diff --git a/clients/desktop/src-tauri/src/cloud_files/windows.rs b/clients/desktop/src-tauri/src/cloud_files/windows.rs
index 4e16c44..d397a61 100644
--- a/clients/desktop/src-tauri/src/cloud_files/windows.rs
+++ b/clients/desktop/src-tauri/src/cloud_files/windows.rs
@@ -432,18 +432,37 @@ pub fn populate_placeholders(
         std::fs::create_dir_all(&p).ok();
     }
 
-    // Dann Dateien als Platzhalter
+    // Dann Dateien als Platzhalter. Existierende "normale" Dateien
+    // (z.B. nach vorherigem CfUnregisterSyncRoot) vorher loeschen,
+    // weil CfCreatePlaceholders sonst mit ERROR_FILE_EXISTS scheitert
+    // und die Datei nie zum Platzhalter wird -> spaeter koennte man
+    // sie nicht mehr dehydrieren (0x80070178 "keine Clouddatei").
     for e in entries.iter().filter(|e| !e.is_folder) {
         let rel = rel_path(e, &by_id);
+        let full = mount_point.join(&rel);
         let parent = rel
             .parent()
             .map(|p| mount_point.join(p))
             .unwrap_or_else(|| mount_point.clone());
         let identity = e.id.to_string();
-        if let Err(err) =
-            create_placeholder(&parent, &e.name, e.size, &e.modified_at, identity.as_bytes())
-        {
-            eprintln!("placeholder {}: {}", e.name, err);
+
+        if full.exists() && !is_cfapi_placeholder(&full) {
+            log_msg(mount_point, &format!(
+                "deleting non-placeholder {} to recreate",
+                full.display()
+            ));
+            if let Err(err) = std::fs::remove_file(&full) {
+                log_err(mount_point, &format!(
+                    "remove {} failed: {err}", full.display()
+                ));
+            }
+        }
+
+        match create_placeholder(&parent, &e.name, e.size, &e.modified_at, identity.as_bytes()) {
+            Ok(()) => log_msg(mount_point, &format!("placeholder created: {}", full.display())),
+            Err(err) => log_err(mount_point, &format!(
+                "placeholder {} FAILED: {err}", full.display()
+            )),
         }
     }
     Ok(())