diff --git a/modules/account_stock_anglo_saxon/tests/scenario_account_stock_anglo_saxon.rst b/modules/account_stock_anglo_saxon/tests/scenario_account_stock_anglo_saxon.rst
index d37825382a..2a6a5ca16d 100644
--- a/modules/account_stock_anglo_saxon/tests/scenario_account_stock_anglo_saxon.rst
+++ b/modules/account_stock_anglo_saxon/tests/scenario_account_stock_anglo_saxon.rst
@@ -244,7 +244,6 @@ Send 5 products::
     >>> ShipmentOut = Model.get('stock.shipment.out')
     >>> shipment, = sale.shipments
     >>> shipment.click('assign_try')
-    True
     >>> shipment.state
     'assigned'
     >>> shipment.click('pick')
diff --git a/modules/account_stock_continental/tests/scenario_account_stock_continental.rst b/modules/account_stock_continental/tests/scenario_account_stock_continental.rst
index 6b9e51eeea..416aa2f8af 100644
--- a/modules/account_stock_continental/tests/scenario_account_stock_continental.rst
+++ b/modules/account_stock_continental/tests/scenario_account_stock_continental.rst
@@ -206,7 +206,6 @@ Send 5 products::
 
     >>> shipment, = sale.shipments
     >>> shipment.click('assign_try')
-    True
     >>> shipment.state
     'assigned'
     >>> shipment.click('pick')
diff --git a/modules/production/CHANGELOG b/modules/production/CHANGELOG
index 3da1cd999d..da70da7262 100644
--- a/modules/production/CHANGELOG
+++ b/modules/production/CHANGELOG
@@ -1,3 +1,5 @@
+* Assign all possible productions when trying
+
 Version 6.6.0 - 2022-10-31
 --------------------------
 * Bug fixes (see mercurial logs for details)
diff --git a/modules/production/production.py b/modules/production/production.py
index df6a548396..baa749c385 100644
--- a/modules/production/production.py
+++ b/modules/production/production.py
@@ -779,12 +779,22 @@ class Production(ShipmentAssignMixin, Workflow, ModelSQL, ModelView):
     def assign_try(cls, productions):
         pool = Pool()
         Move = pool.get('stock.move')
-        if Move.assign_try(
-                [m for p in productions for m in p.assign_moves]):
+        to_assign = [
+            m for p in productions for m in p.assign_moves
+            if m.assignation_required]
+        if Move.assign_try(to_assign):
             cls.assign(productions)
-            return True
         else:
-            return False
+            to_assign = []
+            for production in productions:
+                if any(
+                        m.state in {'staging', 'draft'}
+                        for m in production.assign_moves
+                        if m.assignation_required):
+                    continue
+                to_assign.append(production)
+            if to_assign:
+                cls.assign(to_assign)
 
     @classmethod
     def _get_reschedule_domain(cls, date):
diff --git a/modules/production/tests/scenario_production.rst b/modules/production/tests/scenario_production.rst
index ba9e0e5ba8..fe23bae004 100644
--- a/modules/production/tests/scenario_production.rst
+++ b/modules/production/tests/scenario_production.rst
@@ -161,7 +161,8 @@ Test reset bom button::
 Do the production::
 
     >>> production.click('assign_try')
-    True
+    >>> production.state
+    'assigned'
     >>> all(i.state == 'assigned' for i in production.inputs)
     True
     >>> production.click('run')
@@ -192,7 +193,6 @@ Make a production with effective date yesterday and running the day before::
     >>> production.quantity = 2
     >>> production.click('wait')
     >>> production.click('assign_try')
-    True
     >>> production.click('run')
     >>> production.reload()
     >>> all(i.effective_date == before_yesterday for i in production.inputs)
diff --git a/modules/production_work/tests/scenario_production_work.rst b/modules/production_work/tests/scenario_production_work.rst
index 1021e084d5..a66f44ccaa 100644
--- a/modules/production_work/tests/scenario_production_work.rst
+++ b/modules/production_work/tests/scenario_production_work.rst
@@ -179,7 +179,6 @@ Test works::
 Run the production::
 
     >>> production.click('assign_try')
-    True
     >>> production.click('run')
     >>> production.state
     'running'
diff --git a/modules/purchase/tests/scenario_purchase.rst b/modules/purchase/tests/scenario_purchase.rst
index 0d991cc542..9e8bfa87b2 100644
--- a/modules/purchase/tests/scenario_purchase.rst
+++ b/modules/purchase/tests/scenario_purchase.rst
@@ -358,7 +358,6 @@ Check Return Shipments::
     >>> move_return.quantity
     4.0
     >>> ship_return.click('assign_try')
-    True
     >>> ship_return.click('done')
     >>> ship_return.state
     'done'
@@ -429,7 +428,6 @@ Checking Shipments::
 
