diff --git a/apps/red-ui/src/app/modules/file-preview/utils/sort-by-page-rotation.utils.ts b/apps/red-ui/src/app/modules/file-preview/utils/sort-by-page-rotation.utils.ts
index 4ccce0755..6a18812ac 100644
--- a/apps/red-ui/src/app/modules/file-preview/utils/sort-by-page-rotation.utils.ts
+++ b/apps/red-ui/src/app/modules/file-preview/utils/sort-by-page-rotation.utils.ts
@@ -1,6 +1,12 @@
 import { AnnotationWrapper } from '@models/file/annotation.wrapper';
 
 export const sortTopLeftToBottomRight = (a1: AnnotationWrapper, a2: AnnotationWrapper): number => {
+    const A = a1.y;
+    const B = a1.y - a1.height;
+    const median = (A + B) / 2;
+    if (median > a2.y - a2.height && median < a2.y) {
+        return a1.x < a2.x ? -1 : 1;
+    }
     if (a1.y > a2.y) {
         return -1;
     }
@@ -11,6 +17,12 @@ export const sortTopLeftToBottomRight = (a1: AnnotationWrapper, a2: AnnotationWr
 };
 
 export const sortBottomLeftToTopRight = (a1: AnnotationWrapper, a2: AnnotationWrapper): number => {
+    const A = a1.x;
+    const B = a1.x + a1.width;
+    const median = (A + B) / 2;
+    if (median < a2.x + a2.width && median > a2.x) {
+        return a1.y < a2.y ? -1 : 1;
+    }
     if (a1.x < a2.x) {
         return -1;
     }
@@ -21,6 +33,12 @@ export const sortBottomLeftToTopRight = (a1: AnnotationWrapper, a2: AnnotationWr
 };
 
 export const sortBottomRightToTopLeft = (a1: AnnotationWrapper, a2: AnnotationWrapper): number => {
+    const A = a1.y;
+    const B = a1.y + a1.height;
+    const median = (A + B) / 2;
+    if (median < a2.y + a2.height && median > a2.y) {
+        return a1.x > a2.x ? -1 : 1;
+    }
     if (a1.y < a2.y) {
         return -1;
     }
@@ -31,6 +49,12 @@ export const sortBottomRightToTopLeft = (a1: AnnotationWrapper, a2: AnnotationWr
 };
 
 export const sortTopRightToBottomLeft = (a1: AnnotationWrapper, a2: AnnotationWrapper): number => {
+    const A = a1.x;
+    const B = a1.x - a1.width;
+    const median = (A + B) / 2;
+    if (median > a2.x - a2.width && median < a2.x) {
+        return a1.y > a2.y ? -1 : 1;
+    }
     if (a1.x > a2.x) {
         return -1;
     }