Merge pull request #1677 from onionshare/update-deps

Update deps & switch to waitress for running flask servers

18 files changed, 963 insertions, 536 deletions

diff --git a/.github/dependabot.yml b/.github/dependabot.yml
index bc96ed26..f58644be 100644
--- a/.github/dependabot.yml
+++ b/.github/dependabot.yml
@@ -10,3 +10,8 @@ updates:
     directory: "/desktop"
     schedule:
       interval: "weekly"
+
+  - package-ecosystem: "poetry"
+    directory: "/docs"
+    schedule:
+      interval: "weekly"
\ No newline at end of file
diff --git a/.github/workflows/tests.yml b/.github/workflows/tests.yml
index aebfe8eb..f124a4bd 100644
--- a/.github/workflows/tests.yml
+++ b/.github/workflows/tests.yml
@@ -29,10 +29,10 @@ jobs:
       - run: |
           cd cli
           poetry run pytest -v ./tests
-          poetry run onionshare-cli --local-only ./tests --auto-stop-timer 2
-          poetry run onionshare-cli --local-only --receive --auto-stop-timer 2
-          poetry run onionshare-cli --local-only --website ../docs --auto-stop-timer 2
-          poetry run onionshare-cli --local-only --chat --auto-stop-timer 2
+          poetry run onionshare-cli --local-only ./tests --auto-stop-timer 2 --verbose
+          poetry run onionshare-cli --local-only --receive --auto-stop-timer 2 --verbose
+          poetry run onionshare-cli --local-only --website ../docs --auto-stop-timer 2 --verbose
+          poetry run onionshare-cli --local-only --chat --auto-stop-timer 5 --verbose
 
   test-desktop:
     runs-on: ubuntu-latest
diff --git a/cli/onionshare_cli/web/send_base_mode.py b/cli/onionshare_cli/web/send_base_mode.py
index d690c98d..d8cef496 100644
--- a/cli/onionshare_cli/web/send_base_mode.py
+++ b/cli/onionshare_cli/web/send_base_mode.py
@@ -25,7 +25,7 @@ import mimetypes
 import gzip
 from flask import Response, request
 from unidecode import unidecode
-from werkzeug.urls import url_quote
+from urllib.parse import quote
 
 
 class SendBaseModeWeb:
@@ -284,7 +284,7 @@ class SendBaseModeWeb:
         r.headers.set("Content-Length", filesize)
         filename_dict = {
             "filename": unidecode(basename),
-            "filename*": "UTF-8''%s" % url_quote(basename),
+            "filename*": "UTF-8''%s" % quote(basename),
         }
         r.headers.set("Content-Disposition", "inline", **filename_dict)
         (content_type, _) = mimetypes.guess_type(basename, strict=False)
diff --git a/cli/onionshare_cli/web/share_mode.py b/cli/onionshare_cli/web/share_mode.py
index f714081d..6af4ae0b 100644
--- a/cli/onionshare_cli/web/share_mode.py
+++ b/cli/onionshare_cli/web/share_mode.py
@@ -29,7 +29,7 @@ from datetime import datetime, timezone
 from flask import Response, request, render_template, make_response, abort
 from unidecode import unidecode
 from werkzeug.http import parse_date, http_date
-from werkzeug.urls import url_quote
+from urllib.parse import quote
 
 from .send_base_mode import SendBaseModeWeb
 
@@ -181,7 +181,6 @@ class ShareModeWeb(SendBaseModeWeb):
 
             # Prepare some variables to use inside generate() function below
             # which is outside of the request context
-            shutdown_func = request.environ.get("werkzeug.server.shutdown")
             request_path = request.path
 
             # If this is a zipped file, then serve as-is. If it's not zipped, then,
@@ -218,7 +217,6 @@ class ShareModeWeb(SendBaseModeWeb):
             else:
                 r = Response(
                     self.generate(
-                        shutdown_func,
                         range_,
                         file_to_download,
                         request_path,
@@ -233,7 +231,7 @@ class ShareModeWeb(SendBaseModeWeb):
             r.headers.set("Content-Length", range_[1] - range_[0] + 1)
             filename_dict = {
                 "filename": unidecode(basename),
-                "filename*": "UTF-8''%s" % url_quote(basename),
+                "filename*": "UTF-8''%s" % quote(basename),
             }
             r.headers.set("Content-Disposition", "attachment", **filename_dict)
             # guess content type
@@ -303,7 +301,7 @@ class ShareModeWeb(SendBaseModeWeb):
         return range_, status_code
 
     def generate(
-        self, shutdown_func, range_, file_to_download, path, history_id, filesize
+        self, range_, file_to_download, path, history_id, filesize
     ):
         # The user hasn't canceled the download
         self.client_cancel = False
@@ -390,9 +388,7 @@ class ShareModeWeb(SendBaseModeWeb):
             print("Stopped because transfer is complete")
             self.web.running = False
             try:
-                if shutdown_func is None:
-                    raise RuntimeError("Not running with the Werkzeug Server")
-                shutdown_func()
+                self.web.stop()
             except Exception:
                 pass
 
diff --git a/cli/onionshare_cli/web/web.py b/cli/onionshare_cli/web/web.py
index 0e7ba6d5..a6ccbeb0 100644
--- a/cli/onionshare_cli/web/web.py
+++ b/cli/onionshare_cli/web/web.py
@@ -23,7 +23,8 @@ import os
 import queue
 import requests
 import shutil
-from distutils.version import LooseVersion as Version
+from packaging.version import Version
+from waitress.server import create_server
 
 import flask
 from flask import (
@@ -35,6 +36,7 @@ from flask import (
     send_file,
     __version__ as flask_version,
 )
+from flask_compress import Compress
 from flask_socketio import SocketIO
 
 from .share_mode import ShareModeWeb
@@ -55,6 +57,12 @@ except Exception:
     pass
 
 
+class WaitressException(Exception):
+    """
+    There was a problem starting the waitress web server.
+    """
+
+
 class Web:
     """
     The Web object is the OnionShare web server, powered by flask
@@ -91,6 +99,8 @@ class Web:
         # https://github.com/onionshare/onionshare/issues/1443
         mimetypes.add_type("text/javascript", ".js")
 
+        self.waitress = None
+
         # The flask app
         self.app = Flask(
             __name__,
@@ -98,6 +108,9 @@ class Web:
             static_url_path=f"/static_{self.common.random_string(16)}",  # randomize static_url_path to avoid making /static unusable
             template_folder=self.common.get_resource_path("templates"),
         )
+        self.compress = Compress()
+        self.compress.init_app(self.app)
+
         self.app.secret_key = self.common.random_string(8)
         self.generate_static_url_path()
 
@@ -251,16 +264,6 @@ class Web:
             mode.cur_history_id += 1
             return self.error500(history_id)
 
-        @self.app.route("/<password_candidate>/shutdown")
-        def shutdown(password_candidate):
-            """
-            Stop the flask web server, from the context of an http request.
-            """
-            if password_candidate == self.shutdown_password:
-                self.force_shutdown()
-                return ""
-            abort(404)
-
         if self.mode != "website":
 
             @self.app.route("/favicon.ico")
@@ -329,25 +332,6 @@ class Web:
         log_handler.setLevel(logging.WARNING)
         self.app.logger.addHandler(log_handler)
 
-    def force_shutdown(self):
-        """
-        Stop the flask web server, from the context of the flask app.
-        """
-        # Shutdown the flask service
-        try:
-            func = request.environ.get("werkzeug.server.shutdown")
-            if func is None and self.mode != "chat":
-                raise RuntimeError("Not running with the Werkzeug Server")
-            func()
-        except Exception:
-            pass
-
-        self.running = False
-
-        # If chat, shutdown the socket server
-        if self.mode == "chat":
-            self.socketio.stop()
-
     def start(self, port):
         """
         Start the flask web server.
@@ -371,7 +355,17 @@ class Web:
         if self.mode == "chat":
             self.socketio.run(self.app, host=host, port=port)
         else:
-            self.app.run(host=host, port=port, threaded=True)
+            try:
+                self.waitress = create_server(
+                    self.app,
+                    host=host,
+                    port=port,
+                    clear_untrusted_proxy_headers=True,
+                    ident="OnionShare",
+                )
+                self.waitress.run()
+            except Exception as e:
+                raise WaitressException(f"Error starting Waitress: {e}")
 
     def stop(self, port):
         """
@@ -382,21 +376,12 @@ class Web:
         # Let the mode know that the user stopped the server
         self.stop_q.put(True)
 
-        # To stop flask, load http://shutdown:[shutdown_password]@127.0.0.1/[shutdown_password]/shutdown
-        # (We're putting the shutdown_password in the path as well to make routing simpler)
-        if self.running:
-            try:
-                requests.get(
-                    f"http://127.0.0.1:{port}/{self.shutdown_password}/shutdown"
-                )
-            except requests.exceptions.ConnectionError as e:
-                # The way flask-socketio stops a connection when running using
-                # eventlet is by raising SystemExit to abort all the processes.
-                # Hence the connections are closed and no response is returned
-                # to the above request. So I am just catching the ConnectionError
-                # to check if it was chat mode, in which case it's okay
-                if self.mode != "chat":
-                    raise e
+        # If in chat mode, shutdown the socket server rather than Waitress.
+        if self.mode == "chat":
+            self.socketio.stop()
+
+        if self.waitress:
+            self.waitress_custom_shutdown()
 
     def cleanup(self):
         """
@@ -409,3 +394,14 @@ class Web:
             dir.cleanup()
 
         self.cleanup_tempdirs = []
+
+    def waitress_custom_shutdown(self):
+        """Shutdown the Waitress server immediately"""
+        # Code borrowed from https://github.com/Pylons/webtest/blob/4b8a3ebf984185ff4fefb31b4d0cf82682e1fcf7/webtest/http.py#L93-L104
+        while self.waitress._map:
+            triggers = list(self.waitress._map.values())
+            for trigger in triggers:
+                trigger.handle_close()
+        self.waitress.maintenance(0)
+        self.waitress.task_dispatcher.shutdown()
+        return True
diff --git a/cli/poetry.lock b/cli/poetry.lock
index 6c3f29c8..d4452ec1 100644
--- a/cli/poetry.lock
+++ b/cli/poetry.lock
@@ -1,4 +1,4 @@
-# This file is automatically @generated by Poetry and should not be changed by hand.
+# This file is automatically @generated by Poetry 1.5.0 and should not be changed by hand.
 
