diff --git a/C4/Circulation.pm b/C4/Circulation.pm
index e4c76fb5f8..211de86d21 100644
--- a/C4/Circulation.pm
+++ b/C4/Circulation.pm
@@ -864,6 +864,7 @@ sub CanBookBeIssued {
 
     my $now = dt_from_string();
 
+    my $requested_duedate = $duedate ? 1 : 0;
     $duedate ||= CalcDateDue( $now, $effective_itemtype, $circ_library->branchcode, $patron );
 
     if ( DateTime->compare( $duedate, $now ) == -1 ) {    # duedate cannot be before now
@@ -1327,6 +1328,21 @@ sub CanBookBeIssued {
             } else {
                 $alerts{'BOOKED'} = $booking;
             }
+
+            # An explicitly requested due date that runs into the next booking
+            # for this item, regardless of whose booking that is, needs staff
+            # confirmation; the booking end date will not be extended past that
+            # booking (see AddIssue)
+            if ($requested_duedate) {
+                my $next_booking = $item_object->find_booking(
+                    {
+                        checkout_date      => $now,
+                        due_date           => $duedate,
+                        exclude_booking_id => $booking->booking_id,
+                    }
+                );
+                $needsconfirmation{'BOOKED_DUE_DATE_CLASH'} = $next_booking if $next_booking;
+            }
         }
 
         # Booked to another patron
diff --git a/Koha/Item.pm b/Koha/Item.pm
index eb19468653..a5599caab6 100644
--- a/Koha/Item.pm
+++ b/Koha/Item.pm
@@ -629,12 +629,17 @@ sub bookings {
 
 =head3 find_booking
 
-  my $booking = $item->find_booking( { checkout_date => $now, due_date => $future_date } );
+  my $booking = $item->find_booking(
+      { checkout_date => $now, due_date => $future_date, [ exclude_booking_id => $booking_id ] } );
 
 Find the first booking that would conflict with the passed checkout dates for this item.  If a booking
 lead period is configured for the itemtype we will also take that into account here, counting bookings
 that fall in that lead period as conflicts too.
 
+Optionally, you may pass an exclude_booking_id to leave a specific booking out of the checks; this is
+helpful when looking for bookings that would clash with an extension of the checkout that is already
+satisfying that booking.
+
 FIXME: This can be simplified, it was originally intended to iterate all biblio level bookings
 to catch cases where this item may be the last available to satisfy a biblio level only booking.
 However, we dropped the biblio level functionality prior to push as bugs were found in it's
@@ -645,9 +650,10 @@ implementation.
 sub find_booking {
     my ( $self, $params ) = @_;
 
-    my $start_date = $params->{checkout_date};
-    my $end_date   = $params->{due_date};
-    my $biblio     = $self->biblio;
+    my $start_date         = $params->{checkout_date};
+    my $end_date           = $params->{due_date};
+    my $exclude_booking_id = $params->{exclude_booking_id};
+    my $biblio             = $self->biblio;
 
     my $rule = Koha::CirculationRules->get_effective_rule(
         {
@@ -689,7 +695,8 @@ sub find_booking {
                         }
                     ]
                 },
-                { status => { '-not_in' => [ 'cancelled', 'completed' ] } }
+                { status => { '-not_in' => [ 'cancelled', 'completed' ] } },
+                ( $exclude_booking_id ? { booking_id => { '!=' => $exclude_booking_id } } : () ),
             ]
         },
         { order_by => { '-asc' => 'start_date' } }
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 4a74a2b403..39f1c61ec8 100644
--- a/koha-tmpl/intranet-tmpl/prog/en/modules/circ/circulation.tt
+++ b/koha-tmpl/intranet-tmpl/prog/en/modules/circ/circulation.tt
@@ -317,6 +317,13 @@
                 [% IF ( BOOKED_EARLY ) %]
                     <li class="needsconfirm booked_early"> Patron has this item booked for checkout on [% BOOKED_EARLY.start_date | $KohaDates %] </li>
                 [% END %]
+
+                [% IF ( BOOKED_DUE_DATE_CLASH ) %]
+                    <li class="needsconfirm booked_due_date_clash">
+                        The requested due date falls within the next booking for this item (booked from [% BOOKED_DUE_DATE_CLASH.start_date | $KohaDates %]). If you continue, the booking linked to this checkout will keep its original end
+                        date.
+                    </li>
+                [% END %]
             </ul>
 
