diff --git a/redaction-service-v1/redaction-service-server-v1/src/main/java/com/iqser/red/service/redaction/v1/server/redaction/service/RedactionLogMergeService.java b/redaction-service-v1/redaction-service-server-v1/src/main/java/com/iqser/red/service/redaction/v1/server/redaction/service/RedactionLogMergeService.java
index 34e055ac..0d557362 100644
--- a/redaction-service-v1/redaction-service-server-v1/src/main/java/com/iqser/red/service/redaction/v1/server/redaction/service/RedactionLogMergeService.java
+++ b/redaction-service-v1/redaction-service-server-v1/src/main/java/com/iqser/red/service/redaction/v1/server/redaction/service/RedactionLogMergeService.java
@@ -54,8 +54,25 @@ public class RedactionLogMergeService {
         log.info("Merging Redaction log with manual redactions");
         if (manualRedactions != null) {
 
-            Set<String> idsToRemove = manualRedactions.getIdsToRemove().stream().map(BaseAnnotation::getAnnotationId).collect(Collectors.toSet());
-            manualRedactions.getEntriesToAdd().removeIf(m -> idsToRemove.contains(m.getAnnotationId()));
+            Map<String, OffsetDateTime> idsToRemove = manualRedactions.getIdsToRemove()
+                    .stream()
+                    .collect(Collectors.toMap(BaseAnnotation::getAnnotationId, BaseAnnotation::getRequestDate));
+
+            List<ManualRedactionEntry> entriesToRemove = new ArrayList<>();
+            Set<String> removesToRemove = new HashSet<>();
+
+            manualRedactions.getEntriesToAdd().forEach(m -> {
+                if (idsToRemove.containsKey(m.getAnnotationId()) && idsToRemove.get(m.getAnnotationId()).isAfter(m.getRequestDate())) {
+                    entriesToRemove.add(m);
+                } else if (idsToRemove.containsKey(m.getAnnotationId()) && idsToRemove.get(m.getAnnotationId()).isBefore(m.getRequestDate())) {
+                    removesToRemove.add(m.getAnnotationId());
+                }
+            });
+
+            log.debug("Will remove these manual redactions {}", entriesToRemove);
+            log.debug("Will remove these id removals {}", removesToRemove);
+            manualRedactions.getIdsToRemove().removeIf(r -> removesToRemove.contains(r.getAnnotationId()));
+            manualRedactions.getEntriesToAdd().removeAll(entriesToRemove);
 
             var manualRedactionLogEntries = addManualAddEntries(sectionGrid, manualRedactions.getEntriesToAdd(), manualRedactions.getComments(), colors, types);