diff --git a/.github/workflows/tests.yml b/.github/workflows/tests.yml
index 911e0af5..1b5b969e 100644
--- a/.github/workflows/tests.yml
+++ b/.github/workflows/tests.yml
@@ -34,6 +34,7 @@ jobs:
           poetry run onionshare-cli --local-only --receive --auto-stop-timer 2 --qr --verbose
           poetry run onionshare-cli --local-only --website ../docs --auto-stop-timer 2 --qr --verbose
           poetry run onionshare-cli --local-only --chat --auto-stop-timer 5 --qr --verbose
+          touch /tmp/foo{1,2} && poetry run onionshare-cli --local-only --persistent tests/persistent.json --auto-stop-timer 5 --verbose
 
   test-desktop:
     runs-on: ubuntu-latest
diff --git a/cli/onionshare_cli/__init__.py b/cli/onionshare_cli/__init__.py
index 3ea0d76d..e15ecda1 100644
--- a/cli/onionshare_cli/__init__.py
+++ b/cli/onionshare_cli/__init__.py
@@ -33,6 +33,7 @@ from .onionshare import OnionShare
 from .mode_settings import ModeSettings
 from qrcode import QRCode
 
+
 def main(cwd=None):
     """
     The main() function implements all of the logic that the command-line version of
@@ -124,7 +125,7 @@ def main(cwd=None):
         action="store_true",
         dest="log_filenames",
         default=False,
-        help="Log file download activity to stdout"
+        help="Log file download activity to stdout",
     )
     parser.add_argument(
         "--qr",
@@ -260,7 +261,9 @@ def main(cwd=None):
             mode_settings.set("receive", "disable_files", disable_files)
         if mode == "website":
             if disable_csp and custom_csp:
-                print("You cannot disable the CSP and set a custom one. Either set --disable-csp or --custom-csp but not both.")
+                print(
+                    "You cannot disable the CSP and set a custom one. Either set --disable-csp or --custom-csp but not both."
+                )
                 sys.exit()
             if disable_csp:
                 mode_settings.set("website", "disable_csp", True)
@@ -277,19 +280,18 @@ def main(cwd=None):
     if mode == "share" or mode == "website":
         # Unless you passed in a persistent filename, in which case get the filenames from
         # the mode settings
-        if (
-            persistent_filename
-            and not mode_settings.just_created
-            and len(filenames) != 0
-        ):
+        if persistent_filename and not mode_settings.just_created:
+            # The assumption is that if we didn't just create the mode settings,
+            # this persistent json file already has validated the filenames
+            # defined therein.
             filenames = mode_settings.get(mode, "filenames")
-
         else:
-            # Make sure filenames given if not using receiver mode
+            # Make sure filenames given. If it is somehow empty yet we had a persistent
+            # json file, something has gone wrong with that file, just remove it.
             if len(filenames) == 0:
                 if persistent_filename:
                     mode_settings.delete()
-
+                print("No file(s) were provided")
                 parser.print_help()
                 sys.exit()
 
@@ -515,7 +517,11 @@ def main(cwd=None):
                 if not app.autostop_timer_thread.is_alive():
                     if mode == "share":
                         # If there were no attempts to download the share, or all downloads are done, we can stop
-                        if not web.share_mode.download_in_progress or web.share_mode.cur_history_id == 0 or web.done:
+                        if (
+                            not web.share_mode.download_in_progress
+                            or web.share_mode.cur_history_id == 0
+                            or web.done
+                        ):
                             print("Stopped because auto-stop timer ran out")
                             web.stop(app.port)
                             break
diff --git a/cli/onionshare_cli/mode_settings.py b/cli/onionshare_cli/mode_settings.py
index cfd9971c..a534a181 100644
--- a/cli/onionshare_cli/mode_settings.py
+++ b/cli/onionshare_cli/mode_settings.py
@@ -51,6 +51,7 @@ class ModeSettings:
                 "autostart_timer": False,
                 "autostop_timer": False,
                 "service_id": None,
+                "qr": False
             },
             "share": {
                 "autostop_sharing": True,
diff --git a/cli/tests/persistent.json b/cli/tests/persistent.json
new file mode 100644
index 00000000..ab2f31d2
--- /dev/null
+++ b/cli/tests/persistent.json
@@ -0,0 +1,41 @@
+{
+  "onion": {
+    "private_key": "cDGn/lagkwEa62rj+SxSXqFjfSG08fVLVDyZ8HgOS32J9JorEPPWVjDF3GRFolqDTNeUpqNDy39j0E86tqbJag==",
+    "client_auth_priv_key": "TYIU3TRRXWCQBSJYYRKOTR35M32YWNKQ3VBDGFDR74ASOW243OTA",
+    "client_auth_pub_key": "62VXAPXH5HTODLCGL7CNZHA3Q3OKJEPVLV2UGUKQUCZ5GW3YTAAQ"
+  },
+  "persistent": {
+    "mode": "share",
+    "enabled": true,
+    "autostart_on_launch": false
+  },
+  "general": {
+    "title": null,
+    "public": false,
+    "autostart_timer": false,
+    "autostop_timer": true,
+    "service_id": "frlqrdrt4arsgnp4xenzoug5osmfqaqdbniuf4ziejoiwnhju3jlazid",
+    "qr": false
+  },
+  "share": {
+    "autostop_sharing": false,
+    "filenames": [
+      "/tmp/foo1",
+      "/tmp/foo2"
+    ],
+    "log_filenames": false
+  },
+  "receive": {
+    "data_dir": "/tmp",
+    "webhook_url": null,
+    "disable_text": false,
+    "disable_files": false
+  },
+  "website": {
+    "disable_csp": false,
+    "custom_csp": null,
+    "log_filenames": false,
+    "filenames": []
+  },
+  "chat": {}
+}
\ No newline at end of file