     >>> mix_return.click('wait')
     >>> mix_return.click('assign_try')
-    True
     >>> mix_return.click('done')
     >>> move_return, = mix_return.moves
     >>> move_return.product.rec_name
@@ -497,7 +495,6 @@ Checking Shipments::
 
     >>> mix_return.click('wait')
     >>> mix_return.click('assign_try')
-    True
     >>> mix_return.click('done')
     >>> move_return, = mix_return.moves
     >>> move_return.product.rec_name
diff --git a/modules/sale/tests/scenario_sale.rst b/modules/sale/tests/scenario_sale.rst
index c13e9d2889..4b80bfbb4e 100644
--- a/modules/sale/tests/scenario_sale.rst
+++ b/modules/sale/tests/scenario_sale.rst
@@ -265,7 +265,6 @@ Not yet linked to invoice lines::
 Validate Shipments::
 
     >>> shipment.click('assign_try')
-    True
     >>> shipment.click('pick')
     >>> shipment.click('pack')
     >>> shipment.click('done')
@@ -365,7 +364,6 @@ Ship 3 products::
     4.0
     >>> stock_inventory_move.quantity = 3.0
     >>> shipment.click('assign_try')
-    True
     >>> shipment.click('pick')
     >>> shipment.click('pack')
     >>> shipment.click('done')
@@ -506,7 +504,6 @@ Checking Shipments::
     >>> move_return.quantity
     2.0
     >>> mix_shipment.click('assign_try')
-    True
     >>> mix_shipment.click('pick')
     >>> mix_shipment.click('pack')
     >>> mix_shipment.click('done')
@@ -568,7 +565,6 @@ Checking Shipments::
     >>> move_return.quantity
     3.0
     >>> mix_shipment.click('assign_try')
-    True
     >>> mix_shipment.click('pick')
     >>> mix_shipment.click('pack')
     >>> move_shipment, = mix_shipment.outgoing_moves
@@ -657,7 +653,6 @@ to invoices::
     >>> for move in shipment.inventory_moves:
     ...     move.quantity = 5.0
     >>> shipment.click('assign_try')
-    True
     >>> shipment.click('pick')
     >>> shipment.click('pack')
     >>> shipment.click('done')
diff --git a/modules/sale_advance_payment/tests/scenario_advance_payment.rst b/modules/sale_advance_payment/tests/scenario_advance_payment.rst
index 1b304255f0..ec853ec732 100644
--- a/modules/sale_advance_payment/tests/scenario_advance_payment.rst
+++ b/modules/sale_advance_payment/tests/scenario_advance_payment.rst
@@ -245,7 +245,6 @@ Let's try to pack it::
 
     >>> shipment.click('wait')
     >>> shipment.click('assign_try')
-    True
     >>> shipment.click('pick')
     >>> shipment.click('pack')  # doctest: +IGNORE_EXCEPTION_DETAIL
     Traceback (most recent call last):
diff --git a/modules/sale_shipment_grouping/tests/scenario_sale_shipment_grouping.rst b/modules/sale_shipment_grouping/tests/scenario_sale_shipment_grouping.rst
index 04bff28b0c..399375d9c0 100644
--- a/modules/sale_shipment_grouping/tests/scenario_sale_shipment_grouping.rst
+++ b/modules/sale_shipment_grouping/tests/scenario_sale_shipment_grouping.rst
@@ -147,7 +147,7 @@ Check the shipments::
     >>> len(shipments)
     2
     >>> for shipment in shipments:
-    ...     _ = shipment.click('assign_try')
+    ...     shipment.click('assign_try')
     ...     shipment.click('pick')
     ...     shipment.click('pack')
     ...     shipment.click('done')
diff --git a/modules/sale_supply/tests/scenario_sale_supply.rst b/modules/sale_supply/tests/scenario_sale_supply.rst
index cfdc63b9a4..feda03a5a5 100644
--- a/modules/sale_supply/tests/scenario_sale_supply.rst
+++ b/modules/sale_supply/tests/scenario_sale_supply.rst
@@ -243,7 +243,6 @@ not create a new purchase request::
     >>> inventory.state
     'done'
     >>> shipment.click('assign_try')
-    True
     >>> shipment.click('pick')
     >>> shipment.click('pack')
 
diff --git a/modules/stock/CHANGELOG b/modules/stock/CHANGELOG
index c177e4881a..7e44592fbf 100644
--- a/modules/stock/CHANGELOG
+++ b/modules/stock/CHANGELOG
@@ -1,3 +1,4 @@
+* Assign all possible shipments when trying
 * Store warehouse locations on shipments
 
