolbar=0,scrollbars=1,top');
         }
         $(document).ready(function() {
+            [% IF waiting_holds_barcodes %]
+                $('#circ-warnwaitingholds-modal .btn-primary').on('click',function() {
+                    $('#mainform').submit();
+                });
+
+                var waiting_holds_barcodes = new Array();
+                [% FOREACH b IN waiting_holds_barcodes %]
+                    waiting_holds_barcodes.push("[% b | html %]");
+                [% END %]
+                $('#barcode').on('keyup', function() {
+                    $('#mainform .btn-primary').off('click');
+                    $('#barcode').off('keypress');
+                    if ( waiting_holds_barcodes.includes($('#barcode').val().trim()) ) {
+                        $('#mainform .btn-primary').on('click',function() {
+                            $('#mainform').submit();
+                        });
+
+                        $('#barcode').on('keypress', function(e) {
+                            if (e.which == 13) {
+                                $('#mainform').submit();
+                            }
+                        });
+                    } else {
+                        $('#mainform .btn-primary').on('click',function() {
+                            $('#circ-warnwaitingholds-modal').modal();
+                        });
+
+                        $('#barcode').on('keypress', function(e) {
+                            if (e.which == 13) {
+                                $('#circ-warnwaitingholds-modal').modal();
+                            }
+                        });
+                    }
+                });
+            [% END %]
+
             $('#mainform').on('submit',function() {
                 if ($("#barcode") && $("#barcode").val()) {
                     $('#barcode').on('keypress',function(event) {