 [[package]]
 name = "bidict"
@@ -18,6 +18,110 @@ lint = ["pre-commit"]
 test = ["hypothesis", "pytest", "pytest-benchmark[histogram]", "pytest-cov", "pytest-xdist", "sortedcollections", "sortedcontainers", "sphinx"]
 
 [[package]]
+name = "blinker"
+version = "1.6.2"
+description = "Fast, simple object-to-object and broadcast signaling"
+category = "main"
+optional = false
+python-versions = ">=3.7"
+files = [
+    {file = "blinker-1.6.2-py3-none-any.whl", hash = "sha256:c3d739772abb7bc2860abf5f2ec284223d9ad5c76da018234f6f50d6f31ab1f0"},
+    {file = "blinker-1.6.2.tar.gz", hash = "sha256:4afd3de66ef3a9f8067559fb7a1cbe555c17dcbe15971b05d1b625c3e7abe213"},
+]
+
+[[package]]
+name = "brotli"
+version = "1.0.9"
+description = "Python bindings for the Brotli compression library"
+category = "main"
+optional = false
+python-versions = "*"
+files = [
+    {file = "Brotli-1.0.9-cp27-cp27m-macosx_10_9_x86_64.whl", hash = "sha256:268fe94547ba25b58ebc724680609c8ee3e5a843202e9a381f6f9c5e8bdb5c70"},
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+    {file = "Brotli-1.0.9-pp37-pypy37_pp73-macosx_10_9_x86_64.whl", hash = "sha256:9749a124280a0ada4187a6cfd1ffd35c350fb3af79c706589d98e088c5044267"},
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+    {file = "Brotli-1.0.9-pp37-pypy37_pp73-manylinux_2_5_x86_64.manylinux1_x86_64.manylinux_2_12_x86_64.manylinux2010_x86_64.whl", hash = "sha256:02177603aaca36e1fd21b091cb742bb3b305a569e2402f1ca38af471777fb019"},
+    {file = "Brotli-1.0.9-pp37-pypy37_pp73-win_amd64.whl", hash = "sha256:76ffebb907bec09ff511bb3acc077695e2c32bc2142819491579a695f77ffd4d"},
+    {file = "Brotli-1.0.9-pp38-pypy38_pp73-macosx_10_9_x86_64.whl", hash = "sha256:b43775532a5904bc938f9c15b77c613cb6ad6fb30990f3b0afaea82797a402d8"},
+    {file = "Brotli-1.0.9-pp38-pypy38_pp73-manylinux_2_5_i686.manylinux1_i686.manylinux_2_12_i686.manylinux2010_i686.whl", hash = "sha256:5bf37a08493232fbb0f8229f1824b366c2fc1d02d64e7e918af40acd15f3e337"},
+    {file = "Brotli-1.0.9-pp38-pypy38_pp73-manylinux_2_5_x86_64.manylinux1_x86_64.manylinux_2_12_x86_64.manylinux2010_x86_64.whl", hash = "sha256:330e3f10cd01da535c70d09c4283ba2df5fb78e915bea0a28becad6e2ac010be"},
+    {file = "Brotli-1.0.9-pp38-pypy38_pp73-win_amd64.whl", hash = "sha256:e1abbeef02962596548382e393f56e4c94acd286bd0c5afba756cffc33670e8a"},
+    {file = "Brotli-1.0.9-pp39-pypy39_pp73-macosx_10_9_x86_64.whl", hash = "sha256:3148362937217b7072cf80a2dcc007f09bb5ecb96dae4617316638194113d5be"},
+    {file = "Brotli-1.0.9-pp39-pypy39_pp73-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:336b40348269f9b91268378de5ff44dc6fbaa2268194f85177b53463d313842a"},
+    {file = "Brotli-1.0.9-pp39-pypy39_pp73-manylinux_2_5_i686.manylinux1_i686.manylinux_2_17_i686.manylinux2014_i686.whl", hash = "sha256:3b8b09a16a1950b9ef495a0f8b9d0a87599a9d1f179e2d4ac014b2ec831f87e7"},
+    {file = "Brotli-1.0.9-pp39-pypy39_pp73-win_amd64.whl", hash = "sha256:c8e521a0ce7cf690ca84b8cc2272ddaf9d8a50294fd086da67e517439614c755"},
+    {file = "Brotli-1.0.9.zip", hash = "sha256:4d1b810aa0ed773f81dceda2cc7b403d01057458730e309856356d4ef4188438"},
+]
+
+[[package]]
 name = "certifi"
 version = "2023.5.7"
 description = "Python package for providing Mozilla's CA Bundle."
@@ -273,27 +377,45 @@ test = ["pytest (>=6)"]
 
 [[package]]
 name = "flask"
-version = "2.0.3"
+version = "2.3.2"
 description = "A simple framework for building complex web applications."
 category = "main"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.8"
 files = [
-    {file = "Flask-2.0.3-py3-none-any.whl", hash = "sha256:59da8a3170004800a2837844bfa84d49b022550616070f7cb1a659682b2e7c9f"},
-    {file = "Flask-2.0.3.tar.gz", hash = "sha256:e1120c228ca2f553b470df4a5fa927ab66258467526069981b3eb0a91902687d"},
+    {file = "Flask-2.3.2-py3-none-any.whl", hash = "sha256:77fd4e1249d8c9923de34907236b747ced06e5467ecac1a7bb7115ae0e9670b0"},
+    {file = "Flask-2.3.2.tar.gz", hash = "sha256:8c2f9abd47a9e8df7f0c3f091ce9497d011dc3b31effcf4c85a6e2b50f4114ef"},
 ]
 
 [package.dependencies]
-click = ">=7.1.2"
-itsdangerous = ">=2.0"
-Jinja2 = ">=3.0"
-Werkzeug = ">=2.0"
+blinker = ">=1.6.2"
+click = ">=8.1.3"
+importlib-metadata = {version = ">=3.6.0", markers = "python_version < \"3.10\""}
+itsdangerous = ">=2.1.2"
+Jinja2 = ">=3.1.2"
+Werkzeug = ">=2.3.3"
 
 [package.extras]
 async = ["asgiref (>=3.2)"]
 dotenv = ["python-dotenv"]
 
 [[package]]
+name = "flask-compress"
+version = "1.13"
+description = "Compress responses in your Flask app with gzip, deflate or brotli."
+category = "main"
+optional = false
+python-versions = "*"
+files = [
+    {file = "Flask-Compress-1.13.tar.gz", hash = "sha256:ee96f18bf9b00f2deb4e3406ca4a05093aa80e2ef0578525a3b4d32ecdff129d"},
+    {file = "Flask_Compress-1.13-py3-none-any.whl", hash = "sha256:1128f71fbd788393ce26830c51f8b5a1a7a4d085e79a21a5cddf4c057dcd559b"},
+]
+
+[package.dependencies]
+brotli = "*"
+flask = "*"
+
+[[package]]
 name = "flask-socketio"
 version = "5.3.4"
 description = "Socket.IO integration for Flask applications"
@@ -487,6 +609,26 @@ files = [
 ]
 
 [[package]]
+name = "importlib-metadata"
+version = "6.6.0"
+description = "Read metadata from Python packages"
+category = "main"
+optional = false
+python-versions = ">=3.7"
+files = [
+    {file = "importlib_metadata-6.6.0-py3-none-any.whl", hash = "sha256:43dd286a2cd8995d5eaef7fee2066340423b818ed3fd70adf0bad5f1fac53fed"},
+    {file = "importlib_metadata-6.6.0.tar.gz", hash = "sha256:92501cdf9cc66ebd3e612f1b4f0c0765dfa42f0fa38ffb319b6bd84dd675d705"},
+]
+
+[package.dependencies]
+zipp = ">=0.5"
+
+[package.extras]
+docs = ["furo", "jaraco.packaging (>=9)", "jaraco.tidelift (>=1.4)", "rst.linker (>=1.9)", "sphinx (>=3.5)", "sphinx-lint"]
+perf = ["ipython"]
+testing = ["flake8 (<5)", "flufl.flake8", "importlib-resources (>=1.3)", "packaging", "pyfakefs", "pytest (>=6)", "pytest-black (>=0.3.7)", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-flake8", "pytest-mypy (>=0.9.1)", "pytest-perf (>=0.9.2)"]
+
+[[package]]
 name = "iniconfig"
 version = "2.0.0"
 description = "brain-dead simple config-ini parsing"
@@ -860,19 +1002,54 @@ socks = ["pysocks (>=1.5.6,!=1.5.7,<2.0)"]
 zstd = ["zstandard (>=0.18.0)"]
 
 [[package]]
+name = "waitress"
+version = "2.1.2"
+description = "Waitress WSGI server"
+category = "main"
+optional = false
+python-versions = ">=3.7.0"
+files = [
+    {file = "waitress-2.1.2-py3-none-any.whl", hash = "sha256:7500c9625927c8ec60f54377d590f67b30c8e70ef4b8894214ac6e4cad233d2a"},
+    {file = "waitress-2.1.2.tar.gz", hash = "sha256:780a4082c5fbc0fde6a2fcfe5e26e6efc1e8f425730863c04085769781f51eba"},
+]
+
+[package.extras]
+docs = ["Sphinx (>=1.8.1)", "docutils", "pylons-sphinx-themes (>=1.0.9)"]
+testing = ["coverage (>=5.0)", "pytest", "pytest-cover"]
+
+[[package]]
 name = "werkzeug"
-version = "2.0.3"
+version = "2.3.4"
 description = "The comprehensive WSGI web application library."
 category = "main"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.8"
+files = [
+    {file = "Werkzeug-2.3.4-py3-none-any.whl", hash = "sha256:48e5e61472fee0ddee27ebad085614ebedb7af41e88f687aaf881afb723a162f"},
+    {file = "Werkzeug-2.3.4.tar.gz", hash = "sha256:1d5a58e0377d1fe39d061a5de4469e414e78ccb1e1e59c0f5ad6fa1c36c52b76"},
+]
+
+[package.dependencies]
+MarkupSafe = ">=2.1.1"
+
+[package.extras]
+watchdog = ["watchdog (>=2.3)"]
+
+[[package]]
+name = "zipp"
+version = "3.15.0"
+description = "Backport of pathlib-compatible object wrapper for zip files"
+category = "main"
+optional = false
+python-versions = ">=3.7"
 files = [
-    {file = "Werkzeug-2.0.3-py3-none-any.whl", hash = "sha256:1421ebfc7648a39a5c58c601b154165d05cf47a3cd0ccb70857cbdacf6c8f2b8"},
-    {file = "Werkzeug-2.0.3.tar.gz", hash = "sha256:b863f8ff057c522164b6067c9e28b041161b4be5ba4d0daceeaa50a163822d3c"},
+    {file = "zipp-3.15.0-py3-none-any.whl", hash = "sha256:48904fc76a60e542af151aded95726c1a5c34ed43ab4134b597665c86d7ad556"},
+    {file = "zipp-3.15.0.tar.gz", hash = "sha256:112929ad649da941c23de50f356a2b5570c954b65150642bccdd66bf194d224b"},
 ]
 