 Version 6.6.0 - 2022-10-31
diff --git a/modules/stock/shipment.py b/modules/stock/shipment.py
index 136bfb825a..79e5bea871 100644
--- a/modules/stock/shipment.py
+++ b/modules/stock/shipment.py
@@ -977,7 +977,17 @@ class ShipmentInReturn(ShipmentAssignMixin, Workflow, ModelSQL, ModelView):
                 success = False
         if success:
             cls.assign(shipments)
-        return success
+        else:
+            to_assign = []
+            for shipment in shipments:
+                if any(
+                        m.state in {'staging', 'draft'}
+                        for m in shipment.assign_moves
+                        if m.assignation_required):
+                    continue
+                to_assign.append(shipment)
+            if to_assign:
+                cls.assign(to_assign)
 
     @classmethod
     def _get_reschedule_domain(cls, date):
@@ -1694,9 +1704,17 @@ class ShipmentOut(ShipmentAssignMixin, Workflow, ModelSQL, ModelView):
             if m.assignation_required]
         if Move.assign_try(to_assign):
             cls.assign(shipments)
-            return True
         else:
-            return False
+            to_assign = []
+            for shipment in shipments:
+                if any(
+                        m.state in {'staging', 'draft'}
+                        for m in shipment.assign_moves
+                        if m.assignation_required):
+                    continue
+                to_assign.append(shipment)
+            if to_assign:
+                cls.assign(to_assign)
 
     @classmethod
     def _get_reschedule_domain(cls, date):
@@ -2815,11 +2833,19 @@ class ShipmentInternal(ShipmentAssignMixin, Workflow, ModelSQL, ModelView):
         to_assign = [
             m for s in shipments for m in s.assign_moves
             if m.assignation_required]
-        if not to_assign or Move.assign_try(to_assign):
+        if Move.assign_try(to_assign):
             cls.assign(shipments)
-            return True
         else:
-            return False
+            to_assign = []
+            for shipment in shipments:
+                if any(
+                        m.state in {'staging', 'draft'}
+                        for m in shipment.assign_moves
+                        if m.assignation_required):
+                    continue
+                to_assign.append(shipment)
+            if to_assign:
+                cls.assign(to_assign)
 
     @property
     def _move_planned_date(self):
@@ -2912,7 +2938,8 @@ class Assign(Wizard):
     ignore = StateTransition()
 
     def transition_start(self):
-        if self.record.assign_try():
+        self.record.assign_try()
+        if self.record.state == 'assigned':
             return 'end'
         else:
             return 'partial'
diff --git a/modules/stock/tests/scenario_stock_reporting.rst b/modules/stock/tests/scenario_stock_reporting.rst
index 8863d2f8fe..fd9a1f285f 100644
--- a/modules/stock/tests/scenario_stock_reporting.rst
+++ b/modules/stock/tests/scenario_stock_reporting.rst
@@ -112,7 +112,6 @@ Add two shipment lines of same product and go through the workflow::
     >>> shipment_out.save()
     >>> shipment_out.click('wait')
     >>> shipment_out.click('assign_try')
-    True
     >>> shipment_out.click('pick')
     >>> shipment_out.click('pack')
     >>> shipment_out.click('done')
@@ -153,7 +152,6 @@ Create an internal shipment::
     >>> shipment_internal.save()
     >>> shipment_internal.click('wait')
     >>> shipment_internal.click('assign_try')
-    True
     >>> shipment_internal.click('done')
 
 Testing the report::
diff --git a/modules/stock/tests/scenario_stock_shipment_internal.rst b/modules/stock/tests/scenario_stock_shipment_internal.rst
index b0a0ff38ae..a678ff6cfc 100644
--- a/modules/stock/tests/scenario_stock_shipment_internal.rst
+++ b/modules/stock/tests/scenario_stock_shipment_internal.rst
@@ -89,7 +89,8 @@ Create Internal Shipment::
     >>> shipment.state
     'waiting'
     >>> shipment.click('assign_try')
-    False
+    >>> shipment.state
+    'waiting'
     >>> shipment.assigned_by
     >>> shipment.done_by
 
@@ -110,7 +111,6 @@ Create Internal Shipment from lost_found location::
     >>> move.currency = company.currency
     >>> lost_found_shipment.click('wait')
     >>> lost_found_shipment.click('assign_try')
-    True
     >>> lost_found_shipment.state
     'assigned'
     >>> lost_found_shipment.click('done')
@@ -120,7 +120,6 @@ Create Internal Shipment from lost_found location::
 Check that now we can finish the older shipment::
 
