diff --git a/cli/onionshare_cli/__init__.py b/cli/onionshare_cli/__init__.py
index d84a1eec..0dffb493 100644
--- a/cli/onionshare_cli/__init__.py
+++ b/cli/onionshare_cli/__init__.py
@@ -119,6 +119,13 @@ def main(cwd=None):
         default=False,
         help="Share files: Continue sharing after files have been sent (default is to stop sharing)",
     )
+    parser.add_argument(
+        "--log-filenames",
+        action="store_true",
+        dest="log_filenames",
+        default=False,
+        help="Log file download activity to stdout"
+    )
     parser.add_argument(
         "--qr",
         action="store_true",
@@ -204,6 +211,7 @@ def main(cwd=None):
     disable_files = args.disable_files
     disable_csp = bool(args.disable_csp)
     custom_csp = args.custom_csp
+    log_filenames = bool(args.log_filenames)
     verbose = bool(args.verbose)
 
     # Verbose mode?
@@ -242,6 +250,7 @@ def main(cwd=None):
             mode_settings.set("persistent", "mode", mode)
         if mode == "share":
             mode_settings.set("share", "autostop_sharing", autostop_sharing)
+            mode_settings.set("share", "log_filenames", log_filenames)
         if mode == "receive":
             if data_dir:
                 mode_settings.set("receive", "data_dir", data_dir)
@@ -259,6 +268,7 @@ def main(cwd=None):
             if custom_csp:
                 mode_settings.set("website", "custom_csp", custom_csp)
                 mode_settings.set("website", "disable_csp", False)
+            mode_settings.set("website", "log_filenames", log_filenames)
     else:
         # See what the persistent mode was
         mode = mode_settings.get("persistent", "mode")
diff --git a/cli/onionshare_cli/mode_settings.py b/cli/onionshare_cli/mode_settings.py
index 90bcaf07..c920ab66 100644
--- a/cli/onionshare_cli/mode_settings.py
+++ b/cli/onionshare_cli/mode_settings.py
@@ -48,14 +48,23 @@ class ModeSettings:
                 "autostop_timer": False,
                 "service_id": None,
             },
-            "share": {"autostop_sharing": True, "filenames": []},
+            "share": {
+                "autostop_sharing": True,
+                "filenames": [],
+                "log_filenames": False,
+            },
             "receive": {
                 "data_dir": self.build_default_receive_data_dir(),
                 "webhook_url": None,
                 "disable_text": False,
                 "disable_files": False,
             },
-            "website": {"disable_csp": False, "custom_csp": None, "filenames": []},
+            "website": {
+                "disable_csp": False,
+                "custom_csp": None,
+                "log_filenames": False,
+                "filenames": []
+            },
             "chat": {},
         }
         self._settings = {}
diff --git a/cli/onionshare_cli/web/send_base_mode.py b/cli/onionshare_cli/web/send_base_mode.py
index ca79b99f..5d6af460 100644
--- a/cli/onionshare_cli/web/send_base_mode.py
+++ b/cli/onionshare_cli/web/send_base_mode.py
@@ -245,8 +245,14 @@ class SendBaseModeWeb:
                             or self.common.platform == "Linux"
                             or self.common.platform == "BSD"
                         ):
+                            if self.web.settings.get(self.web.mode, "log_filenames"):
+                                filename_str = f"{path} - "
+                            else:
+                                filename_str = ""
+                            
                             sys.stdout.write(
-                                "\r{0:s}, {1:.2f}%          ".format(
+                                "\r{0}{1:s}, {2:.2f}%          ".format(
+                                    filename_str,
                                     self.common.human_readable_filesize(
                                         downloaded_bytes
                                     ),
@@ -278,8 +284,7 @@ class SendBaseModeWeb:
 
             fp.close()
 
-            if self.common.platform != "Darwin":
-                sys.stdout.write("\n")
+            sys.stdout.write("\n")
 
         basename = os.path.basename(filesystem_path)
 
diff --git a/cli/onionshare_cli/web/share_mode.py b/cli/onionshare_cli/web/share_mode.py
index 6af4ae0b..276a7be8 100644
--- a/cli/onionshare_cli/web/share_mode.py
+++ b/cli/onionshare_cli/web/share_mode.py
@@ -346,8 +346,14 @@ class ShareModeWeb(SendBaseModeWeb):
                         or self.common.platform == "Linux"
                         or self.common.platform == "BSD"
                     ):
+                        if self.web.settings.get("share", "log_filenames"):
+                            filename_str = f"{path} - "
+                        else:
+                            filename_str = ""
+
                         sys.stdout.write(
-                            "\r{0:s}, {1:.2f}%          ".format(
+                            "\r{0}{1:s}, {2:.2f}%          ".format(
+                                filename_str,
                                 self.common.human_readable_filesize(downloaded_bytes),
                                 percent,
                             )
@@ -376,8 +382,7 @@ class ShareModeWeb(SendBaseModeWeb):
 
         fp.close()
 
-        if self.common.platform != "Darwin":
-            sys.stdout.write("\n")
+        sys.stdout.write("\n")
 
         # Download is finished
         if self.web.settings.get("share", "autostop_sharing"):