diff --git a/src/CONST/index.ts b/src/CONST/index.ts
index 9103648114bb..7a58d40ae4cd 100644
--- a/src/CONST/index.ts
+++ b/src/CONST/index.ts
@@ -8192,6 +8192,8 @@ const CONST = {
         GPS_TOOLTIP: 'gpsTooltip',
         HAS_FILTER_NEGATION: 'hasFilterNegation',
         MILEAGE_RATE_AUTO_UPDATED: 'mileageRateAutoUpdated',
+        REQUIRE_FIELDS_RULE_RECEIPT_COUPLING_TOOLTIP: 'requireFieldsRuleReceiptCouplingTooltip',
+        REQUIRE_FIELDS_RULE_ITEMIZED_RECEIPT_COUPLING_TOOLTIP: 'requireFieldsRuleItemizedReceiptCouplingTooltip',
     },
     CHANGE_POLICY_TRAINING_MODAL: 'changePolicyModal',
     AGENTS_RULES_BANNER: 'agentsRulesBanner',
diff --git a/src/components/ProductTrainingContext/TOOLTIPS.ts b/src/components/ProductTrainingContext/TOOLTIPS.ts
index 73d19b027ad0..05fca9e89df3 100644
--- a/src/components/ProductTrainingContext/TOOLTIPS.ts
+++ b/src/components/ProductTrainingContext/TOOLTIPS.ts
@@ -8,7 +8,12 @@ import type {ValueOf} from 'type-fest';
 const {CONCIERGE_LHN_GBR, OUTSTANDING_FILTER, ACCOUNT_SWITCHER, SCAN_TEST_DRIVE_CONFIRMATION, GPS_TOOLTIP, HAS_FILTER_NEGATION, MILEAGE_RATE_AUTO_UPDATED} =
     CONST.PRODUCT_TRAINING_TOOLTIP_NAMES;
 
-type ProductTrainingTooltipName = Exclude<ValueOf<typeof CONST.PRODUCT_TRAINING_TOOLTIP_NAMES>, typeof CONST.PRODUCT_TRAINING_TOOLTIP_NAMES.MULTI_SCAN_EDUCATIONAL_MODAL>;
+type ProductTrainingTooltipName = Exclude<
+    ValueOf<typeof CONST.PRODUCT_TRAINING_TOOLTIP_NAMES>,
+    | typeof CONST.PRODUCT_TRAINING_TOOLTIP_NAMES.MULTI_SCAN_EDUCATIONAL_MODAL
+    | typeof CONST.PRODUCT_TRAINING_TOOLTIP_NAMES.REQUIRE_FIELDS_RULE_RECEIPT_COUPLING_TOOLTIP
+    | typeof CONST.PRODUCT_TRAINING_TOOLTIP_NAMES.REQUIRE_FIELDS_RULE_ITEMIZED_RECEIPT_COUPLING_TOOLTIP
+>;
 
 type ShouldShowConditionProps = {
     shouldUseNarrowLayout: boolean;
diff --git a/src/components/RequireFieldsRules/FieldRequirementSettingRow.tsx b/src/components/RequireFieldsRules/FieldRequirementSettingRow.tsx
index e36f68b87c23..bd5f8e258eb2 100644
--- a/src/components/RequireFieldsRules/FieldRequirementSettingRow.tsx
+++ b/src/components/RequireFieldsRules/FieldRequirementSettingRow.tsx
@@ -5,19 +5,29 @@ import EducationalTooltip from '@components/Tooltip/EducationalTooltip';
 
 import {useMemoizedLazyExpensifyIcons} from '@hooks/useLazyAsset';
 import useLocalize from '@hooks/useLocalize';
+import useOnyx from '@hooks/useOnyx';
 import useTheme from '@hooks/useTheme';
 import useThemeStyles from '@hooks/useThemeStyles';
 