     >>> shipment.click('assign_try')
-    True
     >>> shipment.assigned_by == employee
     True
     >>> shipment.done_by
diff --git a/modules/stock/tests/scenario_stock_shipment_out.rst b/modules/stock/tests/scenario_stock_shipment_out.rst
index 963b3d2b99..bc37fd238a 100644
--- a/modules/stock/tests/scenario_stock_shipment_out.rst
+++ b/modules/stock/tests/scenario_stock_shipment_out.rst
@@ -248,7 +248,6 @@ Make 1 unit of the product available::
 Finish the shipment::
 
     >>> shipment_out.click('assign_try')
-    True
     >>> shipment_out.click('pick')
     >>> shipment_out.click('pack')
     >>> shipment_out.click('done')
diff --git a/modules/stock_consignment/tests/scenario_stock_consignment.rst b/modules/stock_consignment/tests/scenario_stock_consignment.rst
index b70c8f61a9..5d8be93d75 100644
--- a/modules/stock_consignment/tests/scenario_stock_consignment.rst
+++ b/modules/stock_consignment/tests/scenario_stock_consignment.rst
@@ -121,7 +121,6 @@ Fill supplier consignment location::
     >>> shipment.state
     'waiting'
     >>> shipment.click('assign_try')
-    True
     >>> shipment.state
     'assigned'
     >>> shipment.click('done')
@@ -142,7 +141,6 @@ Use supplier consignment stock::
     >>> shipment.state
     'waiting'
     >>> shipment.click('assign_try')
-    True
     >>> shipment.state
     'assigned'
     >>> shipment.click('done')
@@ -184,7 +182,8 @@ Use supplier consignment stock for shipment out::
     >>> move, = shipment_out.inventory_moves
     >>> move.from_location = supplier_consignment_loc
     >>> shipment_out.click('assign_try')
-    True
+    >>> shipment_out.state
+    'assigned'
     >>> move, = shipment_out.inventory_moves
     >>> len(move.invoice_lines)
     1
@@ -203,7 +202,6 @@ Fill customer consignment location::
     >>> shipment.state
     'waiting'
     >>> shipment.click('assign_try')
-    True
     >>> shipment.state
     'assigned'
     >>> shipment.click('done')
@@ -224,7 +222,6 @@ Use customer consignment stock::
     >>> shipment.state
     'waiting'
     >>> shipment.click('assign_try')
-    True
     >>> shipment.state
     'assigned'
     >>> shipment.click('done')
@@ -268,7 +265,6 @@ Cancel supplier consignment stock::
     >>> shipment.state
     'waiting'
     >>> shipment.click('assign_try')
-    True
     >>> shipment.state
     'assigned'
     >>> move, = shipment.moves
diff --git a/modules/stock_consignment/tests/scenario_stock_consignment_supplier_customer.rst b/modules/stock_consignment/tests/scenario_stock_consignment_supplier_customer.rst
index f6b4abc3bf..e2d504e568 100644
--- a/modules/stock_consignment/tests/scenario_stock_consignment_supplier_customer.rst
+++ b/modules/stock_consignment/tests/scenario_stock_consignment_supplier_customer.rst
@@ -112,7 +112,6 @@ Fill supplier consignment location::
     >>> shipment.state
     'waiting'
     >>> shipment.click('assign_try')
-    True
     >>> shipment.state
     'assigned'
     >>> shipment.click('done')
@@ -133,7 +132,6 @@ Use supplier consignment stock by customer::
     >>> shipment.state
     'waiting'
     >>> shipment.click('assign_try')
-    True
     >>> shipment.state
     'assigned'
     >>> shipment.click('done')
diff --git a/modules/stock_location_move/tests/scenario_stock_location_move.rst b/modules/stock_location_move/tests/scenario_stock_location_move.rst
index 328b1c1933..942d11ebd3 100644
--- a/modules/stock_location_move/tests/scenario_stock_location_move.rst
+++ b/modules/stock_location_move/tests/scenario_stock_location_move.rst
@@ -43,7 +43,6 @@ Move pallet from storage1 to storage2::
     >>> shipment.click('wait')
 
     >>> shipment.click('assign_try')
-    True
     >>> shipment.state
     'assigned'
     >>> pallet.reload()
@@ -87,7 +86,8 @@ Concurrently move pallet::
     >>> shipment2.click('wait')
 
