diff --git a/backend/api/cloud/operations.py b/backend/api/cloud/operations.py
index f4680ef..74a2eef 100644
--- a/backend/api/cloud/operations.py
+++ b/backend/api/cloud/operations.py
@@ -892,6 +892,24 @@ async def delete_cloud_item(
     if kind == MUT_KIND_DELETED:
         # Success: reconcile before returning (T-13-29)
 
+        # CR-04: Soft-delete the CloudItem row so that queries filtering on
+        # deleted_at.is_(None) (upload conflict check, preview, download) no longer
+        # "see" the deleted file. Without this, the row persists until the next full
+        # provider re-list, causing false conflict hits on immediate re-upload.
+        from datetime import datetime, timezone
+        from sqlalchemy import update as sa_update
+
+        await session.execute(
+            sa_update(CloudItem)
+            .where(
+                CloudItem.connection_id == connection_id,
+                CloudItem.provider_item_id == item_id,
+                CloudItem.user_id == current_user.id,
+                CloudItem.deleted_at.is_(None),
+            )
+            .values(deleted_at=datetime.now(timezone.utc))
+        )
+
         # Invalidate parent folder so next browse reflects the deletion
         invalidate_parent = item_parent_ref if item_parent_ref is not None else ""
         await update_folder_state(