 [package.extras]
-watchdog = ["watchdog"]
+docs = ["furo", "jaraco.packaging (>=9)", "jaraco.tidelift (>=1.4)", "rst.linker (>=1.9)", "sphinx (>=3.5)", "sphinx-lint"]
+testing = ["big-O", "flake8 (<5)", "jaraco.functools", "jaraco.itertools", "more-itertools", "pytest (>=6)", "pytest-black (>=0.3.7)", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-flake8", "pytest-mypy (>=0.9.1)"]
 
 [[package]]
 name = "zope-event"
@@ -944,4 +1121,4 @@ testing = ["coverage (>=5.0.3)", "zope.event", "zope.testing"]
 [metadata]
 lock-version = "2.0"
 python-versions = ">=3.8,<3.12"
-content-hash = "a66690a27977b5b8f8798846ff8a243639e7c425c38cd3426af646469ea5e5e3"
+content-hash = "a66690a27977b5b8f8798846ff8a243639e7c425c38cd3426af646469ea5e5e3"
\ No newline at end of file
diff --git a/cli/pyproject.toml b/cli/pyproject.toml
index 1da61878..f6ff9c94 100644
--- a/cli/pyproject.toml
+++ b/cli/pyproject.toml
@@ -18,7 +18,8 @@ classifiers = [
 [tool.poetry.dependencies]
 python = ">=3.8,<3.12"
 click = "*"
-flask = "2.0.3"
+flask = "2.3.2"
+flask-compress = "^1.13"
 flask-socketio = "5.3.4"
 psutil = "*"
 pysocks = "*"
@@ -31,7 +32,8 @@ pynacl = "*"
 colorama = "*"
 gevent-websocket = "*"
 stem = "1.8.1"
-werkzeug = "~2.0.3"
+waitress = "^2.1.2"
+werkzeug = ">=2.3.4"
 
 [tool.poetry.dev-dependencies]
 pytest = ">=7.2.0"
diff --git a/desktop/onionshare/gui_common.py b/desktop/onionshare/gui_common.py
index bb7e1f1b..e3d712f5 100644
--- a/desktop/onionshare/gui_common.py
+++ b/desktop/onionshare/gui_common.py
@@ -41,7 +41,7 @@ from onionshare_cli.onion import (
     PortNotAvailable,
 )
 from onionshare_cli.meek import Meek
-
+from onionshare_cli.web.web import WaitressException
 
 class GuiCommon:
     """
@@ -581,6 +581,13 @@ class GuiCommon:
             return strings._("error_port_not_available")
         return None
 
+    @staticmethod
+    def get_translated_web_error(e):
+        """
+        Takes an exception defined in web.py and returns a translated error message
+        """
+        if type(e) is WaitressException:
+            return strings._("waitress_web_server_error")
 
 class ToggleCheckbox(QtWidgets.QCheckBox):
     def __init__(self, text):
diff --git a/desktop/onionshare/resources/locale/en.json b/desktop/onionshare/resources/locale/en.json
index 5dfb831e..c9e6d86a 100644
--- a/desktop/onionshare/resources/locale/en.json
+++ b/desktop/onionshare/resources/locale/en.json
@@ -252,5 +252,6 @@
     "moat_bridgedb_error": "Could not contact BridgeDB.",
     "moat_captcha_error": "Incorrect solution. Please try again.",
     "moat_solution_empty_error": "Enter the characters from the image",
-    "mode_tor_not_connected_label": "OnionShare is not connected to the Tor network"
+    "mode_tor_not_connected_label": "OnionShare is not connected to the Tor network",
+    "waitress_web_server_error": "There was a problem starting the web server"
 }
diff --git a/desktop/onionshare/tab/mode/__init__.py b/desktop/onionshare/tab/mode/__init__.py
index 27958d84..34d78cbd 100644
--- a/desktop/onionshare/tab/mode/__init__.py
+++ b/desktop/onionshare/tab/mode/__init__.py
@@ -27,7 +27,7 @@ from .mode_settings_widget import ModeSettingsWidget
 
 from ..server_status import ServerStatus
 from ... import strings
-from ...threads import OnionThread, AutoStartTimer
+from ...threads import OnionThread, WebThread, AutoStartTimer
 from ...widgets import Alert, MinimumSizeWidget
 
 
@@ -294,6 +294,8 @@ class Mode(QtWidgets.QWidget):
             self.onion_thread.success.connect(self.starting_server_step2.emit)
             self.onion_thread.success_early.connect(self.starting_server_early.emit)
             self.onion_thread.error.connect(self.starting_server_error.emit)
+            self.web_thread = WebThread(self)
+            self.web_thread.error.connect(self.starting_server_error.emit)
             self.onion_thread.start()
 
     def start_scheduled_service(self, obtain_onion_early=False):
diff --git a/desktop/onionshare/threads.py b/desktop/onionshare/threads.py
index db0c6145..6eeeb97f 100644
--- a/desktop/onionshare/threads.py
+++ b/desktop/onionshare/threads.py
@@ -39,6 +39,8 @@ from onionshare_cli.onion import (
     PortNotAvailable,
 )
 
+from onionshare_cli.web.web import WaitressException
+
 from . import strings
 
 
@@ -62,9 +64,6 @@ class OnionThread(QtCore.QThread):
     def run(self):
         self.mode.common.log("OnionThread", "run")
 
-        # Make a new static URL path for each new share
-        self.mode.web.generate_static_url_path()
-
         # Choose port early, because we need them to exist in advance for scheduled shares
         if not self.mode.app.port:
             self.mode.app.choose_port()
@@ -86,7 +85,6 @@ class OnionThread(QtCore.QThread):
                 # wait for modules in thread to load, preventing a thread-related cx_Freeze crash
                 time.sleep(0.2)
                 # start onionshare http service in new thread
-                self.mode.web_thread = WebThread(self.mode)
                 self.mode.web_thread.start()
                 self.success.emit()
 
@@ -125,9 +123,14 @@ class WebThread(QtCore.QThread):
 
     def run(self):
         self.mode.common.log("WebThread", "run")
-        self.mode.web.start(self.mode.app.port)
-        self.success.emit()
-
+        try:
+            self.mode.web.start(self.mode.app.port)
+            self.success.emit()
+        except WaitressException as e:
+            message = self.mode.common.gui.get_translated_web_error(e)
+            self.mode.common.log("WebThread", "run", message)
+            self.error.emit(message)
+            return
 
 class AutoStartTimer(QtCore.QThread):
     """
diff --git a/desktop/poetry.lock b/desktop/poetry.lock
index 581513de..ba2728fe 100644
--- a/desktop/poetry.lock
+++ b/desktop/poetry.lock
@@ -1,4 +1,4 @@
-# This file is automatically @generated by Poetry and should not be changed by hand.
+# This file is automatically @generated by Poetry 1.5.0 and should not be changed by hand.
 
 [[package]]
 name = "bidict"
@@ -20,8 +20,8 @@ test = ["hypothesis", "pytest", "pytest-benchmark[histogram]", "pytest-cov", "py
 [[package]]
 name = "black"
 version = "23.3.0"
-description = "The uncompromising code formatter."
 category = "dev"
+description = "The uncompromising code formatter."
 optional = false
 python-versions = ">=3.7"
 files = [
@@ -68,6 +68,110 @@ jupyter = ["ipython (>=7.8.0)", "tokenize-rt (>=3.2.0)"]
 uvloop = ["uvloop (>=0.15.2)"]
 
 [[package]]
+name = "blinker"
+version = "1.6.2"
+description = "Fast, simple object-to-object and broadcast signaling"
+category = "main"
+optional = false
+python-versions = ">=3.7"
+files = [
+    {file = "blinker-1.6.2-py3-none-any.whl", hash = "sha256:c3d739772abb7bc2860abf5f2ec284223d9ad5c76da018234f6f50d6f31ab1f0"},
+    {file = "blinker-1.6.2.tar.gz", hash = "sha256:4afd3de66ef3a9f8067559fb7a1cbe555c17dcbe15971b05d1b625c3e7abe213"},
+]
+
+[[package]]
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 [package.dependencies]
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 patchelf = [
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+    {version = ">=0.14", markers = "sys_platform == \"linux\" and (platform_machine == \"aarch64\" or platform_machine == \"i686\" or platform_machine == \"ppc64le\" or platform_machine == \"s390x\" or platform_machine == \"x86_64\")"},
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 ]
 setuptools = ">=62.6,<68"
 
 [package.extras]
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-test = ["nose (==1.3.7)", "pygments (>=2.13.0)", "pytest (>=7.1.3)", "pytest-cov (>=4.0.0)", "pytest-mock (>=3.10.0)", "pytest-timeout (>=2.1.0)"]
+dev = ["bump2version (==1.0.1)", "cibuildwheel (==2.12.3)", "pre-commit (>=2.21.0)", "pylint (==2.17.4)", "wheel (==0.40.0)"]
+doc = ["furo (==2023.3.27)", "sphinx (==5.3.0)", "sphinx-tabs (==3.4.1)"]
+test = ["nose (==1.3.7)", "pygments (==2.15.1)", "pytest (==7.3.1)", "pytest-cov (==4.0.0)", "pytest-mock (==3.10.0)", "pytest-timeout (==2.1.0)"]
 
 [[package]]
 name = "cx-logging"
@@ -420,36 +524,54 @@ test = ["pytest (>=6)"]
 
 [[package]]
 name = "flask"
-version = "2.0.3"
+version = "2.3.2"
 description = "A simple framework for building complex web applications."
 category = "main"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.8"
 files = [
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 ]
 
 [package.dependencies]
-click = ">=7.1.2"
-itsdangerous = ">=2.0"
-Jinja2 = ">=3.0"
-Werkzeug = ">=2.0"
+blinker = ">=1.6.2"
+click = ">=8.1.3"
+importlib-metadata = {version = ">=3.6.0", markers = "python_version < \"3.10\""}
+itsdangerous = ">=2.1.2"
+Jinja2 = ">=3.1.2"
+Werkzeug = ">=2.3.3"
 
 [package.extras]
 async = ["asgiref (>=3.2)"]
 dotenv = ["python-dotenv"]
 
