diff --git a/src/main/java/org/jabref/gui/fieldeditors/LinkedFileViewModel.java b/src/main/java/org/jabref/gui/fieldeditors/LinkedFileViewModel.java
index 3ef40844f14..68da8aec6f5 100644
--- a/src/main/java/org/jabref/gui/fieldeditors/LinkedFileViewModel.java
+++ b/src/main/java/org/jabref/gui/fieldeditors/LinkedFileViewModel.java
@@ -9,6 +9,7 @@
 import java.util.Arrays;
 import java.util.List;
 import java.util.Optional;
+import java.util.function.BiPredicate;
 
 import javax.xml.transform.TransformerException;
 
@@ -44,6 +45,7 @@
 import org.jabref.model.entry.LinkedFile;
 import org.jabref.model.metadata.FilePreferences;
 import org.jabref.model.strings.StringUtil;
+import org.jabref.model.util.OptionalUtil;
 import org.jabref.preferences.JabRefPreferences;
 
 import org.slf4j.Logger;
@@ -267,6 +269,37 @@ public void moveToDefaultDirectory() {
         }
     }
 
+    /**
+     * Gets the filename for the current linked file and compares it to the new suggested filename.
+     * @return true if the suggested filename is same as current filename.
+     */
+    public boolean isGeneratedNameSameAsOriginal() {
+        Path file = Paths.get(this.linkedFile.getLink());
+        String currentFileName = file.getFileName().toString();
+        String suggestedFileName = this.linkedFileHandler.getSuggestedFileName();
+
+        return currentFileName.equals(suggestedFileName);
+    }
+
+    /**
+     * Compares suggested filepath of current linkedFile with existing filepath.
+     * @return true if suggested filepath is same as existing filepath.
+     */
+    public boolean isGeneratedPathSameAsOriginal() {
+        Optional<Path> newDir = databaseContext.getFirstExistingFileDir(filePreferences);
+
+        Optional<Path> currentDir = linkedFile.findIn(databaseContext, filePreferences);
+
+        BiPredicate<Path, Path> equality = (fileA, fileB) -> {
+            try {
+                return Files.isSameFile(fileA, fileB);
+            } catch (IOException e) {
+                return false;
+            }
+        };
+        return OptionalUtil.equals(newDir, currentDir, equality);
+    }
+
     public void moveToDefaultDirectoryAndRename() {
         moveToDefaultDirectory();
         rename();
diff --git a/src/main/java/org/jabref/gui/fieldeditors/LinkedFilesEditor.java b/src/main/java/org/jabref/gui/fieldeditors/LinkedFilesEditor.java
index b782ae80c61..a2f1f168fce 100644
--- a/src/main/java/org/jabref/gui/fieldeditors/LinkedFilesEditor.java
+++ b/src/main/java/org/jabref/gui/fieldeditors/LinkedFilesEditor.java
@@ -220,15 +220,15 @@ private ContextMenu createContextMenuForFile(LinkedFileViewModel linkedFile) {
 
         MenuItem renameFile = new MenuItem(Localization.lang("Rename file"));
         renameFile.setOnAction(event -> linkedFile.rename());
-        renameFile.setDisable(linkedFile.getFile().isOnlineLink());
+        renameFile.setDisable(linkedFile.getFile().isOnlineLink() || linkedFile.isGeneratedNameSameAsOriginal());
 
         MenuItem moveFile = new MenuItem(Localization.lang("Move file to file directory"));
         moveFile.setOnAction(event -> linkedFile.moveToDefaultDirectory());
-        moveFile.setDisable(linkedFile.getFile().isOnlineLink());
+        moveFile.setDisable(linkedFile.getFile().isOnlineLink() || linkedFile.isGeneratedPathSameAsOriginal());
 
         MenuItem renameAndMoveFile = new MenuItem(Localization.lang("Move file to file directory and rename file"));
         renameAndMoveFile.setOnAction(event -> linkedFile.moveToDefaultDirectoryAndRename());
-        renameAndMoveFile.setDisable(linkedFile.getFile().isOnlineLink());
+        renameAndMoveFile.setDisable(linkedFile.getFile().isOnlineLink() || linkedFile.isGeneratedPathSameAsOriginal());
 
         MenuItem deleteFile = new MenuItem(Localization.lang("Permanently delete local file"));
         deleteFile.setOnAction(event -> viewModel.deleteFile(linkedFile));
diff --git a/src/main/java/org/jabref/model/util/OptionalUtil.java b/src/main/java/org/jabref/model/util/OptionalUtil.java
index 6d127c4e5ce..90290f597b2 100644
--- a/src/main/java/org/jabref/model/util/OptionalUtil.java
+++ b/src/main/java/org/jabref/model/util/OptionalUtil.java
@@ -5,6 +5,7 @@
 import java.util.List;
 import java.util.Optional;
 import java.util.function.BiFunction;
+import java.util.function.BiPredicate;
 import java.util.function.Function;
 import java.util.function.Predicate;
 import java.util.stream.Collectors;
@@ -20,6 +21,18 @@ public static <T> List<T> toList(Optional<T> value) {
         }
     }
 
+    public static <T, U> boolean equals(Optional<T> left, Optional<U> right, BiPredicate<T, U> equality) {
+        if (!left.isPresent()) {
+            return !right.isPresent();
+        } else {
+            if (right.isPresent()) {
+                return equality.test(left.get(), right.get());
+            } else {
+                return false;
+            }
+        }
+    }
+
     /**
      * No longer needed in Java 9 where {@code Optional<T>.stream()} is added.
      */