diff --git a/cli/onionshare_cli/__init__.py b/cli/onionshare_cli/__init__.py
index c40bf6a0..1bd0582c 100644
--- a/cli/onionshare_cli/__init__.py
+++ b/cli/onionshare_cli/__init__.py
@@ -193,6 +193,12 @@ def main(cwd=None):
         default=None,
         help="Receive files: Save files received to this directory",
     )
+    parser.add_argument(
+        "--webhook-url",
+        metavar="webhook_url",
+        default=None,
+        help="Receive files: URL to receive webhook notifications",
+    )
     # Website args
     parser.add_argument(
         "--disable_csp",
@@ -235,6 +241,7 @@ def main(cwd=None):
     client_auth = bool(args.client_auth)
     autostop_sharing = not bool(args.no_autostop_sharing)
     data_dir = args.data_dir
+    webhook_url = args.webhook_url
     disable_csp = bool(args.disable_csp)
     verbose = bool(args.verbose)
 
@@ -283,6 +290,8 @@ def main(cwd=None):
         if mode == "receive":
             if data_dir:
                 mode_settings.set("receive", "data_dir", data_dir)
+            if webhook_url:
+                mode_settings.set("receive", "webhook_url", webhook_url)
         if mode == "website":
             mode_settings.set("website", "disable_csp", disable_csp)
     else:
@@ -354,10 +363,23 @@ def main(cwd=None):
     # Start the onionshare app
     try:
         common.settings.load()
-        if not mode_settings.get("general", "public"):
-            web.generate_password(mode_settings.get("onion", "password"))
-        else:
+
+        if mode_settings.get("general", "public"):
             web.password = None
+        else:
+            web.generate_password(mode_settings.get("onion", "password"))
+
+        # Receive mode needs to know the tor proxy details for webhooks
+        if mode == "receive":
+            if local_only:
+                web.proxies = None
+            else:
+                (socks_address, socks_port) = onion.get_tor_socks_port()
+                web.proxies = {
+                    "http": f"socks5://{socks_address}:{socks_port}",
+                    "https": f"socks5://{socks_address}:{socks_port}",
+                }
+
         app = OnionShare(common, onion, local_only, autostop_timer)
         app.choose_port()
 
diff --git a/cli/onionshare_cli/mode_settings.py b/cli/onionshare_cli/mode_settings.py
index 4f105653..c2e5e6cd 100644
--- a/cli/onionshare_cli/mode_settings.py
+++ b/cli/onionshare_cli/mode_settings.py
@@ -50,7 +50,10 @@ class ModeSettings:
                 "service_id": None,
             },
             "share": {"autostop_sharing": True, "filenames": []},
-            "receive": {"data_dir": self.build_default_receive_data_dir()},
+            "receive": {
+                "data_dir": self.build_default_receive_data_dir(),
+                "webhook_url": None,
+            },
             "website": {"disable_csp": False, "filenames": []},
             "chat": {"room": "default"},
         }
diff --git a/cli/onionshare_cli/web/receive_mode.py b/cli/onionshare_cli/web/receive_mode.py
index 62415578..d3bd3c2b 100644
--- a/cli/onionshare_cli/web/receive_mode.py
+++ b/cli/onionshare_cli/web/receive_mode.py
@@ -21,6 +21,7 @@ along with this program.  If not, see <http://www.gnu.org/licenses/>.
 import os
 import tempfile
 import json
+import requests
 from datetime import datetime
 from flask import Request, request, render_template, make_response, flash, redirect
 from werkzeug.utils import secure_filename
@@ -101,6 +102,14 @@ class ReceiveModeWeb:
                     )
                     print(f"\nReceived: {local_path}")
 
+            # Send webhook if configured
+            if (
+                self.web.settings.get("receive", "webhook_url")
+                and not request.upload_error
+                and len(files) > 0
+            ):
+                self.send_websocket_notification(f"{len(files)} files uploaded")
+
             if request.upload_error:
                 self.common.log(
                     "ReceiveModeWeb",
@@ -172,6 +181,22 @@ class ReceiveModeWeb:
                 return self.web.error403()
             return upload(ajax=True)
 
+    def send_websocket_notification(self, data):
+        self.common.log("ReceiveModeWeb", "send_websocket_notification", data)
+        try:
+            requests.post(
+                self.web.settings.get("receive", "webhook_url"),
+                data=data,
+                timeout=5,
+                proxies=self.web.proxies,
+            )
+        except Exception as e:
+            self.common.log(
+                "ReceiveModeWeb",
+                "send_websocket_notification",
+                f"sending failed: {e}",
+            )
+
 
 class ReceiveModeWSGIMiddleware(object):
     """