-import {getRequireFieldsFieldCouplingTooltipKey, isRequireFieldsFieldCouplingDisabled} from '@libs/RequireFieldsRulesUtils';
+import {dismissProductTraining} from '@libs/actions/Welcome';
+import {
+    canClearRequireFieldsField,
+    getRequireFieldsFieldCouplingTooltipKey,
+    isRequireFieldsFieldCouplingDisabled,
+    REQUIRE_FIELDS_COUPLING_TOOLTIP_NAMES,
+} from '@libs/RequireFieldsRulesUtils';
 import type {FieldRequirementsDirection} from '@libs/RequireFieldsRulesUtils';
+import isProductTrainingElementDismissed from '@libs/TooltipUtils';
 
 import variables from '@styles/variables';
 
 import CONST from '@src/CONST';
+import ONYXKEYS from '@src/ONYXKEYS';
 import type {RequireFieldsRuleForm, RequireFieldsRuleSettingFieldKey} from '@src/types/form/RequireFieldsRuleForm';
 import type {PolicyCategory} from '@src/types/onyx';
+import isLoadingOnyxValue from '@src/types/utils/isLoadingOnyxValue';
 
-import React, {useCallback, useState} from 'react';
+import React, {useCallback} from 'react';
 import {View} from 'react-native';
 
 import FieldRequirementsDirectionToggle from './FieldRequirementsDirectionToggle';
@@ -54,16 +64,29 @@ function FieldRequirementSettingRow({
     const theme = useTheme();
     const {translate} = useLocalize();
     const expensifyIcons = useMemoizedLazyExpensifyIcons(['Close', 'Lightbulb']);
-    const [dismissedCouplingTooltipKey, setDismissedCouplingTooltipKey] = useState<string | undefined>();
+    const [dismissedProductTraining, dismissedProductTrainingMetadata] = useOnyx(ONYXKEYS.NVP_DISMISSED_PRODUCT_TRAINING);
 
     const isCouplingDisabled = isRequireFieldsFieldCouplingDisabled(fieldKey, effectiveForm, category, touchedFields, isEditing, clearedFields);
     const couplingTooltipKey = getRequireFieldsFieldCouplingTooltipKey(fieldKey, effectiveForm, category, touchedFields, isEditing, clearedFields, couplingInteractionFields);
     const couplingTooltip = couplingTooltipKey ? translate(`workspace.rules.requireFieldsRule.${couplingTooltipKey}`) : undefined;
-    const shouldDisplayCouplingTooltip = !!couplingTooltip && dismissedCouplingTooltipKey !== couplingTooltipKey;
-
-    const hideCouplingTooltip = useCallback(() => {
-        setDismissedCouplingTooltipKey(couplingTooltipKey);
-    }, [couplingTooltipKey]);
+    const couplingTooltipName = couplingTooltipKey ? REQUIRE_FIELDS_COUPLING_TOOLTIP_NAMES[couplingTooltipKey] : undefined;
+    // Wait for the NVP so an already-dismissed tooltip doesn't flash before the dismissal arrives.
+    const shouldDisplayCouplingTooltip =
+        !!couplingTooltip &&
+        !!couplingTooltipName &&
+        !isLoadingOnyxValue(dismissedProductTrainingMetadata) &&
+        !isProductTrainingElementDismissed(couplingTooltipName, dismissedProductTraining);
+
+    const hideCouplingTooltip = useCallback(
+        (isDismissedUsingCloseButton = false) => {
+            if (!couplingTooltipName) {
+                return;
+            }
+
+            dismissProductTraining(couplingTooltipName, isDismissedUsingCloseButton);
+        },
+        [couplingTooltipName],
+    );
 