 [[package]]
+name = "flask-compress"
+version = "1.13"
+description = "Compress responses in your Flask app with gzip, deflate or brotli."
+category = "main"
+optional = false
+python-versions = "*"
+files = [
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+]
+
+[package.dependencies]
+brotli = "*"
+flask = "*"
+
+[[package]]
 name = "flask-socketio"
-version = "5.3.1"
+version = "5.3.4"
 description = "Socket.IO integration for Flask applications"
 category = "main"
 optional = false
 python-versions = ">=3.6"
 files = [
-    {file = "Flask-SocketIO-5.3.1.tar.gz", hash = "sha256:fd0ed0fc1341671d92d5f5b2f5503916deb7aa7e2940e6636cfa2c087c828bf9"},
-    {file = "Flask_SocketIO-5.3.1-py3-none-any.whl", hash = "sha256:ff0c721f20bff1e2cfba77948727a8db48f187e89a72fe50c34478ce6efb3353"},
+    {file = "Flask-SocketIO-5.3.4.tar.gz", hash = "sha256:1cbd379c9bf68ac37bcc4750d01708922fa6365d13a5447d3f8893792879410c"},
+    {file = "Flask_SocketIO-5.3.4-py3-none-any.whl", hash = "sha256:564acfb24dcc9545cdae536cde0323653d9b547069a925f11eeb132338aa71c0"},
 ]
 
 [package.dependencies]
@@ -637,7 +759,7 @@ files = [
 name = "importlib-metadata"
 version = "6.6.0"
 description = "Read metadata from Python packages"
-category = "dev"
+category = "main"
 optional = false
 python-versions = ">=3.7"
 files = [
@@ -697,35 +819,35 @@ i18n = ["Babel (>=2.7)"]
 
 [[package]]
 name = "lief"
-version = "0.13.0"
+version = "0.13.1"
 description = "Library to instrument executable formats"
 category = "dev"
 optional = false
 python-versions = ">=3.8"
 files = [
-    {file = "lief-0.13.0-cp310-cp310-macosx_10_14_x86_64.whl", hash = "sha256:e573bf1e37cd580ef87243d0dc48d5c56d535b84a8c91b9fa28f9631643cdc51"},
-    {file = "lief-0.13.0-cp310-cp310-macosx_11_0_arm64.whl", hash = "sha256:c49aa1e573ddf7d9946d9779b5f4edad782976368c15094c6a815533fc1b50fd"},
-    {file = "lief-0.13.0-cp310-cp310-manylinux2014_aarch64.whl", hash = "sha256:0740eb7b2093ed82570315d614671ad69cc21a062d73e9213a263eec7c11dc3a"},
-    {file = "lief-0.13.0-cp310-cp310-manylinux_2_24_x86_64.whl", hash = "sha256:c072929606f621697c9da2fabefccf8dac47a4283b8988ae9b3f6ca332352d66"},
-    {file = "lief-0.13.0-cp310-cp310-win32.whl", hash = "sha256:6c74fe1684f859a041408d6fc4c6262686bfb74d64afe38f7373c173fd144ac5"},
-    {file = "lief-0.13.0-cp310-cp310-win_amd64.whl", hash = "sha256:9f562a07f6fc4dc7958943fe840755932ffaf10da500ab1a537004ab61f6d3de"},
-    {file = "lief-0.13.0-cp311-cp311-macosx_10_14_x86_64.whl", hash = "sha256:8740abb2c0fb38a5040f4559a3766b724228a97155e92aa8cc8fa01bef1cea83"},
-    {file = "lief-0.13.0-cp311-cp311-macosx_11_0_arm64.whl", hash = "sha256:9daf09130edf02ca47b76f0b98390aa618b3d3bbc9c0588250b738ef50f4a539"},
-    {file = "lief-0.13.0-cp311-cp311-manylinux2014_aarch64.whl", hash = "sha256:41ad87a7233927fef40c6b7e60684b962e623ef21d28be3528c9bd943be710b7"},
-    {file = "lief-0.13.0-cp311-cp311-manylinux_2_24_x86_64.whl", hash = "sha256:cacf8097970ddd5bbb82a6ad5c02f0423767300a3457d84566643cf3c4d7a69f"},
-    {file = "lief-0.13.0-cp311-cp311-win32.whl", hash = "sha256:07986f0991e1f942d4a277e4b15fe37dbc5b2a54c3baf2a58e719d9b258ce810"},
-    {file = "lief-0.13.0-cp311-cp311-win_amd64.whl", hash = "sha256:31825961aa778481e483dcb081a40daec3dfa78ca8b2a4acefc32040ce4886ad"},
-    {file = "lief-0.13.0-cp38-cp38-macosx_10_14_x86_64.whl", hash = "sha256:c91e389604f4689d1de712b003d0df2ff9d3f47fd71e1bd4f1b36692a34ed97d"},
-    {file = "lief-0.13.0-cp38-cp38-manylinux2014_aarch64.whl", hash = "sha256:379201222ba63ac62399eabe7c97de0bbe5736f2f72c000cc224ebe6724b4bab"},
-    {file = "lief-0.13.0-cp38-cp38-manylinux_2_24_x86_64.whl", hash = "sha256:e1b292730658941035ea997de0fd6bd65393c660fe3a2afb53d737e6c4a156e4"},
-    {file = "lief-0.13.0-cp38-cp38-win32.whl", hash = "sha256:e744f3523913a1101af34c71e1c10a14a5c50eaaf054a53d469df19070e980d6"},
-    {file = "lief-0.13.0-cp38-cp38-win_amd64.whl", hash = "sha256:e15fabc5c86ebad7300c8eed1dcecb0a20e9fd4669b304192625edbb34b6e7f3"},
-    {file = "lief-0.13.0-cp39-cp39-macosx_10_14_x86_64.whl", hash = "sha256:15c3e128d8c4ef9ba0f2d890003836e874ab285c5c09139df73fa4aef8abe70d"},
-    {file = "lief-0.13.0-cp39-cp39-macosx_11_0_arm64.whl", hash = "sha256:f453f70c3c19f1d24008ae7d2aee4de3b2d73d095b99db78a062288c7ff6232b"},
-    {file = "lief-0.13.0-cp39-cp39-manylinux2014_aarch64.whl", hash = "sha256:456e162c5cf518b34763f1a3c849a4af0a16d6b603729930064679b2756e8710"},
-    {file = "lief-0.13.0-cp39-cp39-manylinux_2_24_x86_64.whl", hash = "sha256:28e15c164f49e66a6a876a12662414592f43444175d4fa9aad8d55654f4515af"},
-    {file = "lief-0.13.0-cp39-cp39-win32.whl", hash = "sha256:2cfd8496ac85b64569a07f4cdd1e7424039e24113bdebc9ecc99694a8cf856f7"},
-    {file = "lief-0.13.0-cp39-cp39-win_amd64.whl", hash = "sha256:70b08135413abe034e11c7c931de29be3e1902dde717c0681623da4fa18a3714"},
+    {file = "lief-0.13.1-cp310-cp310-macosx_10_14_x86_64.whl", hash = "sha256:b53317d78f8b7528e3f2f358b3f9334a1a84fae88c5aec1a3b7717ed31bfb066"},
+    {file = "lief-0.13.1-cp310-cp310-macosx_11_0_arm64.whl", hash = "sha256:bb8b285a6c670df590c36fc0c19b9d2e32b99f17e57afa29bb3052f1d55aa50f"},
+    {file = "lief-0.13.1-cp310-cp310-manylinux2014_aarch64.whl", hash = "sha256:be871116faa698b6d9da76b0caec2ec5b7e7b8781cfb3a4ac0c4e348fb37ab49"},
+    {file = "lief-0.13.1-cp310-cp310-manylinux_2_24_x86_64.whl", hash = "sha256:c6839df875e912edd3fc553ab5d1b916527adee9c57ba85c69314a93f7ba2e15"},
+    {file = "lief-0.13.1-cp310-cp310-win32.whl", hash = "sha256:b1f295dbb57094443926ac6051bee9a1945d92344f470da1cb506060eb2f91ac"},
+    {file = "lief-0.13.1-cp310-cp310-win_amd64.whl", hash = "sha256:8439805a389cc67b6d4ea7d757a3211f22298edce53c5b064fdf8bf05fabba54"},
+    {file = "lief-0.13.1-cp311-cp311-macosx_10_14_x86_64.whl", hash = "sha256:3cfbc6c50f9e3a8015cd5ee88dfe83f423562c025439143bbd5c086a3f9fe599"},
+    {file = "lief-0.13.1-cp311-cp311-macosx_11_0_arm64.whl", hash = "sha256:661abaa48bc032b9a7529e0b73d2ced3e4a1f13381592f6b9e940750b07a5ac2"},
+    {file = "lief-0.13.1-cp311-cp311-manylinux2014_aarch64.whl", hash = "sha256:23617d96d162081f8bf315d9b0494845891f8d0f04ad60991b83367ee9e261aa"},
+    {file = "lief-0.13.1-cp311-cp311-manylinux_2_24_x86_64.whl", hash = "sha256:aa7f45c5125be80a513624d3a5f6bd50751c2edc6de5357fde218580111c8535"},
+    {file = "lief-0.13.1-cp311-cp311-win32.whl", hash = "sha256:018b542f09fe2305e1585a3e63a7e5132927b835062b456e5c8c571db7784d1e"},
+    {file = "lief-0.13.1-cp311-cp311-win_amd64.whl", hash = "sha256:bfbf8885a3643ea9aaf663d039f50ca58b228886c3fe412725b22851aeda3b77"},
+    {file = "lief-0.13.1-cp38-cp38-macosx_10_14_x86_64.whl", hash = "sha256:a0472636ab15b9afecf8b5d55966912af8cb4de2f05b98fc05c87d51880d0208"},
+    {file = "lief-0.13.1-cp38-cp38-manylinux2014_aarch64.whl", hash = "sha256:ccfba33c02f21d4ede26ab85eb6539a00e74e236569c13dcbab2e157b73673c4"},
+    {file = "lief-0.13.1-cp38-cp38-manylinux_2_24_x86_64.whl", hash = "sha256:e414d6c23f26053f4824d080885ab1b75482122796cba7d09cbf157900646289"},
+    {file = "lief-0.13.1-cp38-cp38-win32.whl", hash = "sha256:a18fee5cf69adf9d5ee977778ccd46c39c450960f806231b26b69011f81bc712"},
+    {file = "lief-0.13.1-cp38-cp38-win_amd64.whl", hash = "sha256:04c87039d1e68ebc467f83136179626403547dd1ce851541345f8ca0b1fe6c5b"},
+    {file = "lief-0.13.1-cp39-cp39-macosx_10_14_x86_64.whl", hash = "sha256:0283a4c749afe58be8e21cdd9be79c657c51ca9b8346f75f4b97349b1f022851"},
+    {file = "lief-0.13.1-cp39-cp39-macosx_11_0_arm64.whl", hash = "sha256:95a4b6d1f8dba9360aecf7542e54ce5eb02c0e88f2d827b5445594d5d51109f5"},
+    {file = "lief-0.13.1-cp39-cp39-manylinux2014_aarch64.whl", hash = "sha256:16753bd72b1e3932d94d088a93b64e08c1f6c8bce1b064b47fe66ed73d9562b2"},
+    {file = "lief-0.13.1-cp39-cp39-manylinux_2_24_x86_64.whl", hash = "sha256:965fadb1301d1a81f16067e4fa743d2be3f6aa71391a83b752ff811ec74b0766"},
+    {file = "lief-0.13.1-cp39-cp39-win32.whl", hash = "sha256:57bdb0471760c4ff520f5e5d005e503cc7ea3ebe22df307bb579a1a561b8c4e9"},
+    {file = "lief-0.13.1-cp39-cp39-win_amd64.whl", hash = "sha256:a3c900f49c3d3135c728faeb386d13310bb3511eb2d4e1c9b109b48ae2658361"},
 ]
 
