diff --git a/test-infra/s3_cache.py b/test-infra/s3_cache.py
index 8f8ffd11df..eaa37992db 100755
--- a/test-infra/s3_cache.py
+++ b/test-infra/s3_cache.py
@@ -1,12 +1,13 @@
 #!/usr/bin/env python2.7
+# pylint: disable=C0301
 from __future__ import absolute_import, unicode_literals, print_function, division
 
 from sys import argv
 from os import environ, stat, chdir, remove as _delete_file
-from os.path import isfile, dirname, basename, abspath, realpath, expandvars
+from os.path import dirname, basename, abspath, realpath, expandvars
 from hashlib import sha256
 from subprocess import check_call as run
-from json import load
+from json import load, dump as save
 from contextlib import contextmanager
 from datetime import datetime
 
@@ -16,7 +17,7 @@ from boto.exception import S3ResponseError
 
 
 CONFIG_FILE = './S3Cachefile.json'
-NEED_TO_UPLOAD_MARKER = '.need-to-upload'
+UPLOAD_TODO_FILE = './S3CacheTodo.json'
 BYTES_PER_MB = 1024 * 1024
 
 
@@ -29,6 +30,24 @@ def timer():
     print("\tDone. Took", int(elapsed.total_seconds()), "second(s).")
 
 
+@contextmanager
+def todo_file(writeback=True):
+    try:
+        with open(UPLOAD_TODO_FILE, 'rt') as json_file:
+            todo = load(json_file)
+    except (IOError, OSError, ValueError):
+        todo = {}
+
+    yield todo
+
+    if writeback:
+        try:
+            with open(UPLOAD_TODO_FILE, 'wt') as json_file:
+                save(todo, json_file)
+        except (OSError, IOError) as save_err:
+            print("Error saving {}:".format(UPLOAD_TODO_FILE), save_err)
+
+
 def _sha256_of_file(filename):
     hasher = sha256()
     with open(filename, 'rb') as input_file:
@@ -45,6 +64,21 @@ def _delete_file_quietly(filename):
         pass
 
 
+def mark_needs_uploading(cache_name):
+    with todo_file() as todo:
+        todo[cache_name] = True
+
+
+def mark_uploaded(cache_name):
+    with todo_file() as todo:
+        todo.pop(cache_name, None)
+
+
+def need_to_upload(cache_name):
+    with todo_file(writeback=False) as todo:
+        return todo.get(cache_name, False)
+
+
 def _tarball_size(directory):
     kib = stat(_tarball_filename_for(directory)).st_size // BYTES_PER_MB
     return "{} MiB".format(kib)
@@ -67,14 +101,13 @@ def _extract_tarball(directory):
 
 
 def download(directory):
-    _delete_file_quietly(NEED_TO_UPLOAD_MARKER)
+    mark_uploaded(cache_name)  # reset
     try:
         print("Downloading {} tarball from S3...".format(cache_name))
         with timer():
             key.get_contents_to_filename(_tarball_filename_for(directory))
     except S3ResponseError as err:
-        open(NEED_TO_UPLOAD_MARKER, 'a').close()
-        print(err)
+        mark_needs_uploading(cache_name)
         raise SystemExit("Cached {} download failed!".format(cache_name))
     print("Downloaded {}.".format(_tarball_size(directory)))
     _extract_tarball(directory)
@@ -87,7 +120,7 @@ def upload(directory):
     with timer():
         key.set_contents_from_filename(_tarball_filename_for(directory))
     print("{} cache successfully updated.".format(cache_name))
-    _delete_file_quietly(NEED_TO_UPLOAD_MARKER)
+    mark_uploaded(cache_name)
 
 
 if __name__ == '__main__':
@@ -135,7 +168,7 @@ if __name__ == '__main__':
         if mode == 'download':
             download(directory)
         elif mode == 'upload':
-            if isfile(NEED_TO_UPLOAD_MARKER):  # FIXME
+            if need_to_upload(cache_name):
                 upload(directory)
             else:
                 print("No need to upload anything.")