     const renderCouplingTooltipContent = useCallback(() => {
         return (
@@ -83,7 +106,7 @@ function FieldRequirementSettingRow({
                         shouldUseAutoHitSlop
                         accessibilityLabel={translate('common.noThanks')}
                         role={CONST.ROLE.BUTTON}
-                        onPress={hideCouplingTooltip}
+                        onPress={() => hideCouplingTooltip(true)}
                     >
                         <Icon
                             src={expensifyIcons.Close}
@@ -128,6 +151,7 @@ function FieldRequirementSettingRow({
             <FieldRequirementsDirectionToggle
                 direction={setting}
                 disabled={!canWriteRules || isCouplingDisabled}
+                canDeselect={canClearRequireFieldsField(fieldKey)}
                 onSelect={handleSelectSetting}
             />
         </View>
@@ -146,7 +170,7 @@ function FieldRequirementSettingRow({
             anchorAlignment={{horizontal: CONST.MODAL.ANCHOR_ORIGIN_HORIZONTAL.LEFT, vertical: CONST.MODAL.ANCHOR_ORIGIN_VERTICAL.BOTTOM}}
             shiftHorizontal={variables.mileageRateTooltipShiftHorizontal}
             shiftVertical={variables.mileageRateTooltipShiftVertical}
-            onTooltipPress={hideCouplingTooltip}
+            onTooltipPress={() => hideCouplingTooltip()}
             shouldHideOnScroll
         >
             {rowContent}
diff --git a/src/components/RequireFieldsRules/FieldRequirementsDirectionToggle.tsx b/src/components/RequireFieldsRules/FieldRequirementsDirectionToggle.tsx
index aba4b6b78dd9..e1b55722012d 100644
--- a/src/components/RequireFieldsRules/FieldRequirementsDirectionToggle.tsx
+++ b/src/components/RequireFieldsRules/FieldRequirementsDirectionToggle.tsx
@@ -13,20 +13,36 @@ import {View} from 'react-native';
 type FieldRequirementsDirectionToggleProps = {
     direction?: FieldRequirementsDirection;
     disabled?: boolean;
+
+    /** When false, pressing the selected direction does nothing instead of clearing it. */
+    canDeselect?: boolean;
     onSelect: (direction: FieldRequirementsDirection | undefined) => void;
 };
 
-function FieldRequirementsDirectionToggle({direction, disabled = false, onSelect}: FieldRequirementsDirectionToggleProps) {
+function FieldRequirementsDirectionToggle({direction, disabled = false, canDeselect = true, onSelect}: FieldRequirementsDirectionToggleProps) {
     const styles = useThemeStyles();
     const {translate} = useLocalize();
 
     const isRequireSelected = direction === CONST.FIELD_REQUIREMENTS_DIRECTION.REQUIRE;
     const isWaiveDirectionSelected = direction === CONST.FIELD_REQUIREMENTS_DIRECTION.DO_NOT_REQUIRE;
 
+    const selectDirection = (isSelected: boolean, nextDirection: FieldRequirementsDirection) => {
+        if (!isSelected) {
+            onSelect(nextDirection);
+            return;
+        }
+
+        if (!canDeselect) {
+            return;
+        }
+
+        onSelect(undefined);
+    };
+
     return (
         <View style={[styles.flexRow, styles.border, styles.borderRadiusNormal]}>
             <Button
-                onPress={() => onSelect(isRequireSelected ? undefined : CONST.FIELD_REQUIREMENTS_DIRECTION.REQUIRE)}
+                onPress={() => selectDirection(isRequireSelected, CONST.FIELD_REQUIREMENTS_DIRECTION.REQUIRE)}
                 isDisabled={disabled}
                 size={CONST.BUTTON_SIZE.SMALL}
                 style={styles.ph0}
@@ -39,7 +55,7 @@ function FieldRequirementsDirectionToggle({direction, disabled = false, onSelect
                 </Button.Text>
             </Button>
             <Button
-                onPress={() => onSelect(isWaiveDirectionSelected ? undefined : CONST.FIELD_REQUIREMENTS_DIRECTION.DO_NOT_REQUIRE)}
+                onPress={() => selectDirection(isWaiveDirectionSelected, CONST.FIELD_REQUIREMENTS_DIRECTION.DO_NOT_REQUIRE)}
                 isDisabled={disabled}
                 size={CONST.BUTTON_SIZE.SMALL}
                 style={styles.ph0}
diff --git a/src/libs/RequireFieldsRulesUtils.ts b/src/libs/RequireFieldsRulesUtils.ts
index 1f7401963a60..f8e9dd5a1952 100644
--- a/src/libs/RequireFieldsRulesUtils.ts
+++ b/src/libs/RequireFieldsRulesUtils.ts
@@ -13,6 +13,8 @@ import type {Policy, PolicyCategories, PolicyCategory} from '@src/types/onyx';
 import type {PendingAction} from '@src/types/onyx/OnyxCommon';
 import type DeepValueOf from '@src/types/utils/DeepValueOf';
 
+import type {ValueOf} from 'type-fest';
+
 import {
     removePolicyCategoryItemizedReceiptsRequired,
     removePolicyCategoryReceiptsRequired,
@@ -839,6 +841,15 @@ type RequireFieldsDisplayedSettingParams = {
     isEditing: boolean;
 };
 
