Index: oak-segment-tar/src/main/java/org/apache/jackrabbit/oak/segment/standby/client/StandbyDiff.java
===================================================================
--- oak-segment-tar/src/main/java/org/apache/jackrabbit/oak/segment/standby/client/StandbyDiff.java	(revision 1767067)
+++ oak-segment-tar/src/main/java/org/apache/jackrabbit/oak/segment/standby/client/StandbyDiff.java	(working copy)
@@ -183,7 +183,16 @@
 
     @Override
     public boolean childNodeChanged(String name, NodeState before, NodeState after) {
-        return process(name, "childNodeChanged", before, after);
+        try {
+            return process(name, "childNodeChanged", before, after);
+        } catch (RuntimeException e) {
+            log.trace("Check binaries for node {} and retry to process childNodeChanged", name);
+            // Attempt to load the binaries and retry, see OAK-4969
+            for (PropertyState propertyState : after.getProperties()) {
+                binaryCheck(propertyState);
+            }
+            return process(name, "childNodeChanged", before, after);
+        }
     }
 
     private boolean process(String name, String op, NodeState before, NodeState after) {
Index: oak-segment-tar/src/test/java/org/apache/jackrabbit/oak/segment/standby/DataStoreTestBase.java
===================================================================
--- oak-segment-tar/src/test/java/org/apache/jackrabbit/oak/segment/standby/DataStoreTestBase.java	(revision 1767067)
+++ oak-segment-tar/src/test/java/org/apache/jackrabbit/oak/segment/standby/DataStoreTestBase.java	(working copy)
@@ -101,7 +101,38 @@
         assertArrayEquals(data, testData);
     }
 
+    /**
+     * See OAK-4969
+     */
     @Test
+    public void testSyncUpdatedBinaryProperty() throws Exception {
+
+        final int mb = 1 * 1024 * 1024;
+        final int blobSize = 5 * mb;
+
+        FileStore primary = getPrimary();
+        FileStore secondary = getSecondary();
+
+        NodeStore store = SegmentNodeStoreBuilders.builder(primary).build();
+        try (
+                StandbyServerSync serverSync = new StandbyServerSync(getServerPort(), primary);
+                StandbyClientSync clientSync = newStandbyClientSync(secondary)
+        ) {
+            serverSync.start();
+
+            addTestContent(store, "server", blobSize);
+            primary.flush();
+            clientSync.run();
+            assertEquals(primary.getHead(), secondary.getHead());
+
+            addTestContent(store, "server", blobSize);
+            primary.flush();
+            clientSync.run();
+            assertEquals(primary.getHead(), secondary.getHead());
+        }
+    }
+
+    @Test
     public void testProxySkippedBytes() throws Exception {
         useProxy(100, 1, -1, false);
     }