 [[package]]
@@ -814,8 +936,9 @@ develop = true
 click = "*"
 colorama = "*"
 eventlet = "*"
-flask = "2.0.3"
-flask-socketio = "5.3.1"
+flask = "2.3.2"
+flask-compress = "^1.13"
+flask-socketio = "5.3.4"
 gevent-websocket = "*"
 psutil = "*"
 pynacl = "*"
@@ -825,7 +948,8 @@ setuptools = "*"
 stem = "1.8.1"
 unidecode = "*"
 urllib3 = "*"
-werkzeug = "~2.0.3"
+waitress = "^2.1.2"
+werkzeug = ">=2.3.4"
 
 [package.source]
 type = "directory"
@@ -1189,14 +1313,14 @@ test = ["coverage", "pytest"]
 
 [[package]]
 name = "requests"
-version = "2.30.0"
+version = "2.31.0"
 description = "Python HTTP for Humans."
 category = "main"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "requests-2.30.0-py3-none-any.whl", hash = "sha256:10e94cc4f3121ee6da529d358cdaeaff2f1c409cd377dbc72b825852f2f7e294"},
-    {file = "requests-2.30.0.tar.gz", hash = "sha256:239d7d4458afcb28a692cdd298d87542235f4ca8d36d03a15bfc128a6559a2f4"},
+    {file = "requests-2.31.0-py3-none-any.whl", hash = "sha256:58cd2187c01e70e6e26505bca751777aa9f2ee0b7f4300988b709f44e013003f"},
+    {file = "requests-2.31.0.tar.gz", hash = "sha256:942c5a758f98d790eaed1a29cb6eefc7ffb0d1cf7af05c3d2791656dbd6ad1e1"},
 ]
 
 [package.dependencies]
@@ -1280,14 +1404,14 @@ files = [
 
 [[package]]
 name = "typing-extensions"
-version = "4.5.0"
+version = "4.6.2"
 description = "Backported and Experimental Type Hints for Python 3.7+"
 category = "main"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "typing_extensions-4.5.0-py3-none-any.whl", hash = "sha256:fb33085c39dd998ac16d1431ebc293a8b3eedd00fd4a32de0ff79002c19511b4"},
-    {file = "typing_extensions-4.5.0.tar.gz", hash = "sha256:5cb5f4a79139d699607b3ef622a1dedafa84e115ab0024e0d9c044a9479ca7cb"},
+    {file = "typing_extensions-4.6.2-py3-none-any.whl", hash = "sha256:3a8b36f13dd5fdc5d1b16fe317f5668545de77fa0b8e02006381fd49d731ab98"},
+    {file = "typing_extensions-4.6.2.tar.gz", hash = "sha256:06006244c70ac8ee83fa8282cb188f697b8db25bc8b4df07be1873c43897060c"},
 ]
 
 [[package]]
@@ -1321,25 +1445,44 @@ socks = ["pysocks (>=1.5.6,!=1.5.7,<2.0)"]
 zstd = ["zstandard (>=0.18.0)"]
 
 [[package]]
+name = "waitress"
+version = "2.1.2"
+description = "Waitress WSGI server"
+category = "main"
+optional = false
+python-versions = ">=3.7.0"
+files = [
+    {file = "waitress-2.1.2-py3-none-any.whl", hash = "sha256:7500c9625927c8ec60f54377d590f67b30c8e70ef4b8894214ac6e4cad233d2a"},
+    {file = "waitress-2.1.2.tar.gz", hash = "sha256:780a4082c5fbc0fde6a2fcfe5e26e6efc1e8f425730863c04085769781f51eba"},
+]
+
+[package.extras]
+docs = ["Sphinx (>=1.8.1)", "docutils", "pylons-sphinx-themes (>=1.0.9)"]
+testing = ["coverage (>=5.0)", "pytest", "pytest-cover"]
+
+[[package]]
 name = "werkzeug"
-version = "2.0.3"
+version = "2.3.4"
 description = "The comprehensive WSGI web application library."
 category = "main"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.8"
 files = [
-    {file = "Werkzeug-2.0.3-py3-none-any.whl", hash = "sha256:1421ebfc7648a39a5c58c601b154165d05cf47a3cd0ccb70857cbdacf6c8f2b8"},
-    {file = "Werkzeug-2.0.3.tar.gz", hash = "sha256:b863f8ff057c522164b6067c9e28b041161b4be5ba4d0daceeaa50a163822d3c"},
+    {file = "Werkzeug-2.3.4-py3-none-any.whl", hash = "sha256:48e5e61472fee0ddee27ebad085614ebedb7af41e88f687aaf881afb723a162f"},
+    {file = "Werkzeug-2.3.4.tar.gz", hash = "sha256:1d5a58e0377d1fe39d061a5de4469e414e78ccb1e1e59c0f5ad6fa1c36c52b76"},
 ]
 
+[package.dependencies]
+MarkupSafe = ">=2.1.1"
+
 [package.extras]
-watchdog = ["watchdog"]
+watchdog = ["watchdog (>=2.3)"]
 
 [[package]]
 name = "zipp"
 version = "3.15.0"
 description = "Backport of pathlib-compatible object wrapper for zip files"
-category = "dev"
+category = "main"
 optional = false
 python-versions = ">=3.7"
 files = [
@@ -1421,4 +1564,4 @@ testing = ["coverage (>=5.0.3)", "zope.event", "zope.testing"]
 [metadata]
 lock-version = "2.0"
 python-versions = ">=3.8,<3.12"
-content-hash = "2710a16bd208be80681f3166ab54e989baf10291105c967c44ee55c2f57bd710"
+content-hash = "6611e6f2177f7fd0ab1fea969add7b3270afc185a8fd857c561154d64d3cfc72"
diff --git a/desktop/pyproject.toml b/desktop/pyproject.toml
index 0096e50a..255cd73c 100644
--- a/desktop/pyproject.toml
+++ b/desktop/pyproject.toml
@@ -10,15 +10,15 @@ python = ">=3.8,<3.12"
 onionshare_cli = {path = "../cli", develop = true}
 PySide6 = "6.5.0"
 qrcode = "*"
-werkzeug = "~2.0.3"
-python-gnupg = "^0.5.0"
+werkzeug = "*"
+python-gnupg = "*"
 
 [tool.poetry.dev-dependencies]
 click = "*"
 black = "*"
-pytest = ">=7.2.0"
+pytest = "*"
 pytest-faulthandler = "*"
-pytest-qt = ">=4.2.0"
+pytest-qt = "*"
 cx_freeze = "*"
 importlib-metadata = "*"
 
diff --git a/desktop/tests/gui_base_test.py b/desktop/tests/gui_base_test.py
index 9180348d..af391a0d 100644
--- a/desktop/tests/gui_base_test.py
+++ b/desktop/tests/gui_base_test.py
@@ -58,6 +58,13 @@ class GuiBaseTest(unittest.TestCase):
                 "<html><body><p>This is a test website hosted by OnionShare</p></body></html>"
             )
 
+        # A file called "test.html"
+        cls.tmpfile_test_html = os.path.join(cls.tmpdir.name, "test.html")
+        with open(cls.tmpfile_test_html, "w") as file:
+            file.write(
+                "<html><body><p>Sed ut perspiciatis unde omnis iste natus error sit voluptatem accusantium doloremque laudantium, totam rem aperiam, eaque ipsa quae ab illo inventore veritatis et quasi architecto beatae vitae dicta sunt explicabo. Nemo enim ipsam voluptatem quia voluptas sit aspernatur aut odit aut fugit, sed quia consequuntur magni dolores eos qui ratione voluptatem sequi nesciunt. Neque porro quisquam est, qui dolorem ipsum quia dolor sit amet, consectetur, adipisci velit, sed quia non numquam eius modi tempora incidunt ut labore et dolore magnam aliquam quaerat voluptatem. Ut enim ad minima veniam, quis nostrum exercitationem ullam corporis suscipit laboriosam, nisi ut aliquid ex ea commodi consequatur? Quis autem vel eum iure reprehenderit qui in ea voluptate velit esse quam nihil molestiae consequatur, vel illum qui dolorem eum fugiat quo voluptas nulla pariatur?</p></body></html>"
+            )
+
         # A large file
         size = 1024 * 1024 * 155
         cls.tmpfile_large = os.path.join(cls.tmpdir.name, "large_file")
diff --git a/desktop/tests/test_gui_share.py b/desktop/tests/test_gui_share.py
index 02d50e4b..f0c460f2 100644
--- a/desktop/tests/test_gui_share.py
+++ b/desktop/tests/test_gui_share.py
@@ -541,3 +541,30 @@ class TestShare(GuiBaseTest):
         self.hit_405(url, expected_resp="OnionShare: 405 Method Not Allowed", data = {'foo':'bar'}, methods = ["put", "post", "delete", "options"])
         self.history_widgets_present(tab)
         self.close_all_tabs()
+
+
+    def test_compression(self):
+        """
+        A file with a compressable mimetype should return a Content-Encoding header
+        with gzip compression enabled.
+        """
+        tab = self.new_share_tab()
+        tab.get_mode().autostop_sharing_checkbox.click()
+
+        self.run_all_common_setup_tests()
+        self.run_all_share_mode_setup_tests(tab)
+        tab.get_mode().mode_settings_widget.public_checkbox.click()
+        tab.get_mode().remove_all_button.click()
+        tab.get_mode().server_status.file_selection.file_list.add_file(
+            self.tmpfile_test_html
+        )
+        self.run_all_share_mode_started_tests(tab)
+        url = f"http://127.0.0.1:{tab.app.port}/test.html"
+        r = requests.get(url)
+        self.assertTrue("Content-Encoding" in r.headers)
+        self.assertEqual("gzip", r.headers["Content-Encoding"])
+
+        self.server_is_stopped(tab)
+        self.web_server_is_stopped(tab)
+        self.server_status_indicator_says_closed(tab)
+        self.close_all_tabs()
diff --git a/docs/poetry.lock b/docs/poetry.lock
index 912c1d2a..08173fd5 100644
--- a/docs/poetry.lock
+++ b/docs/poetry.lock
@@ -1,18 +1,28 @@
+# This file is automatically @generated by Poetry and should not be changed by hand.
+
 [[package]]
 name = "alabaster"
-version = "0.7.12"
+version = "0.7.13"
 description = "A configurable sidebar-enabled Sphinx theme"
 category = "main"
 optional = false
-python-versions = "*"
+python-versions = ">=3.6"
+files = [
+    {file = "alabaster-0.7.13-py3-none-any.whl", hash = "sha256:1ee19aca801bbabb5ba3f5f258e4422dfa86f82f3e9cefb0859b283cdd7f62a3"},
+    {file = "alabaster-0.7.13.tar.gz", hash = "sha256:a27a4a084d5e690e16e01e03ad2b2e552c61a65469419b907243193de1a84ae2"},
+]
 