+/**
+ * Description and Attendees are stored as booleans, so "Don't require" is indistinguishable from having no
+ * override and there is no third state to deselect back to. Receipt fields do have one — no override at all,
+ * meaning the policy-level receipt requirement still applies — so only those can be cleared.
+ */
+function canClearRequireFieldsField(fieldKey: RequireFieldsRuleSettingFieldKey): boolean {
+    return fieldKey === INPUT_IDS.RECEIPT_SETTING || fieldKey === INPUT_IDS.ITEMIZED_RECEIPT_SETTING;
+}
+
 function getRequireFieldsDisplayedSetting({
     fieldKey,
     category,
@@ -849,25 +860,35 @@ function getRequireFieldsDisplayedSetting({
     clearedFields,
     isEditing,
 }: RequireFieldsDisplayedSettingParams): FieldRequirementsDirection | undefined {
-    if (clearedFields?.has(fieldKey)) {
-        return undefined;
-    }
+    const displayedSetting = ((): FieldRequirementsDirection | undefined => {
+        if (clearedFields?.has(fieldKey)) {
+            return undefined;
+        }
 
-    if (touchedFields?.has(fieldKey)) {
-        return effectiveForm?.[fieldKey];
-    }
+        if (touchedFields?.has(fieldKey)) {
+            return effectiveForm?.[fieldKey];
+        }
 
-    // After changing category on edit, the draft holds the preserved rule settings and may
-    // remount without local touched state — read those explicit draft values directly.
-    if (isEditing && originalCategoryName && rawForm?.[INPUT_IDS.CATEGORY] && rawForm[INPUT_IDS.CATEGORY] !== originalCategoryName) {
-        return rawForm[fieldKey];
-    }
+        // After changing category on edit, the draft holds the preserved rule settings and may
+        // remount without local touched state — read those explicit draft values directly.
+        if (isEditing && originalCategoryName && rawForm?.[INPUT_IDS.CATEGORY] && rawForm[INPUT_IDS.CATEGORY] !== originalCategoryName) {
+            return rawForm[fieldKey];
+        }
 
-    if (isEditing) {
-        return getActiveFieldRequirementsDirection(category, fieldKey);
+        if (isEditing) {
+            return getActiveFieldRequirementsDirection(category, fieldKey);
+        }
+
+        return undefined;
+    })();
+
+    // A missing value on a boolean-backed field means Don't require, so show it selected rather than
+    // leaving the toggle blank. Receipt fields keep a blank state for "no override".
+    if (displayedSetting === undefined && !canClearRequireFieldsField(fieldKey)) {
+        return CONST.FIELD_REQUIREMENTS_DIRECTION.DO_NOT_REQUIRE;
     }
 
-    return undefined;
+    return displayedSetting;
 }
 
 /**
@@ -909,6 +930,15 @@ function isRequireFieldsFieldCouplingDisabled(
 
 type RequireFieldsFieldCouplingTooltipKey = 'receiptDisabledWhenItemizedRequired' | 'itemizedDisabledWhenReceiptWaived';
 
+/**
+ * Name this coupling tooltip is dismissed under in the dismissed-product-training NVP, so dismissing it once
+ * keeps it dismissed for later rules instead of only for the current mount.
+ */
+const REQUIRE_FIELDS_COUPLING_TOOLTIP_NAMES: Record<RequireFieldsFieldCouplingTooltipKey, ValueOf<typeof CONST.PRODUCT_TRAINING_TOOLTIP_NAMES>> = {
+    receiptDisabledWhenItemizedRequired: CONST.PRODUCT_TRAINING_TOOLTIP_NAMES.REQUIRE_FIELDS_RULE_RECEIPT_COUPLING_TOOLTIP,
+    itemizedDisabledWhenReceiptWaived: CONST.PRODUCT_TRAINING_TOOLTIP_NAMES.REQUIRE_FIELDS_RULE_ITEMIZED_RECEIPT_COUPLING_TOOLTIP,
+};
+
 function getRequireFieldsFieldCouplingTooltipKey(
     fieldKey: RequireFieldsRuleSettingFieldKey,
     effectiveForm: RequireFieldsRuleForm | undefined,
@@ -939,8 +969,10 @@ function getRequireFieldsFieldCouplingTooltipKey(
 }
 