     >>> shipment1.click('assign_try')
-    True
+    >>> shipment1.state
+    'assigned'
     >>> shipment2.click('assign_try')  # doctest: +IGNORE_EXCEPTION_DETAIL
     Traceback (most recent call last):
         ...
@@ -117,7 +117,6 @@ Move pallet from storage1 to storage2 with lead_time::
     >>> shipment.locations.append(Location(pallet.id))
     >>> shipment.click('wait')
     >>> shipment.click('assign_try')
-    True
 
     >>> shipment.click('ship')
     >>> pallet.reload()
diff --git a/modules/stock_location_move/tests/scenario_stock_location_move_empty.rst b/modules/stock_location_move/tests/scenario_stock_location_move_empty.rst
index 43255f00aa..9fcbdd75e3 100644
--- a/modules/stock_location_move/tests/scenario_stock_location_move_empty.rst
+++ b/modules/stock_location_move/tests/scenario_stock_location_move_empty.rst
@@ -133,7 +133,6 @@ Ship 1 product from the locations::
     >>> move.to_location = customer_loc
     >>> shipment.click('wait')
     >>> shipment.click('assign_try')
-    True
     >>> shipment.click('pick')
     >>> shipment.click('pack')
     >>> shipment.click('done')
diff --git a/modules/stock_lot/tests/scenario_stock_lot_assign_try.rst b/modules/stock_lot/tests/scenario_stock_lot_assign_try.rst
index f080c9b405..42f8df6a3f 100644
--- a/modules/stock_lot/tests/scenario_stock_lot_assign_try.rst
+++ b/modules/stock_lot/tests/scenario_stock_lot_assign_try.rst
@@ -115,7 +115,6 @@ Request specific lot in stock assignation::
 Assign the shipment::
 
     >>> shipment.click('assign_try')
-    True
     >>> shipment.state
     'assigned'
     >>> move, = shipment.inventory_moves
diff --git a/modules/stock_lot_unit/tests/scenario_stock_lot_unit.rst b/modules/stock_lot_unit/tests/scenario_stock_lot_unit.rst
index 5cc30c64d0..0d340e0682 100644
--- a/modules/stock_lot_unit/tests/scenario_stock_lot_unit.rst
+++ b/modules/stock_lot_unit/tests/scenario_stock_lot_unit.rst
@@ -100,7 +100,6 @@ Let's ship a product with a lot::
     >>> move.to_location = customer_loc
     >>> shipment.click('wait')
     >>> shipment.click('assign_try')
-    True
     >>> move.lot = lot
     >>> shipment.click('pick')
     >>> shipment.click('pack')
@@ -129,7 +128,6 @@ Let's ship now two times the same lot::
     >>> move2.to_location = customer_loc
     >>> shipment.click('wait')
     >>> shipment.click('assign_try')
-    True
     >>> move1, move2 = shipment.inventory_moves
     >>> move1.lot = lot
     >>> move2.lot = lot
@@ -156,7 +154,6 @@ Now let's ship one move with a quantity bigger than lot unit quantity::
     >>> move.to_location = customer_loc
     >>> shipment.click('wait')
     >>> shipment.click('assign_try')
-    True
     >>> move, = shipment.inventory_moves
     >>> move.lot = lot
     >>> shipment.click('pick')  # doctest: +IGNORE_EXCEPTION_DETAIL
diff --git a/modules/stock_package_shipping_dpd/tests/scenario_shipping_dpd.rst b/modules/stock_package_shipping_dpd/tests/scenario_shipping_dpd.rst
index 5199beffc9..8bf00502d2 100644
--- a/modules/stock_package_shipping_dpd/tests/scenario_shipping_dpd.rst
+++ b/modules/stock_package_shipping_dpd/tests/scenario_shipping_dpd.rst
@@ -203,7 +203,6 @@ Create the packs and ship the shipment::
     >>> Package = Model.get('stock.package')
     >>> shipment, = sale.shipments
     >>> shipment.click('assign_try')
-    True
     >>> shipment.click('pick')
     >>> pack = shipment.packages.new()
     >>> pack.type = box
diff --git a/modules/stock_package_shipping_ups/tests/scenario_shipping_ups.rst b/modules/stock_package_shipping_ups/tests/scenario_shipping_ups.rst
index a5f39992ed..eabd8a0c07 100644
--- a/modules/stock_package_shipping_ups/tests/scenario_shipping_ups.rst
+++ b/modules/stock_package_shipping_ups/tests/scenario_shipping_ups.rst
@@ -210,7 +210,6 @@ Create the packs and ship the shipment::
     >>> shipment, = sale.shipments
     >>> shipment.shipping_description = 'Football Players'
     >>> shipment.click('assign_try')
-    True
     >>> shipment.click('pick')
     >>> pack = shipment.packages.new()
     >>> pack.type = ups_box