diff --git a/CHANGELOG.md b/CHANGELOG.md
index 406e02ed7fe..b7db5173292 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -35,7 +35,7 @@ Note that this project **does not** adhere to [Semantic Versioning](http://semve
 - `log.txt` does not contain entries for non-found files during PDF indexing. [#9678](https://github.com/JabRef/jabref/pull/9678)
 - We improved the Medline importer to correctly import ISO dates for `revised`. [#9536](https://github.com/JabRef/jabref/issues/9536)
 - To avoid cluttering of the directory, We always delete the `.sav` file upon successful write. [#9675](https://github.com/JabRef/jabref/pull/9675)
-
+- We improved the unlinking/deletion of multiple linked files of an entry using the <kbd>Delete</kbd> key [#9473](https://github.com/JabRef/jabref/issues/9473)
 
 
 ### Fixed
diff --git a/src/main/java/org/jabref/gui/fieldeditors/LinkedFileViewModel.java b/src/main/java/org/jabref/gui/fieldeditors/LinkedFileViewModel.java
index f18975dad88..1e3daafffe7 100644
--- a/src/main/java/org/jabref/gui/fieldeditors/LinkedFileViewModel.java
+++ b/src/main/java/org/jabref/gui/fieldeditors/LinkedFileViewModel.java
@@ -385,7 +385,7 @@ public boolean delete() {
         Optional<Path> file = linkedFile.findIn(databaseContext, preferences.getFilePreferences());
 
         if (file.isEmpty()) {
-            LOGGER.warn("Could not find file " + linkedFile.getLink());
+            LOGGER.warn("Could not find file {}", linkedFile.getLink());
             return true;
         }
 
@@ -407,7 +407,7 @@ public boolean delete() {
                     return true;
                 } catch (IOException ex) {
                     dialogService.showErrorDialogAndWait(Localization.lang("Cannot delete file"), Localization.lang("File permission error"));
-                    LOGGER.warn("File permission error while deleting: " + linkedFile, ex);
+                    LOGGER.warn("File permission error while deleting: {}", linkedFile, ex);
                 }
             }
         }
diff --git a/src/main/java/org/jabref/gui/fieldeditors/LinkedFilesEditor.java b/src/main/java/org/jabref/gui/fieldeditors/LinkedFilesEditor.java
index e93c3952858..b59d1a3164d 100644
--- a/src/main/java/org/jabref/gui/fieldeditors/LinkedFilesEditor.java
+++ b/src/main/java/org/jabref/gui/fieldeditors/LinkedFilesEditor.java
@@ -1,6 +1,5 @@
 package org.jabref.gui.fieldeditors;
 
-import java.util.List;
 import java.util.Optional;
 
