diff --git a/apps/red-ui/src/app/modules/file-preview/components/pdf-viewer/pdf-viewer.component.ts b/apps/red-ui/src/app/modules/file-preview/components/pdf-viewer/pdf-viewer.component.ts
index 065f88ee5..388bc218f 100644
--- a/apps/red-ui/src/app/modules/file-preview/components/pdf-viewer/pdf-viewer.component.ts
+++ b/apps/red-ui/src/app/modules/file-preview/components/pdf-viewer/pdf-viewer.component.ts
@@ -194,9 +194,20 @@ export class PdfViewerComponent extends AutoUnsubscribe implements OnInit, OnCha
         await this._configureTextPopup();
 
         this.annotationManager.addEventListener('annotationSelected', async (annotations: Annotation[], action) => {
-            const nextAnnotations = this.multiSelectService.isEnabled ? this.annotationManager.getSelectedAnnotations() : annotations;
+            let nextAnnotations: Annotation[];
+
+            if (action === 'deselected') {
+                // Remove deselected annotations from selected list
+                nextAnnotations = this.annotationManager.getSelectedAnnotations().filter(ann => !annotations.find(a => a.Id === ann.Id));
+            } else if (!this.multiSelectService.isEnabled) {
+                // Only choose the last selected annotation, to bypass viewer multi select
+                nextAnnotations = annotations;
+            } else {
+                // Get selected annotations from the manager, no intervention needed
+                nextAnnotations = this.annotationManager.getSelectedAnnotations();
+            }
+
             this.annotationSelected.emit(nextAnnotations.map(ann => ann.Id));
-            this.annotationSelected.emit(action === 'selected' ? nextAnnotations.map(ann => ann.Id) : []);
             if (action === 'deselected') {
                 return this._toggleRectangleAnnotationAction(true);
             }