diff --git a/src/main/java/org/jabref/preferences/JabRefPreferences.java b/src/main/java/org/jabref/preferences/JabRefPreferences.java
index fe106584d86..160dc1798d0 100644
--- a/src/main/java/org/jabref/preferences/JabRefPreferences.java
+++ b/src/main/java/org/jabref/preferences/JabRefPreferences.java
@@ -40,7 +40,6 @@
 import org.jabref.gui.Globals;
 import org.jabref.gui.autocompleter.AutoCompleteFirstNameMode;
 import org.jabref.gui.autocompleter.AutoCompletePreferences;
-import org.jabref.gui.desktop.JabRefDesktop;
 import org.jabref.gui.duplicationFinder.DuplicateResolverDialog;
 import org.jabref.gui.entryeditor.EntryEditorPreferences;
 import org.jabref.gui.externalfiletype.ExternalFileType;
@@ -710,7 +709,6 @@ private JabRefPreferences() {
         defaults.put(WARN_BEFORE_OVERWRITING_KEY, Boolean.TRUE);
         defaults.put(CONFIRM_DELETE, Boolean.TRUE);
         defaults.put(CONFIRM_LINKED_FILE_DELETE, Boolean.TRUE);
-        defaults.put(TRASH_INSTEAD_OF_DELETE, JabRefDesktop.moveToTrashSupported());
         defaults.put(DEFAULT_CITATION_KEY_PATTERN, "[auth][year]");
         defaults.put(UNWANTED_CITATION_KEY_CHARACTERS, "-`ʹ:!;?^+");
         defaults.put(RESOLVE_STRINGS_FOR_FIELDS, "author;booktitle;editor;editora;editorb;editorc;institution;issuetitle;journal;journalsubtitle;journaltitle;mainsubtitle;month;publisher;shortauthor;shorteditor;subtitle;titleaddon");
@@ -2204,7 +2202,8 @@ public FilePreferences getFilePreferences() {
                 // We choose the data directory, because a ".bak" file should survive cache cleanups
                 getPath(BACKUP_DIRECTORY, OS.getNativeDesktop().getBackupDirectory()),
                 getBoolean(CONFIRM_LINKED_FILE_DELETE),
-                getBoolean(TRASH_INSTEAD_OF_DELETE));
+                // We make use of the fallback, because we need AWT being initialized, which is not the case at the constructor JabRefPreferences()
+                getBoolean(TRASH_INSTEAD_OF_DELETE, OS.getNativeDesktop().moveToTrashSupported()));
 
         EasyBind.listen(getInternalPreferences().getUserAndHostProperty(), (obs, oldValue, newValue) -> filePreferences.getUserAndHostProperty().setValue(newValue));
         EasyBind.listen(filePreferences.mainFileDirectoryProperty(), (obs, oldValue, newValue) -> put(MAIN_FILE_DIRECTORY, newValue));