diff --git a/lessonbuilder/tool/src/java/org/sakaiproject/lessonbuildertool/tool/beans/SimplePageBean.java b/lessonbuilder/tool/src/java/org/sakaiproject/lessonbuildertool/tool/beans/SimplePageBean.java
index 72a84732d491..3a9082eeed69 100644
--- a/lessonbuilder/tool/src/java/org/sakaiproject/lessonbuildertool/tool/beans/SimplePageBean.java
+++ b/lessonbuilder/tool/src/java/org/sakaiproject/lessonbuildertool/tool/beans/SimplePageBean.java
@@ -151,6 +151,8 @@
 import java.util.function.Predicate;
 import java.util.regex.Matcher;
 import java.util.regex.Pattern;
+import java.util.stream.Collectors;
+import java.util.stream.IntStream;
 
 /**
  * Backing bean for Simple pages
@@ -6738,6 +6740,28 @@ public void addMultimedia() {
 			if (!checkCsrf())
 			    return;
 
+			// For the sole case of adding multimedia as content links above another item
+			// (i.e., not the Add Content button at the top of the Lessons page, nor the Add Content '+'
+			// button at the bottom of a section), the items below the newly inserted content links
+			// need to have their sequence values revised, especially if there is more than one item to insert.
+			// First, collect these items in the itemsToFix list before inserting the new content links (which
+			// affects item sequencing for the page). After inserting the new content links, revise the sequence
+			// values for itemsToFix.
+			List<SimplePageItem> itemsToFix = null;
+			boolean fixItemSequence = StringUtils.isNotEmpty(addBefore) && !StringUtils.startsWith(addBefore, "-");
+			if (fixItemSequence) {
+				List<SimplePageItem> items = getItemsOnPage(getCurrentPageId());
+				items.sort(Comparator.comparing(SimplePageItem::getSequence));
+				long addBeforeItemId = Long.valueOf(addBefore);
+				int addBeforeIndex = IntStream.range(0, items.size())
+					.filter(i -> addBeforeItemId == items.get(i).getId())
+					.findFirst()
+					.orElse(-1);
+				if (addBeforeIndex >= 0) {
+					itemsToFix = items.stream().skip(addBeforeIndex).collect(Collectors.toList());
+				}
+			}
+
 			// SAK-41846 - Initialize counters to keep track of files to add and the item sequence values to adjust
 			totalMultimediaFilesToAdd = multipartMap.size();
 			remainingMultimediaFilesToAdd = totalMultimediaFilesToAdd;
@@ -6763,6 +6787,14 @@ public void addMultimedia() {
 					fileindex++;
 				}
 			}
+
+			if (fixItemSequence) {
+				for (SimplePageItem itemToFix : itemsToFix) {
+					itemToFix.setSequence(itemToFix.getSequence() + totalMultimediaFilesToAdd);
+					update(itemToFix);
+				}
+			}
+
 		} catch (Exception exception) {
 			log.error(exception.getMessage(), exception);
 		} finally {
@@ -6772,7 +6804,6 @@ public void addMultimedia() {
 			totalMultimediaFilesToAdd = 0;
 			remainingMultimediaFilesToAdd = 0;
 		}
-		
 	}
 
 	public void addMultimediaFile(MultipartFile file, String name){