 [[package]]
 name = "anyio"
-version = "3.6.1"
+version = "3.6.2"
 description = "High level compatibility layer for multiple asynchronous event loop implementations"
 category = "main"
 optional = false
 python-versions = ">=3.6.2"
+files = [
+    {file = "anyio-3.6.2-py3-none-any.whl", hash = "sha256:fbbe32bd270d2a2ef3ed1c5d45041250284e31fc0a4df4a5a6071842051a51e3"},
+    {file = "anyio-3.6.2.tar.gz", hash = "sha256:25ea0d673ae30af41a0c442f81cf3b38c7e79fdc7b60335a4c14e05eb0947421"},
+]
 
 [package.dependencies]
 idna = ">=2.8"
@@ -21,37 +31,116 @@ sniffio = ">=1.1"
 [package.extras]
 doc = ["packaging", "sphinx-autodoc-typehints (>=1.2.0)", "sphinx-rtd-theme"]
 test = ["contextlib2", "coverage[toml] (>=4.5)", "hypothesis (>=4.0)", "mock (>=4)", "pytest (>=7.0)", "pytest-mock (>=3.6.1)", "trustme", "uvloop (<0.15)", "uvloop (>=0.15)"]
-trio = ["trio (>=0.16)"]
+trio = ["trio (>=0.16,<0.22)"]
 
 [[package]]
-name = "Babel"
-version = "2.10.3"
+name = "babel"
+version = "2.12.1"
 description = "Internationalization utilities"
 category = "main"
 optional = false
-python-versions = ">=3.6"
-
-[package.dependencies]
-pytz = ">=2015.7"
+python-versions = ">=3.7"
+files = [
+    {file = "Babel-2.12.1-py3-none-any.whl", hash = "sha256:b4246fb7677d3b98f501a39d43396d3cafdc8eadb045f4a31be01863f655c610"},
+    {file = "Babel-2.12.1.tar.gz", hash = "sha256:cc2d99999cd01d44420ae725a21c9e3711b3aadc7976d6147f622d8581963455"},
+]
 
 [[package]]
 name = "certifi"
-version = "2022.12.7"
+version = "2023.5.7"
 description = "Python package for providing Mozilla's CA Bundle."
 category = "main"
 optional = false
 python-versions = ">=3.6"
+files = [
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+]
 
 [[package]]
 name = "charset-normalizer"
-version = "2.1.1"
+version = "3.1.0"
 description = "The Real First Universal Charset Detector. Open, modern and actively maintained alternative to Chardet."
 category = "main"
 optional = false
-python-versions = ">=3.6.0"
-
-[package.extras]
-unicode_backport = ["unicodedata2"]
+python-versions = ">=3.7.0"
+files = [
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+]
 
 [[package]]
 name = "click"
@@ -60,46 +149,66 @@ description = "Composable command line interface toolkit"
 category = "main"
 optional = false
 python-versions = ">=3.7"
+files = [
+    {file = "click-8.1.3-py3-none-any.whl", hash = "sha256:bb4d8133cb15a609f44e8213d9b391b0809795062913b383c62be0ee95b1db48"},
+    {file = "click-8.1.3.tar.gz", hash = "sha256:7682dc8afb30297001674575ea00d1814d808d6a36af415a82bd481d37ba7b8e"},
+]
 
 [package.dependencies]
 colorama = {version = "*", markers = "platform_system == \"Windows\""}
 
 [[package]]
 name = "colorama"
-version = "0.4.5"
+version = "0.4.6"
 description = "Cross-platform colored terminal text."
 category = "main"
 optional = false
-python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*"
+python-versions = "!=3.0.*,!=3.1.*,!=3.2.*,!=3.3.*,!=3.4.*,!=3.5.*,!=3.6.*,>=2.7"
+files = [
+    {file = "colorama-0.4.6-py2.py3-none-any.whl", hash = "sha256:4f1d9991f5acc0ca119f9d443620b77f9d6b33703e51011c16baf57afb285fc6"},
+    {file = "colorama-0.4.6.tar.gz", hash = "sha256:08695f5cb7ed6e0531a20572697297273c47b8cae5a63ffc6d6ed5c201be6e44"},
+]
 
 [[package]]
 name = "docutils"
-version = "0.17.1"
+version = "0.18.1"
 description = "Docutils -- Python Documentation Utilities"
 category = "main"
 optional = false
 python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*"
+files = [
+    {file = "docutils-0.18.1-py2.py3-none-any.whl", hash = "sha256:23010f129180089fbcd3bc08cfefccb3b890b0050e1ca00c867036e9d161b98c"},
+    {file = "docutils-0.18.1.tar.gz", hash = "sha256:679987caf361a7539d76e584cbeddc311e3aee937877c87346f31debc63e9d06"},
+]
 
 [[package]]
 name = "h11"
-version = "0.12.0"
+version = "0.14.0"
 description = "A pure-Python, bring-your-own-I/O implementation of HTTP/1.1"
 category = "main"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.7"
+files = [
+    {file = "h11-0.14.0-py3-none-any.whl", hash = "sha256:e3fe4ac4b851c468cc8363d500db52c2ead036020723024a109d37346efaa761"},
+    {file = "h11-0.14.0.tar.gz", hash = "sha256:8f19fbbe99e72420ff35c00b27a34cb9937e902a8b810e2c88300c6f0a3b699d"},
+]
 
 [[package]]
 name = "httpcore"
-version = "0.15.0"
+version = "0.17.1"
 description = "A minimal low-level HTTP client."
 category = "main"
 optional = false
 python-versions = ">=3.7"
+files = [
+    {file = "httpcore-0.17.1-py3-none-any.whl", hash = "sha256:628e768aaeec1f7effdc6408ba1c3cdbd7487c1fc570f7d66844ec4f003e1ca4"},
+    {file = "httpcore-0.17.1.tar.gz", hash = "sha256:caf508597c525f9b8bfff187e270666309f63115af30f7d68b16143a403c8356"},
+]
 
 [package.dependencies]
-anyio = ">=3.0.0,<4.0.0"
+anyio = ">=3.0,<5.0"
 certifi = "*"
-h11 = ">=0.11,<0.13"
+h11 = ">=0.13,<0.15"
 sniffio = ">=1.0.0,<2.0.0"
 
 [package.extras]
@@ -108,21 +217,25 @@ socks = ["socksio (>=1.0.0,<2.0.0)"]
 
 [[package]]
 name = "httpx"
-version = "0.23.0"
+version = "0.24.1"
 description = "The next generation HTTP client."
 category = "main"
 optional = false
 python-versions = ">=3.7"
+files = [
+    {file = "httpx-0.24.1-py3-none-any.whl", hash = "sha256:06781eb9ac53cde990577af654bd990a4949de37a28bdb4a230d434f3a30b9bd"},
+    {file = "httpx-0.24.1.tar.gz", hash = "sha256:5853a43053df830c20f8110c5e69fe44d035d850b2dfe795e196f00fdb774bdd"},
+]
 
 [package.dependencies]
 certifi = "*"
-httpcore = ">=0.15.0,<0.16.0"
-rfc3986 = {version = ">=1.3,<2", extras = ["idna2008"]}
+httpcore = ">=0.15.0,<0.18.0"
+idna = "*"
 sniffio = "*"
 
 [package.extras]
 brotli = ["brotli", "brotlicffi"]
-cli = ["click (>=8.0.0,<9.0.0)", "pygments (>=2.0.0,<3.0.0)", "rich (>=10,<13)"]
+cli = ["click (>=8.0.0,<9.0.0)", "pygments (>=2.0.0,<3.0.0)", "rich (>=10,<14)"]
 http2 = ["h2 (>=3,<5)"]
 socks = ["socksio (>=1.0.0,<2.0.0)"]
 
@@ -133,6 +246,10 @@ description = "Internationalized Domain Names in Applications (IDNA)"
 category = "main"
 optional = false
 python-versions = ">=3.5"
+files = [
+    {file = "idna-3.4-py3-none-any.whl", hash = "sha256:90b77e79eaa3eba6de819a0c442c0b4ceefc341a7a2ab77d7562bf49f425c5c2"},
+    {file = "idna-3.4.tar.gz", hash = "sha256:814f528e8dead7d329833b91c5faa87d60bf71824cd12a7530b5526063d02cb4"},
+]
 
 [[package]]
 name = "imagesize"
@@ -141,30 +258,42 @@ description = "Getting image size from png/jpeg/jpeg2000/gif file"
 category = "main"
 optional = false
 python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*"
+files = [
+    {file = "imagesize-1.4.1-py2.py3-none-any.whl", hash = "sha256:0d8d18d08f840c19d0ee7ca1fd82490fdc3729b7ac93f49870406ddde8ef8d8b"},
+    {file = "imagesize-1.4.1.tar.gz", hash = "sha256:69150444affb9cb0d5cc5a92b3676f0b2fb7cd9ae39e947a5e11a36b4497cd4a"},
+]
 
 [[package]]
 name = "importlib-metadata"
-version = "5.0.0"
+version = "6.6.0"
 description = "Read metadata from Python packages"
 category = "main"
 optional = false
 python-versions = ">=3.7"
+files = [
+    {file = "importlib_metadata-6.6.0-py3-none-any.whl", hash = "sha256:43dd286a2cd8995d5eaef7fee2066340423b818ed3fd70adf0bad5f1fac53fed"},
+    {file = "importlib_metadata-6.6.0.tar.gz", hash = "sha256:92501cdf9cc66ebd3e612f1b4f0c0765dfa42f0fa38ffb319b6bd84dd675d705"},
+]
 
 [package.dependencies]
 zipp = ">=0.5"
 
 [package.extras]
-docs = ["furo", "jaraco.packaging (>=9)", "jaraco.tidelift (>=1.4)", "rst.linker (>=1.9)", "sphinx (>=3.5)"]
+docs = ["furo", "jaraco.packaging (>=9)", "jaraco.tidelift (>=1.4)", "rst.linker (>=1.9)", "sphinx (>=3.5)", "sphinx-lint"]
 perf = ["ipython"]
 testing = ["flake8 (<5)", "flufl.flake8", "importlib-resources (>=1.3)", "packaging", "pyfakefs", "pytest (>=6)", "pytest-black (>=0.3.7)", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-flake8", "pytest-mypy (>=0.9.1)", "pytest-perf (>=0.9.2)"]
 