 export {
+    canClearRequireFieldsField,
     categoryHasAnyRequireFieldsRule,
     deleteRequireFieldsRule,
+    REQUIRE_FIELDS_COUPLING_TOOLTIP_NAMES,
     formatRequireFieldsRuleDescriptions,
     getActiveFieldRequirementsDirection,
     getEffectiveRequireFieldsRuleForm,
diff --git a/src/pages/workspace/rules/RequireFieldsRules/RequireFieldsRuleCategoryPageBase.tsx b/src/pages/workspace/rules/RequireFieldsRules/RequireFieldsRuleCategoryPageBase.tsx
index 8b6f8a242e05..e12e14cb351a 100644
--- a/src/pages/workspace/rules/RequireFieldsRules/RequireFieldsRuleCategoryPageBase.tsx
+++ b/src/pages/workspace/rules/RequireFieldsRules/RequireFieldsRuleCategoryPageBase.tsx
@@ -91,8 +91,9 @@ function RequireFieldsRuleCategoryPageBase({policyID, categoryName}: RequireFiel
 
         for (const fieldKey of SETTING_FIELD_KEYS) {
             if (isEditing) {
-                // Edit drafts are seeded with DO_NOT_REQUIRE for inactive fields. Only carry over
-                // settings that are actually selected in the UI (active category overrides).
+                // Carry over whatever the row currently shows. Description and Attendees are boolean-backed,
+                // so they always resolve to a direction (Don't require when there is no override) and are
+                // always carried; the receipt fields keep their blank "no override" state and are skipped.
                 const displayedSetting = getRequireFieldsDisplayedSetting({
                     fieldKey,
                     category: selectedCategory,
diff --git a/src/types/onyx/DismissedProductTraining.ts b/src/types/onyx/DismissedProductTraining.ts
index b4ad37155251..0967dcf8691a 100644
--- a/src/types/onyx/DismissedProductTraining.ts
+++ b/src/types/onyx/DismissedProductTraining.ts
@@ -1,7 +1,17 @@
 import CONST from '@src/CONST';
 
-const {CONCIERGE_LHN_GBR, OUTSTANDING_FILTER, ACCOUNT_SWITCHER, SCAN_TEST_DRIVE_CONFIRMATION, MULTI_SCAN_EDUCATIONAL_MODAL, GPS_TOOLTIP, HAS_FILTER_NEGATION, MILEAGE_RATE_AUTO_UPDATED} =
-    CONST.PRODUCT_TRAINING_TOOLTIP_NAMES;
+const {
+    CONCIERGE_LHN_GBR,
+    OUTSTANDING_FILTER,
+    ACCOUNT_SWITCHER,
+    SCAN_TEST_DRIVE_CONFIRMATION,
+    MULTI_SCAN_EDUCATIONAL_MODAL,
+    GPS_TOOLTIP,
+    HAS_FILTER_NEGATION,
+    MILEAGE_RATE_AUTO_UPDATED,
+    REQUIRE_FIELDS_RULE_RECEIPT_COUPLING_TOOLTIP,
+    REQUIRE_FIELDS_RULE_ITEMIZED_RECEIPT_COUPLING_TOOLTIP,
+} = CONST.PRODUCT_TRAINING_TOOLTIP_NAMES;
 
 /**
  * This type is used to store the timestamp of when the user dismisses a product training ui elements.
@@ -78,6 +88,18 @@ type DismissedProductTraining = {
      * When user dismisses the mileage rate auto-updated tooltip, we store the timestamp here.
      */
     [MILEAGE_RATE_AUTO_UPDATED]: DismissedProductTrainingElement;
+
+    /**
+     * When user dismisses the require fields rule tooltip explaining why Receipt is locked while
+     * Itemized receipt is required, we store the timestamp here.
+     */
+    [REQUIRE_FIELDS_RULE_RECEIPT_COUPLING_TOOLTIP]: DismissedProductTrainingElement;
+
+    /**
+     * When user dismisses the require fields rule tooltip explaining why Itemized receipt is locked
+     * while Receipt is waived, we store the timestamp here.
+     */
+    [REQUIRE_FIELDS_RULE_ITEMIZED_RECEIPT_COUPLING_TOOLTIP]: DismissedProductTrainingElement;
 };
 
 export default DismissedProductTraining;