 import javafx.beans.binding.Bindings;
@@ -41,6 +40,7 @@
 import org.jabref.gui.icon.IconTheme;
 import org.jabref.gui.importer.GrobidOptInDialogHelper;
 import org.jabref.gui.keyboard.KeyBinding;
+import org.jabref.gui.linkedfile.DeleteFileAction;
 import org.jabref.gui.util.BindingsHelper;
 import org.jabref.gui.util.TaskExecutor;
 import org.jabref.gui.util.ViewModelListCellFactory;
@@ -218,10 +218,8 @@ private void setUpKeyBindings() {
             if (keyBinding.isPresent()) {
                 switch (keyBinding.get()) {
                     case DELETE_ENTRY:
-                        List<LinkedFileViewModel> toBeDeleted = List.copyOf(listView.getSelectionModel().getSelectedItems());
-                        for (LinkedFileViewModel selectedItem : toBeDeleted) {
-                            viewModel.deleteFile(selectedItem);
-                        }
+                        new DeleteFileAction(dialogService, preferencesService, databaseContext,
+                                viewModel, listView).execute();
                         event.consume();
                         break;
                     default:
diff --git a/src/main/java/org/jabref/gui/linkedfile/DeleteFileAction.java b/src/main/java/org/jabref/gui/linkedfile/DeleteFileAction.java
new file mode 100644
index 00000000000..a1f9ef3bb15
--- /dev/null
+++ b/src/main/java/org/jabref/gui/linkedfile/DeleteFileAction.java
@@ -0,0 +1,138 @@
+package org.jabref.gui.linkedfile;
+
+import java.io.IOException;
+import java.nio.file.Files;
+import java.nio.file.Path;
+import java.util.List;
+import java.util.Optional;
+
+import javafx.scene.control.Alert;
+import javafx.scene.control.ButtonBar;
+import javafx.scene.control.ButtonType;
+import javafx.scene.control.ListView;
+
+import org.jabref.gui.DialogService;
+import org.jabref.gui.actions.SimpleCommand;
+import org.jabref.gui.fieldeditors.LinkedFileViewModel;
+import org.jabref.gui.fieldeditors.LinkedFilesEditorViewModel;
+import org.jabref.logic.l10n.Localization;
+import org.jabref.model.database.BibDatabaseContext;
+import org.jabref.model.entry.LinkedFile;
+import org.jabref.preferences.PreferencesService;
+
+import org.slf4j.Logger;
+import org.slf4j.LoggerFactory;
+
+public class DeleteFileAction extends SimpleCommand {
+
+    private static final Logger LOGGER = LoggerFactory.getLogger(DeleteFileAction.class);
+
+    private final DialogService dialogService;
+    private final PreferencesService preferences;
+    private final BibDatabaseContext databaseContext;
+    private final LinkedFilesEditorViewModel viewModel;
+    private final ListView<LinkedFileViewModel> listView;
+
+    public DeleteFileAction(DialogService dialogService,
+                            PreferencesService preferences,
+                            BibDatabaseContext databaseContext,
+                            LinkedFilesEditorViewModel viewModel,
+                            ListView<LinkedFileViewModel> listView) {
+        this.dialogService = dialogService;
+        this.preferences = preferences;
+        this.databaseContext = databaseContext;
+        this.viewModel = viewModel;
+        this.listView = listView;
+    }
+
+    @Override
+    public void execute() {
+        List<LinkedFileViewModel> toBeDeleted = List.copyOf(listView.getSelectionModel().getSelectedItems());
+
+        if (toBeDeleted.isEmpty()) {
+            dialogService.notify(Localization.lang("This operation requires selected linked files."));
+            return;
+        }
+
+        String dialogTitle;
+        String dialogContent;
+
+        if (toBeDeleted.size() != 1) {
+            dialogTitle = Localization.lang("Delete %0 files", toBeDeleted.size());
+            dialogContent = Localization.lang("Delete %0 files permanently from disk, or just remove the files from the entry? " +
+                    "Pressing Delete will delete the files permanently from disk.", toBeDeleted.size());
+        } else {
+            Optional<Path> file = toBeDeleted.get(0).getFile().findIn(databaseContext, preferences.getFilePreferences());
+
+            if (file.isPresent()) {
+                dialogTitle = Localization.lang("Delete '%0'", file.get().getFileName().toString());
+                dialogContent = Localization.lang("Delete '%0' permanently from disk, or just remove the file from the entry? " +
+                        "Pressing Delete will delete the file permanently from disk.", file.get().toString());
+            } else {
+                dialogService.notify(Localization.lang("Error accessing file '%0'.", toBeDeleted.get(0).getFile().getLink()));
+                return;
+            }
+        }
+
+        ButtonType removeFromEntry = new ButtonType(Localization.lang("Remove from entry"), ButtonBar.ButtonData.YES);
+        ButtonType deleteFromEntry = new ButtonType(Localization.lang("Delete from disk"));
+        Optional<ButtonType> buttonType = dialogService.showCustomButtonDialogAndWait(Alert.AlertType.INFORMATION,
+                dialogTitle, dialogContent, removeFromEntry, deleteFromEntry, ButtonType.CANCEL);
+
+        if (buttonType.isPresent()) {
+            if (buttonType.get().equals(removeFromEntry)) {
+                deleteFiles(toBeDeleted, false);
+            }
+
+            if (buttonType.get().equals(deleteFromEntry)) {
+                deleteFiles(toBeDeleted, true);
+            }
+        }
+    }
+
+    /**
+     * Deletes the files from the entry and optionally from disk.
+     *
+     * @param toBeDeleted the files to be deleted
+     * @param deleteFromDisk if true, the files are deleted from disk, otherwise they are only removed from the entry
+     */
+    private void deleteFiles(List<LinkedFileViewModel> toBeDeleted, boolean deleteFromDisk) {
+        for (LinkedFileViewModel fileViewModel : toBeDeleted) {
+            if (fileViewModel.getFile().isOnlineLink()) {
+                viewModel.removeFileLink(fileViewModel);
+            } else {
+                if (deleteFromDisk) {
+                    deleteFileFromDisk(fileViewModel);
+                }
+                viewModel.getFiles().remove(fileViewModel);
+            }
+        }
+    }
+
+    /**
+     * Deletes the file from disk without asking the user for confirmation.
+     *
+     * @param fileViewModel the file to be deleted
+     */
+    public void deleteFileFromDisk(LinkedFileViewModel fileViewModel) {
+        LinkedFile linkedFile = fileViewModel.getFile();
+
+        Optional<Path> file = linkedFile.findIn(databaseContext, preferences.getFilePreferences());
+
+        if (file.isEmpty()) {
+            LOGGER.warn("Could not find file {}", linkedFile.getLink());
+        }
+
+        if (file.isPresent()) {
+            try {
+                Files.delete(file.get());
+            } catch (
+                    IOException ex) {
+                dialogService.showErrorDialogAndWait(Localization.lang("Cannot delete file"), Localization.lang("File permission error"));
+                LOGGER.warn("File permission error while deleting: {}", linkedFile, ex);
+            }
+        } else {
+            dialogService.notify(Localization.lang("Error accessing file '%0'.", linkedFile.getLink()));
+        }
+    }
+}
diff --git a/src/main/resources/l10n/JabRef_en.properties b/src/main/resources/l10n/JabRef_en.properties
index 035b291a4fd..c772cf06f87 100644
--- a/src/main/resources/l10n/JabRef_en.properties
+++ b/src/main/resources/l10n/JabRef_en.properties
@@ -2539,3 +2539,8 @@ Please\ select\ a\ valid\ main\ directory\ under=Please select a valid main dire
 Search\ from\ history...=Search from history...
 your\ search\ history\ is\ empty=your search history is empty
 Clear\ history =Clear history
+
+Delete\ %0\ files=Delete %0 files
+Delete\ %0\ files\ permanently\ from\ disk,\ or\ just\ remove\ the\ files\ from\ the\ entry?\ Pressing\ Delete\ will\ delete\ the\ files\ permanently\ from\ disk.=Delete %0 files permanently from disk, or just remove the files from the entry? Pressing Delete will delete the files permanently from disk.
+Error\ accessing\ file\ '%0'.=Error accessing file '%0'.
+This\ operation\ requires\ selected\ linked\ files.=This operation requires selected linked files.