 [[package]]
-name = "Jinja2"
+name = "jinja2"
 version = "3.1.2"
 description = "A very fast and expressive template engine."
 category = "main"
 optional = false
 python-versions = ">=3.7"
+files = [
+    {file = "Jinja2-3.1.2-py3-none-any.whl", hash = "sha256:6088930bfe239f0e6710546ab9c19c9ef35e29792895fed6e6e31a023a182a61"},
+    {file = "Jinja2-3.1.2.tar.gz", hash = "sha256:31351a702a408a9e7595a8fc6150fc3f43bb6bf7e319770cbc0db9df9437e852"},
+]
 
 [package.dependencies]
 MarkupSafe = ">=2.0"
@@ -173,97 +302,129 @@ MarkupSafe = ">=2.0"
 i18n = ["Babel (>=2.7)"]
 
 [[package]]
-name = "MarkupSafe"
-version = "2.1.1"
+name = "markupsafe"
+version = "2.1.2"
 description = "Safely add untrusted strings to HTML/XML markup."
 category = "main"
 optional = false
 python-versions = ">=3.7"
+files = [
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+]
 
 [[package]]
 name = "packaging"
-version = "21.3"
+version = "23.1"
 description = "Core utilities for Python packages"
 category = "main"
 optional = false
-python-versions = ">=3.6"
-
-[package.dependencies]
-pyparsing = ">=2.0.2,<3.0.5 || >3.0.5"
+python-versions = ">=3.7"
+files = [
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+]
 
 [[package]]
-name = "Pygments"
-version = "2.13.0"
+name = "pygments"
+version = "2.15.1"
 description = "Pygments is a syntax highlighting package written in Python."
 category = "main"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.7"
+files = [
+    {file = "Pygments-2.15.1-py3-none-any.whl", hash = "sha256:db2db3deb4b4179f399a09054b023b6a586b76499d36965813c71aa8ed7b5fd1"},
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+]
 
 [package.extras]
 plugins = ["importlib-metadata"]
 
 [[package]]
-name = "pyparsing"
-version = "3.0.9"
-description = "pyparsing module - Classes and methods to define and execute parsing grammars"
-category = "main"
-optional = false
-python-versions = ">=3.6.8"
-
-[package.extras]
-diagrams = ["jinja2", "railroad-diagrams"]
-
-[[package]]
-name = "pytz"
-version = "2022.4"
-description = "World timezone definitions, modern and historical"
-category = "main"
-optional = false
-python-versions = "*"
-
-[[package]]
 name = "requests"
-version = "2.28.1"
+version = "2.31.0"
 description = "Python HTTP for Humans."
 category = "main"
 optional = false
-python-versions = ">=3.7, <4"
+python-versions = ">=3.7"
+files = [
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+]
 
 [package.dependencies]
 certifi = ">=2017.4.17"
-charset-normalizer = ">=2,<3"
+charset-normalizer = ">=2,<4"
 idna = ">=2.5,<4"
-urllib3 = ">=1.21.1,<1.27"
+urllib3 = ">=1.21.1,<3"
 
 [package.extras]
 socks = ["PySocks (>=1.5.6,!=1.5.7)"]
-use_chardet_on_py3 = ["chardet (>=3.0.2,<6)"]
-
-[[package]]
-name = "rfc3986"
-version = "1.5.0"
-description = "Validating URI References per RFC 3986"
-category = "main"
-optional = false
-python-versions = "*"
-
-[package.dependencies]
-idna = {version = "*", optional = true, markers = "extra == \"idna2008\""}
-
-[package.extras]
-idna2008 = ["idna"]
+use-chardet-on-py3 = ["chardet (>=3.0.2,<6)"]
 
 [[package]]
 name = "setuptools"
-version = "65.4.1"
+version = "67.8.0"
 description = "Easily download, build, install, upgrade, and uninstall Python packages"
 category = "main"
 optional = false
 python-versions = ">=3.7"
+files = [
+    {file = "setuptools-67.8.0-py3-none-any.whl", hash = "sha256:5df61bf30bb10c6f756eb19e7c9f3b473051f48db77fddbe06ff2ca307df9a6f"},
+    {file = "setuptools-67.8.0.tar.gz", hash = "sha256:62642358adc77ffa87233bc4d2354c4b2682d214048f500964dbe760ccedf102"},
+]
 
 [package.extras]
-docs = ["furo", "jaraco.packaging (>=9)", "jaraco.tidelift (>=1.4)", "pygments-github-lexers (==0.0.5)", "rst.linker (>=1.9)", "sphinx (>=3.5)", "sphinx-favicon", "sphinx-hoverxref (<2)", "sphinx-inline-tabs", "sphinx-notfound-page (==0.8.3)", "sphinx-reredirects", "sphinxcontrib-towncrier"]
-testing = ["build[virtualenv]", "filelock (>=3.4.0)", "flake8 (<5)", "flake8-2020", "ini2toml[lite] (>=0.9)", "jaraco.envs (>=2.2)", "jaraco.path (>=3.2.0)", "mock", "pip (>=19.1)", "pip-run (>=8.8)", "pytest (>=6)", "pytest-black (>=0.3.7)", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-flake8", "pytest-mypy (>=0.9.1)", "pytest-perf", "pytest-xdist", "tomli-w (>=1.0.0)", "virtualenv (>=13.0.0)", "wheel"]
+docs = ["furo", "jaraco.packaging (>=9)", "jaraco.tidelift (>=1.4)", "pygments-github-lexers (==0.0.5)", "rst.linker (>=1.9)", "sphinx (>=3.5)", "sphinx-favicon", "sphinx-hoverxref (<2)", "sphinx-inline-tabs", "sphinx-lint", "sphinx-notfound-page (==0.8.3)", "sphinx-reredirects", "sphinxcontrib-towncrier"]
+testing = ["build[virtualenv]", "filelock (>=3.4.0)", "flake8-2020", "ini2toml[lite] (>=0.9)", "jaraco.envs (>=2.2)", "jaraco.path (>=3.2.0)", "pip (>=19.1)", "pip-run (>=8.8)", "pytest (>=6)", "pytest-black (>=0.3.7)", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-mypy (>=0.9.1)", "pytest-perf", "pytest-ruff", "pytest-timeout", "pytest-xdist", "tomli-w (>=1.0.0)", "virtualenv (>=13.0.0)", "wheel"]
 testing-integration = ["build[virtualenv]", "filelock (>=3.4.0)", "jaraco.envs (>=2.2)", "jaraco.path (>=3.2.0)", "pytest", "pytest-enabler", "pytest-xdist", "tomli", "virtualenv (>=13.0.0)", "wheel"]
 
 [[package]]
@@ -273,6 +434,10 @@ description = "Sniff out which async library your code is running under"
 category = "main"
 optional = false
 python-versions = ">=3.7"
+files = [
+    {file = "sniffio-1.3.0-py3-none-any.whl", hash = "sha256:eecefdce1e5bbfb7ad2eeaabf7c1eeb404d7757c379bd1f7e5cce9d8bf425384"},
+    {file = "sniffio-1.3.0.tar.gz", hash = "sha256:e60305c5e5d314f5389259b7f22aaa33d8f7dee49763119234af3755c55b9101"},
+]
 
 [[package]]
 name = "snowballstemmer"
@@ -281,26 +446,34 @@ description = "This package provides 29 stemmers for 28 languages generated from
 category = "main"
 optional = false
 python-versions = "*"
+files = [
+    {file = "snowballstemmer-2.2.0-py2.py3-none-any.whl", hash = "sha256:c8e1716e83cc398ae16824e5572ae04e0d9fc2c6b985fb0f900f5f0c96ecba1a"},
+    {file = "snowballstemmer-2.2.0.tar.gz", hash = "sha256:09b16deb8547d3412ad7b590689584cd0fe25ec8db3be37788be3810cbf19cb1"},
+]
 
 [[package]]
-name = "Sphinx"
-version = "5.2.3"
+name = "sphinx"
+version = "6.2.1"
 description = "Python documentation generator"
 category = "main"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.8"
+files = [
+    {file = "Sphinx-6.2.1.tar.gz", hash = "sha256:6d56a34697bb749ffa0152feafc4b19836c755d90a7c59b72bc7dfd371b9cc6b"},
+    {file = "sphinx-6.2.1-py3-none-any.whl", hash = "sha256:97787ff1fa3256a3eef9eda523a63dbf299f7b47e053cfcf684a1c2a8380c912"},
+]
 
 [package.dependencies]
 alabaster = ">=0.7,<0.8"
 babel = ">=2.9"
 colorama = {version = ">=0.4.5", markers = "sys_platform == \"win32\""}
-docutils = ">=0.14,<0.20"
+docutils = ">=0.18.1,<0.20"
 imagesize = ">=1.3"
 importlib-metadata = {version = ">=4.8", markers = "python_version < \"3.10\""}
 Jinja2 = ">=3.0"
 packaging = ">=21.0"
-Pygments = ">=2.12"
-requests = ">=2.5.0"
+Pygments = ">=2.13"
+requests = ">=2.25.0"
 snowballstemmer = ">=2.0"
 sphinxcontrib-applehelp = "*"
 sphinxcontrib-devhelp = "*"
@@ -311,16 +484,20 @@ sphinxcontrib-serializinghtml = ">=1.1.5"
 
 [package.extras]
 docs = ["sphinxcontrib-websupport"]
-lint = ["docutils-stubs", "flake8 (>=3.5.0)", "flake8-bugbear", "flake8-comprehensions", "flake8-simplify", "isort", "mypy (>=0.981)", "sphinx-lint", "types-requests", "types-typed-ast"]
-test = ["cython", "html5lib", "pytest (>=4.6)", "typed_ast"]
+lint = ["docutils-stubs", "flake8 (>=3.5.0)", "flake8-simplify", "isort", "mypy (>=0.990)", "ruff", "sphinx-lint", "types-requests"]
+test = ["cython", "filelock", "html5lib", "pytest (>=4.6)"]
 
 [[package]]
 name = "sphinx-intl"
-version = "2.0.1"
+version = "2.1.0"
 description = "Sphinx utility that make it easy to translate and to apply translation."
 category = "main"
 optional = false
-python-versions = ">=3.5"
+python-versions = ">=3.7"
+files = [
+    {file = "sphinx-intl-2.1.0.tar.gz", hash = "sha256:9d9849ae42515b39786824e99f1e30db0404c377b01bb022690fc932b0221c02"},
+    {file = "sphinx_intl-2.1.0-py3-none-any.whl", hash = "sha256:9798946b995989de691387651d70c3fc191275b587e2e519655541edfd7bbd68"},
+]
 
