diff --git a/CHANGELOG.md b/CHANGELOG.md
index 4e0063dec6c..6f0f409ca3a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -41,6 +41,7 @@ Note that this project **does not** adhere to [Semantic Versioning](https://semv
 - We fixed an issue where imports to a custom group would only work for the first entry [#11085](https://github.com/JabRef/jabref/issues/11085), [#11269](https://github.com/JabRef/jabref/issues/11269)
 - We fixed an issue where a new entry was not added to the selected group [#8933](https://github.com/JabRef/jabref/issues/8933)
 - We fixed an issue where the horizontal position of the Entry Preview inside the entry editor was not remembered across restarts [#11281](https://github.com/JabRef/jabref/issues/11281)
+- We fixed an issue where the search index was not updated after linking PDF files. [#11317](https://github.com/JabRef/jabref/pull/11317)
 - We fixed an issue where the entry editor context menu was not shown correctly when JabRef is opened on a second, extended screen [#11323](https://github.com/JabRef/jabref/issues/11323), [#11174](https://github.com/JabRef/jabref/issues/11174)
 
 ### Removed
diff --git a/src/main/java/org/jabref/gui/LibraryTab.java b/src/main/java/org/jabref/gui/LibraryTab.java
index ff2c9e4ba20..a8414a90d59 100644
--- a/src/main/java/org/jabref/gui/LibraryTab.java
+++ b/src/main/java/org/jabref/gui/LibraryTab.java
@@ -308,6 +308,7 @@ private void setDatabaseContext(BibDatabaseContext bibDatabaseContext) {
         setupMainPanel();
         setupAutoCompletion();
 
+        this.getDatabase().registerListener(new IndexUpdateListener());
         this.getDatabase().registerListener(new EntriesRemovedListener());
 
         // ensure that at each addition of a new entry, the entry is added to the groups interface
@@ -1085,9 +1086,9 @@ public void listen(FieldChangedEvent fieldChangedEvent) {
                     List<LinkedFile> newFileList = FileFieldParser.parse(fieldChangedEvent.getNewValue());
 
                     List<LinkedFile> addedFiles = new ArrayList<>(newFileList);
-                    addedFiles.remove(oldFileList);
+                    addedFiles.removeAll(oldFileList);
                     List<LinkedFile> removedFiles = new ArrayList<>(oldFileList);
-                    removedFiles.remove(newFileList);
+                    removedFiles.removeAll(newFileList);
 
                     try {
                         PdfIndexer indexer = PdfIndexerManager.getIndexer(bibDatabaseContext, preferencesService.getFilePreferences());
diff --git a/src/main/java/org/jabref/model/database/BibDatabaseContext.java b/src/main/java/org/jabref/model/database/BibDatabaseContext.java
index f8d4c3dfdcf..058a238187d 100644
--- a/src/main/java/org/jabref/model/database/BibDatabaseContext.java
+++ b/src/main/java/org/jabref/model/database/BibDatabaseContext.java
@@ -255,8 +255,8 @@ public Path getFulltextIndexPath() {
         Path indexPath;
 
         if (getDatabasePath().isPresent()) {
-            Path databaseFileName = getDatabasePath().get().getFileName();
-            String fileName = BackupFileUtil.getUniqueFilePrefix(databaseFileName) + "--" + databaseFileName;
+            Path databasePath = getDatabasePath().get();
+            String fileName = BackupFileUtil.getUniqueFilePrefix(databasePath) + "--" + databasePath.getFileName();
             indexPath = appData.resolve(fileName);
             LOGGER.debug("Index path for {} is {}", getDatabasePath().get(), indexPath);
             return indexPath;