diff --git a/addons/web/static/src/js/control_panel/custom_filter_item.js b/addons/web/static/src/js/control_panel/custom_filter_item.js
index 98080f6a418..b2d15746bb8 100644
--- a/addons/web/static/src/js/control_panel/custom_filter_item.js
+++ b/addons/web/static/src/js/control_panel/custom_filter_item.js
@@ -61,8 +61,8 @@ odoo.define('web.CustomFilterItem', function (require) {
             this.OPERATORS = FIELD_OPERATORS;
             this.FIELD_TYPES = FIELD_TYPES;
 
-            // Add default empty condition
-            this._addDefaultCondition();
+            // Add first condition
+            this._addNewCondition();
         }
 
         //---------------------------------------------------------------------
@@ -70,17 +70,20 @@ odoo.define('web.CustomFilterItem', function (require) {
         //---------------------------------------------------------------------
 
         /**
-         * Populate the conditions list with a default condition having as properties:
-         * - the first available field
-         * - the first available operator
+         * Populate the conditions list with a new condition having as properties:
+         * - the last condition or the first available field
+         * - the last condition or the first available operator
          * - a null or empty array value
          * @private
          */
-        _addDefaultCondition() {
-            const condition = {
-                field: 0,
-                operator: 0,
-            };
+        _addNewCondition() {
+            const lastCondition = [...this.state.conditions].pop();
+            const condition = lastCondition
+                ? Object.assign({}, lastCondition)
+                : {
+                    field: 0,
+                    operator: 0,
+                };
             this._setDefaultValue(condition);
             this.state.conditions.push(condition);
         }
@@ -185,7 +188,7 @@ odoo.define('web.CustomFilterItem', function (require) {
             // Reset state
             this.state.open = false;
             this.state.conditions = [];
-            this._addDefaultCondition();
+            this._addNewCondition();
         }
 
         /**
diff --git a/addons/web/static/src/xml/base.xml b/addons/web/static/src/xml/base.xml
index 25426728326..25099d03fa8 100644
--- a/addons/web/static/src/xml/base.xml
+++ b/addons/web/static/src/xml/base.xml
@@ -421,7 +421,7 @@
                 </button>
                 <button type="button"
                     class="btn btn-secondary o_add_condition"
-                    t-on-click="_addDefaultCondition"
+                    t-on-click="_addNewCondition"
                     >
                     <i class="fa fa-plus-circle"/>
                     <t>Add a condition</t>
diff --git a/addons/web/static/tests/control_panel/custom_filter_item_tests.js b/addons/web/static/tests/control_panel/custom_filter_item_tests.js
index 2fa4c5e4e57..05afe11d808 100644
--- a/addons/web/static/tests/control_panel/custom_filter_item_tests.js
+++ b/addons/web/static/tests/control_panel/custom_filter_item_tests.js
@@ -70,6 +70,48 @@ odoo.define('web.filter_menu_generator_tests', function (require) {
             cfi.destroy();
         });
 
+        QUnit.test('custom OR filter presets new condition from preceding', async function (assert) {
+            assert.expect(4);
+
+            const searchModel = new ActionModel();
+            const cfi = await createComponent(CustomFilterItem, {
+                props: {
+                    fields: this.fields,
+                },
+                env: { searchModel },
+            });
+
+            // Open custom filter form
+            await cpHelpers.toggleAddCustomFilter(cfi);
+
+            // Retrieve second selectable values for field and operator dropdowns
+            const fieldSecondValue = cfi.el.querySelector('.o_generator_menu_field option:nth-of-type(2)').value;
+            const operatorSecondValue = cfi.el.querySelector('.o_generator_menu_operator option:nth-of-type(2)').value;
+
+            // Check if they really exist…
+            assert.ok(!!fieldSecondValue);
+            assert.ok(!!operatorSecondValue);
+
+            // Add first filter condition
+            await testUtils.fields.editSelect(cfi.el.querySelector('.o_generator_menu_field'), fieldSecondValue);
+            await testUtils.fields.editSelect(cfi.el.querySelector('.o_generator_menu_operator'), operatorSecondValue);
+
+            // Add a second conditon on the filter being created
+            await cpHelpers.addCondition(cfi);
+
+            // Check the defaults for field and operator dropdowns
+            assert.strictEqual(
+                cfi.el.querySelector('.o_filter_condition:nth-of-type(2) .o_generator_menu_field').value,
+                fieldSecondValue
+            );
+            assert.strictEqual(
+                cfi.el.querySelector('.o_filter_condition:nth-of-type(2) .o_generator_menu_operator').value,
+                operatorSecondValue
+            );
+
+            cfi.destroy();
+        });
+
         QUnit.test('selection field: default and updated value', async function (assert) {
             assert.expect(4);
 
diff --git a/addons/web/static/tests/helpers/test_utils.js b/addons/web/static/tests/helpers/test_utils.js
index fb9654b52cf..f0f4977b15b 100644
--- a/addons/web/static/tests/helpers/test_utils.js
+++ b/addons/web/static/tests/helpers/test_utils.js
@@ -143,6 +143,7 @@ odoo.define('web.test_utils', async function (require) {
             toggleFilterMenu: testUtilsControlPanel.toggleFilterMenu,
             toggleAddCustomFilter: testUtilsControlPanel.toggleAddCustomFilter,
             applyFilter: testUtilsControlPanel.applyFilter,
+            addCondition: testUtilsControlPanel.addCondition,
             // GroupByMenu interactions
             toggleGroupByMenu: testUtilsControlPanel.toggleGroupByMenu,
             toggleAddCustomGroup: testUtilsControlPanel.toggleAddCustomGroup,
diff --git a/addons/web/static/tests/helpers/test_utils_control_panel.js b/addons/web/static/tests/helpers/test_utils_control_panel.js
index 2dda198017e..7270ee017df 100644
--- a/addons/web/static/tests/helpers/test_utils_control_panel.js
+++ b/addons/web/static/tests/helpers/test_utils_control_panel.js
@@ -104,6 +104,14 @@ odoo.define('web.test_utils_control_panel', function (require) {
         await click(getNode(el).querySelector(`div.o_add_filter_menu > button.o_apply_filter`));
     }
 
+    /**
+     * @param {EventTarget} el
+     * @returns {Promise}
+     */
+    async function addCondition(el) {
+        await click(getNode(el).querySelector(`div.o_add_filter_menu > button.o_add_condition`));
+    }
+
     /**
      * @param {EventTarget} el
      * @returns {Promise}
@@ -319,6 +327,7 @@ odoo.define('web.test_utils_control_panel', function (require) {
         toggleFilterMenu,
         toggleAddCustomFilter,
         applyFilter,
+        addCondition,
         // GroupByMenu interactions
         toggleGroupByMenu,
         toggleAddCustomGroup,