diff --git a/packages/rn-tester/js/examples/Playground/RNTesterPlayground.js b/packages/rn-tester/js/examples/Playground/RNTesterPlayground.js
index d37d0d4a9154..19990d64c08a 100644
--- a/packages/rn-tester/js/examples/Playground/RNTesterPlayground.js
+++ b/packages/rn-tester/js/examples/Playground/RNTesterPlayground.js
@@ -12,27 +12,111 @@ import type {RNTesterModuleExample} from '../../types/RNTesterTypes';
 
 import RNTesterText from '../../components/RNTesterText';
 import * as React from 'react';
-import {StyleSheet, View} from 'react-native';
+import {useState} from 'react';
+import {
+  Button,
+  SectionList,
+  StyleSheet,
+  Text,
+  View,
+} from 'react-native';
+
+const INITIAL_SECTIONS = [
+  {title: 'Section', data: [{key: 'a'}, {key: 'b'}, {key: 'c'}]},
+];
+const REORDERED_SECTIONS = [
+  {title: 'Section', data: [{key: 'b'}, {key: 'a'}, {key: 'c'}]},
+];
+
+function ItemSeparatorReproducer({leadingItem, trailingItem}: any) {
+  const leading = leadingItem?.key ?? 'undefined';
+  const trailing = trailingItem?.key ?? 'undefined';
+  return (
+    <View style={styles.separator}>
+      <Text style={styles.separatorText}>
+        leading: {leading} | trailing: {trailing}
+      </Text>
+    </View>
+  );
+}
+
+function ItemSeparatorComponentBugPlayground() {
+  const [sections, setSections] = useState(INITIAL_SECTIONS);
+  const [reordered, setReordered] = useState(false);
 
-function Playground() {
   return (
     <View style={styles.container}>
       <RNTesterText>
-        Edit "RNTesterPlayground.js" to change this file
+        Bug: ItemSeparatorComponent receives stale leadingItem/trailingItem after
+        reorder. Tap "Reorder" to swap first two items. The separator between
+        "b" and "a" should show "leading: b | trailing: a". If it shows
+        "leading: a | trailing: c" or "undefined", the bug is present.
       </RNTesterText>
+      <Button
+        title={reordered ? 'Reset' : 'Reorder (swap first two)'}
+        onPress={() => {
+          setReordered(r => !r);
+          setSections(reordered ? INITIAL_SECTIONS : REORDERED_SECTIONS);
+        }}
+      />
+      <SectionList
+        style={styles.list}
+        sections={sections}
+        keyExtractor={item => item.key}
+        renderItem={({item}) => (
+          <View style={styles.item}>
+            <Text>{item.key}</Text>
+          </View>
+        )}
+        renderSectionHeader={({section: {title}}) => (
+          <Text style={styles.sectionHeader}>{title}</Text>
+        )}
+        ItemSeparatorComponent={ItemSeparatorReproducer}
+      />
+    </View>
+  );
+}
+
+function Playground() {
+  return (
+    <View style={styles.container}>
+      <ItemSeparatorComponentBugPlayground />
     </View>
   );
 }
 
 const styles = StyleSheet.create({
   container: {
+    flex: 1,
     padding: 10,
   },
+  item: {
+    padding: 12,
+    backgroundColor: '#f0f0f0',
+  },
+  list: {
+    flex: 1,
+  },
+  sectionHeader: {
+    fontSize: 16,
+    fontWeight: 'bold',
+    paddingVertical: 8,
+  },
+  separator: {
+    height: 24,
+    backgroundColor: '#e0e0ff',
+    justifyContent: 'center',
+    paddingHorizontal: 8,
+  },
+  separatorText: {
+    fontSize: 12,
+  },
 });
 
 export default ({
   title: 'Playground',
   name: 'playground',
-  description: 'Test out new features and ideas.',
+  description:
+    'Test out new features and ideas. Includes reproducer for ItemSeparatorComponent leadingItem/trailingItem state bug.',
   render: (): React.Node => <Playground />,
 }: RNTesterModuleExample);
diff --git a/packages/virtualized-lists/Lists/__tests__/VirtualizedSectionList-test.js b/packages/virtualized-lists/Lists/__tests__/VirtualizedSectionList-test.js
index cc6b1da8d266..068c4560ef09 100644
--- a/packages/virtualized-lists/Lists/__tests__/VirtualizedSectionList-test.js
+++ b/packages/virtualized-lists/Lists/__tests__/VirtualizedSectionList-test.js
@@ -202,6 +202,64 @@ describe('VirtualizedSectionList', () => {
     expect(component).toMatchSnapshot();
   });
 
+  it('syncs ItemWithSeparator separator props when list re-renders with new leadingItem/trailingItem', async () => {
+    // Reproduces: When ItemWithSeparator re-renders with new props (e.g. after reorder),
+    // leadingItem/trailingItem can become stale (e.g. undefined when the row was previously at a boundary).
+    const separatorPropsReceived = [];
+    const ItemSeparatorWithCapture = props => {
+      separatorPropsReceived.push({
+        leadingItem: props.leadingItem?.key,
+        trailingItem: props.trailingItem?.key,
+      });
+      return <separator {...props} />;
+    };
+
+    let setSections;
+    const initialSections = [
+      {title: 's0', data: [{key: 'a'}, {key: 'b'}, {key: 'c'}]},
+    ];
+    const reorderedSections = [
+      {title: 's0', data: [{key: 'b'}, {key: 'a'}, {key: 'c'}]},
+    ];
+
+    function ListWithState() {
+      const [sections, setSectionsState] = React.useState(initialSections);
+      setSections = setSectionsState;
+      return (
+        <VirtualizedSectionList
+          ItemSeparatorComponent={ItemSeparatorWithCapture}
+          sections={sections}
+          renderItem={({item}) => <item title={item.key} />}
+          getItem={(data, index) => data[index]}
+          getItemCount={data => data.length}
+          keyExtractor={(item, index) => item.key}
+        />
+      );
+    }
+
+    let component;
+    await ReactTestRenderer.act(() => {
+      component = ReactTestRenderer.create(<ListWithState />);
+    });
+
+    separatorPropsReceived.length = 0;
+
+    await ReactTestRenderer.act(() => {
+      setSections(reorderedSections);
+    });
+
+    // After reorder: row "b" moved from index 1 to 0. Its trailing separator
+    // (between b and a) should show leadingItem: b, trailingItem: a.
+    // But buggy ItemWithSeparator keeps the initial
+    // state from when "b" was at index 1 (leadingItem: a, trailingItem: c), so
+    // the separator receives stale props and this assertion fails.
+    expect(separatorPropsReceived).toEqual(
+      expect.arrayContaining([
+        {leadingItem: 'b', trailingItem: 'a'},
+      ]),
+    );
+  });
+
   describe('scrollToLocation', () => {
     const ITEM_HEIGHT = 100;