diff --git a/tools/environments/daytona.py b/tools/environments/daytona.py
index 89ca041b8a..490e5bed47 100644
--- a/tools/environments/daytona.py
+++ b/tools/environments/daytona.py
@@ -16,7 +16,7 @@ from tools.environments.base import (
     BaseEnvironment,
     _ThreadedProcessHandle,
 )
-from tools.environments.file_sync import FileSyncManager, iter_sync_files, quoted_rm_command
+from tools.environments.file_sync import BulkUploadFn, FileSyncManager, iter_sync_files, quoted_rm_command
 
 logger = logging.getLogger(__name__)
 
@@ -129,6 +129,7 @@ class DaytonaEnvironment(BaseEnvironment):
             get_files_fn=lambda: iter_sync_files(f"{self._remote_home}/.hermes"),
             upload_fn=self._daytona_upload,
             delete_fn=self._daytona_delete,
+            bulk_upload_fn=self._daytona_bulk_upload,
         )
         self._sync_manager.sync(force=True)
         self.init_session()
@@ -139,6 +140,30 @@ class DaytonaEnvironment(BaseEnvironment):
         self._sandbox.process.exec(f"mkdir -p {parent}")
         self._sandbox.fs.upload_file(host_path, remote_path)
 
+    def _daytona_bulk_upload(self, files: list[tuple[str, str]]) -> None:
+        """Upload many files in a single HTTP call via Daytona SDK.
+
+        Uses ``sandbox.fs.upload_files()`` which batches all files into one
+        multipart POST, avoiding per-file TLS/HTTP overhead (~580 files
+        goes from ~5 min to <2 s).
+        """
+        from daytona.common.filesystem import FileUpload
+
+        if not files:
+            return
+
+        # Pre-create all unique parent directories in one shell call
+        parents = sorted({str(Path(remote).parent) for _, remote in files})
+        if parents:
+            mkdir_cmd = "mkdir -p " + " ".join(shlex.quote(p) for p in parents)
+            self._sandbox.process.exec(mkdir_cmd)
+
+        uploads = [
+            FileUpload(source=host_path, destination=remote_path)
+            for host_path, remote_path in files
+        ]
+        self._sandbox.fs.upload_files(uploads)
+
     def _daytona_delete(self, remote_paths: list[str]) -> None:
         """Batch-delete remote files via SDK exec."""
         self._sandbox.process.exec(quoted_rm_command(remote_paths))
diff --git a/tools/environments/file_sync.py b/tools/environments/file_sync.py
index fb5559a93a..29b45f858f 100644
--- a/tools/environments/file_sync.py
+++ b/tools/environments/file_sync.py
@@ -21,6 +21,7 @@ _FORCE_SYNC_ENV = "HERMES_FORCE_FILE_SYNC"
 
 # Transport callbacks provided by each backend
 UploadFn = Callable[[str, str], None]  # (host_path, remote_path) -> raises on failure
+BulkUploadFn = Callable[[list[tuple[str, str]]], None]  # [(host_path, remote_path), ...] -> raises on failure
 DeleteFn = Callable[[list[str]], None]  # (remote_paths) -> raises on failure
 GetFilesFn = Callable[[], list[tuple[str, str]]]  # () -> [(host_path, remote_path), ...]
 
@@ -76,9 +77,11 @@ class FileSyncManager:
         upload_fn: UploadFn,
         delete_fn: DeleteFn,
         sync_interval: float = _SYNC_INTERVAL_SECONDS,
+        bulk_upload_fn: BulkUploadFn | None = None,
     ):
         self._get_files_fn = get_files_fn
         self._upload_fn = upload_fn
+        self._bulk_upload_fn = bulk_upload_fn
         self._delete_fn = delete_fn
         self._synced_files: dict[str, tuple[float, int]] = {}  # remote_path -> (mtime, size)
         self._last_sync_time: float = 0.0  # monotonic; 0 ensures first sync runs
@@ -129,9 +132,13 @@ class FileSyncManager:
             logger.debug("file_sync: deleting %d stale remote file(s)", len(to_delete))
 
         try:
-            for host_path, remote_path in to_upload:
-                self._upload_fn(host_path, remote_path)
-                logger.debug("file_sync: uploaded %s -> %s", host_path, remote_path)
+            if to_upload and self._bulk_upload_fn is not None:
+                self._bulk_upload_fn(to_upload)
+                logger.debug("file_sync: bulk-uploaded %d file(s)", len(to_upload))
+            else:
+                for host_path, remote_path in to_upload:
+                    self._upload_fn(host_path, remote_path)
+                    logger.debug("file_sync: uploaded %s -> %s", host_path, remote_path)
 
             if to_delete:
                 self._delete_fn(to_delete)