             [% IF CAN_user_circulate_force_checkout or HIGHHOLDS %]
diff --git a/t/db_dependent/Circulation.t b/t/db_dependent/Circulation.t
index 1974c2efa8..7564d18d90 100755
--- a/t/db_dependent/Circulation.t
+++ b/t/db_dependent/Circulation.t
@@ -5711,7 +5711,7 @@ subtest 'CanBookBeIssued | recalls' => sub {
 };
 
 subtest 'CanBookBeIssued | bookings' => sub {
-    plan tests => 4;
+    plan tests => 7;
 
     my $schema = Koha::Database->schema;
     $schema->storage->txn_begin;
@@ -5780,6 +5780,50 @@ subtest 'CanBookBeIssued | bookings' => sub {
         "Booked to this user, but they're collecting early"
     );
 
+    # Requested due date runs into the next booking for this item
+    $booking->start_date( dt_from_string()->subtract( days => 1 ) )->store();
+
+    my $subsequent_booking = Koha::Booking->new(
+        {
+            patron_id         => $patron2->borrowernumber,
+            pickup_library_id => $pickup_library->branchcode,
+            item_id           => $item->itemnumber,
+            biblio_id         => $item->biblio->biblionumber,
+            start_date        => dt_from_string()->add( days => 8 ),
+            end_date          => dt_from_string()->add( days => 12 ),
+        }
+    )->store();
+
+    ( $issuingimpossible, $needsconfirmation, $alerts, $messages ) = CanBookBeIssued(
+        $patron1, $item->barcode,
+        dt_from_string()->add( days => 9 ),
+        undef, undef, undef
+    );
+    is(
+        $needsconfirmation->{BOOKED_DUE_DATE_CLASH}->booking_id,
+        $subsequent_booking->booking_id,
+        "Requested due date running into the next booking needs confirmation"
+    );
+
+    ( $issuingimpossible, $needsconfirmation, $alerts, $messages ) = CanBookBeIssued(
+        $patron1, $item->barcode,
+        dt_from_string()->add( days => 5 ),
+        undef, undef, undef
+    );
+    is(
+        $needsconfirmation->{BOOKED_DUE_DATE_CLASH}, undef,
+        "No confirmation needed when the requested due date stays clear of the next booking"
+    );
+
+    ( $issuingimpossible, $needsconfirmation, $alerts, $messages ) = CanBookBeIssued(
+        $patron1, $item->barcode,
+        undef,    undef, undef, undef
+    );
+    is(
+        $needsconfirmation->{BOOKED_DUE_DATE_CLASH}, undef,
+        "No confirmation triggered by a calculated due date; only explicit overrides are checked"
+    );
+
     $schema->storage->txn_rollback;
 };
 
diff --git a/t/db_dependent/Koha/Item.t b/t/db_dependent/Koha/Item.t
index 3f1dc11c97..12f9409e15 100755
--- a/t/db_dependent/Koha/Item.t
+++ b/t/db_dependent/Koha/Item.t
@@ -3499,7 +3499,7 @@ subtest 'bookings' => sub {
 };
 
 subtest 'find_booking' => sub {
-    plan tests => 9;
+    plan tests => 11;
 
     $schema->storage->txn_begin;
 
@@ -3606,6 +3606,31 @@ subtest 'find_booking' => sub {
         "Koha::Item->find_booking returns the current booking not a future one"
     );
 
+    # Exclusion of a specific booking
+    $found_booking = $item->find_booking(
+        {
+            checkout_date      => dt_from_string(),
+            due_date           => dt_from_string()->add( days => 7 ),
+            exclude_booking_id => $booking2->booking_id,
+        }
+    );
+    is(
+        $found_booking, undef,
+        "Koha::Item->find_booking skips the excluded booking when nothing else clashes"
+    );
+
+    $found_booking = $item->find_booking(
+        {
+            checkout_date      => dt_from_string(),
+            due_date           => dt_from_string()->add( days => 9 ),
+            exclude_booking_id => $booking2->booking_id,
+        }
+    );
+    is(
+        $found_booking->booking_id, $booking3->booking_id,
+        "Koha::Item->find_booking returns the next clashing booking when the excluded one is skipped"
+    );
+
     # Cancelled booking
     $booking2->status('cancelled')->store();
     $found_booking = $item->find_booking(