 [package.dependencies]
 babel = "*"
@@ -329,31 +506,39 @@ setuptools = "*"
 sphinx = "*"
 
 [package.extras]
-test = ["mock", "pytest"]
-transifex = ["transifex_client (>=0.11)"]
+test = ["mock", "pytest", "six"]
 
 [[package]]
 name = "sphinx-rtd-theme"
-version = "1.0.0"
+version = "1.2.0"
 description = "Read the Docs theme for Sphinx"
 category = "main"
 optional = false
-python-versions = ">=2.7,!=3.0.*,!=3.1.*,!=3.2.*,!=3.3.*"
+python-versions = "!=3.0.*,!=3.1.*,!=3.2.*,!=3.3.*,!=3.4.*,!=3.5.*,>=2.7"
+files = [
+    {file = "sphinx_rtd_theme-1.2.0-py2.py3-none-any.whl", hash = "sha256:f823f7e71890abe0ac6aaa6013361ea2696fc8d3e1fa798f463e82bdb77eeff2"},
+    {file = "sphinx_rtd_theme-1.2.0.tar.gz", hash = "sha256:a0d8bd1a2ed52e0b338cbe19c4b2eef3c5e7a048769753dac6a9f059c7b641b8"},
+]
 
 [package.dependencies]
-docutils = "<0.18"
-sphinx = ">=1.6"
+docutils = "<0.19"
+sphinx = ">=1.6,<7"
+sphinxcontrib-jquery = {version = ">=2.0.0,<3.0.0 || >3.0.0", markers = "python_version > \"3\""}
 
 [package.extras]
-dev = ["bump2version", "sphinxcontrib-httpdomain", "transifex-client"]
+dev = ["bump2version", "sphinxcontrib-httpdomain", "transifex-client", "wheel"]
 
 [[package]]
 name = "sphinxcontrib-applehelp"
-version = "1.0.2"
-description = "sphinxcontrib-applehelp is a sphinx extension which outputs Apple help books"
+version = "1.0.4"
+description = "sphinxcontrib-applehelp is a Sphinx extension which outputs Apple help books"
 category = "main"
 optional = false
-python-versions = ">=3.5"
+python-versions = ">=3.8"
+files = [
+    {file = "sphinxcontrib-applehelp-1.0.4.tar.gz", hash = "sha256:828f867945bbe39817c210a1abfd1bc4895c8b73fcaade56d45357a348a07d7e"},
+    {file = "sphinxcontrib_applehelp-1.0.4-py3-none-any.whl", hash = "sha256:29d341f67fb0f6f586b23ad80e072c8e6ad0b48417db2bde114a4c9746feb228"},
+]
 
 [package.extras]
 lint = ["docutils-stubs", "flake8", "mypy"]
@@ -366,6 +551,10 @@ description = "sphinxcontrib-devhelp is a sphinx extension which outputs Devhelp
 category = "main"
 optional = false
 python-versions = ">=3.5"
+files = [
+    {file = "sphinxcontrib-devhelp-1.0.2.tar.gz", hash = "sha256:ff7f1afa7b9642e7060379360a67e9c41e8f3121f2ce9164266f61b9f4b338e4"},
+    {file = "sphinxcontrib_devhelp-1.0.2-py2.py3-none-any.whl", hash = "sha256:8165223f9a335cc1af7ffe1ed31d2871f325254c0423bc0c4c7cd1c1e4734a2e"},
+]
 
 [package.extras]
 lint = ["docutils-stubs", "flake8", "mypy"]
@@ -373,23 +562,46 @@ test = ["pytest"]
 
 [[package]]
 name = "sphinxcontrib-htmlhelp"
-version = "2.0.0"
+version = "2.0.1"
 description = "sphinxcontrib-htmlhelp is a sphinx extension which renders HTML help files"
 category = "main"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.8"
+files = [
+    {file = "sphinxcontrib-htmlhelp-2.0.1.tar.gz", hash = "sha256:0cbdd302815330058422b98a113195c9249825d681e18f11e8b1f78a2f11efff"},
+    {file = "sphinxcontrib_htmlhelp-2.0.1-py3-none-any.whl", hash = "sha256:c38cb46dccf316c79de6e5515e1770414b797162b23cd3d06e67020e1d2a6903"},
+]
 
 [package.extras]
 lint = ["docutils-stubs", "flake8", "mypy"]
 test = ["html5lib", "pytest"]
 
 [[package]]
+name = "sphinxcontrib-jquery"
+version = "4.1"
+description = "Extension to include jQuery on newer Sphinx releases"
+category = "main"
+optional = false
+python-versions = ">=2.7"
+files = [
+    {file = "sphinxcontrib-jquery-4.1.tar.gz", hash = "sha256:1620739f04e36a2c779f1a131a2dfd49b2fd07351bf1968ced074365933abc7a"},
+    {file = "sphinxcontrib_jquery-4.1-py2.py3-none-any.whl", hash = "sha256:f936030d7d0147dd026a4f2b5a57343d233f1fc7b363f68b3d4f1cb0993878ae"},
+]
+
+[package.dependencies]
+Sphinx = ">=1.8"
+
+[[package]]
 name = "sphinxcontrib-jsmath"
 version = "1.0.1"
 description = "A sphinx extension which renders display math in HTML via JavaScript"
 category = "main"
 optional = false
 python-versions = ">=3.5"
+files = [
+    {file = "sphinxcontrib-jsmath-1.0.1.tar.gz", hash = "sha256:a9925e4a4587247ed2191a22df5f6970656cb8ca2bd6284309578f2153e0c4b8"},
+    {file = "sphinxcontrib_jsmath-1.0.1-py2.py3-none-any.whl", hash = "sha256:2ec2eaebfb78f3f2078e73666b1415417a116cc848b72e5172e596c871103178"},
+]
 
 [package.extras]
 test = ["flake8", "mypy", "pytest"]
@@ -401,6 +613,10 @@ description = "sphinxcontrib-qthelp is a sphinx extension which outputs QtHelp d
 category = "main"
 optional = false
 python-versions = ">=3.5"
+files = [
+    {file = "sphinxcontrib-qthelp-1.0.3.tar.gz", hash = "sha256:4c33767ee058b70dba89a6fc5c1892c0d57a54be67ddd3e7875a18d14cba5a72"},
+    {file = "sphinxcontrib_qthelp-1.0.3-py2.py3-none-any.whl", hash = "sha256:bd9fc24bcb748a8d51fd4ecaade681350aa63009a347a8c14e637895444dfab6"},
+]
 
 [package.extras]
 lint = ["docutils-stubs", "flake8", "mypy"]
@@ -413,6 +629,10 @@ description = "sphinxcontrib-serializinghtml is a sphinx extension which outputs
 category = "main"
 optional = false
 python-versions = ">=3.5"
+files = [
+    {file = "sphinxcontrib-serializinghtml-1.1.5.tar.gz", hash = "sha256:aa5f6de5dfdf809ef505c4895e51ef5c9eac17d0f287933eb49ec495280b6952"},
+    {file = "sphinxcontrib_serializinghtml-1.1.5-py2.py3-none-any.whl", hash = "sha256:352a9a00ae864471d3a7ead8d7d79f5fc0b57e8b3f95e9867eb9eb28999b92fd"},
+]
 
 [package.extras]
 lint = ["docutils-stubs", "flake8", "mypy"]
@@ -420,213 +640,39 @@ test = ["pytest"]
 
 [[package]]
 name = "urllib3"
-version = "1.26.12"
+version = "2.0.2"
 description = "HTTP library with thread-safe connection pooling, file post, and more."
 category = "main"
 optional = false
-python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*, !=3.5.*, <4"
+python-versions = ">=3.7"
+files = [
+    {file = "urllib3-2.0.2-py3-none-any.whl", hash = "sha256:d055c2f9d38dc53c808f6fdc8eab7360b6fdbbde02340ed25cfbcd817c62469e"},
+    {file = "urllib3-2.0.2.tar.gz", hash = "sha256:61717a1095d7e155cdb737ac7bb2f4324a858a1e2e6466f6d03ff630ca68d3cc"},
+]
 
 [package.extras]
-brotli = ["brotli (>=1.0.9)", "brotlicffi (>=0.8.0)", "brotlipy (>=0.6.0)"]
-secure = ["certifi", "cryptography (>=1.3.4)", "idna (>=2.0.0)", "ipaddress", "pyOpenSSL (>=0.14)", "urllib3-secure-extra"]
-socks = ["PySocks (>=1.5.6,!=1.5.7,<2.0)"]
+brotli = ["brotli (>=1.0.9)", "brotlicffi (>=0.8.0)"]
+secure = ["certifi", "cryptography (>=1.9)", "idna (>=2.0.0)", "pyopenssl (>=17.1.0)", "urllib3-secure-extra"]
+socks = ["pysocks (>=1.5.6,!=1.5.7,<2.0)"]
+zstd = ["zstandard (>=0.18.0)"]
 
 [[package]]
 name = "zipp"
-version = "3.8.1"
+version = "3.15.0"
 description = "Backport of pathlib-compatible object wrapper for zip files"
 category = "main"
 optional = false
 python-versions = ">=3.7"
+files = [
+    {file = "zipp-3.15.0-py3-none-any.whl", hash = "sha256:48904fc76a60e542af151aded95726c1a5c34ed43ab4134b597665c86d7ad556"},
+    {file = "zipp-3.15.0.tar.gz", hash = "sha256:112929ad649da941c23de50f356a2b5570c954b65150642bccdd66bf194d224b"},
+]
 
 [package.extras]
-docs = ["jaraco.packaging (>=9)", "jaraco.tidelift (>=1.4)", "rst.linker (>=1.9)", "sphinx"]
-testing = ["func-timeout", "jaraco.itertools", "pytest (>=6)", "pytest-black (>=0.3.7)", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-flake8", "pytest-mypy (>=0.9.1)"]
+docs = ["furo", "jaraco.packaging (>=9)", "jaraco.tidelift (>=1.4)", "rst.linker (>=1.9)", "sphinx (>=3.5)", "sphinx-lint"]
+testing = ["big-O", "flake8 (<5)", "jaraco.functools", "jaraco.itertools", "more-itertools", "pytest (>=6)", "pytest-black (>=0.3.7)", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-flake8", "pytest-mypy (>=0.9.1)"]
 
 [metadata]
-lock-version = "1.1"
+lock-version = "2.0"
 python-versions = "^3.9"
 content-hash = "b1f876a934295fce7c47e20a6e3e22f0d7d656f0b3b4a30e2eec50a3d643978e"
-
-[metadata.files]
-alabaster = [
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-certifi = [
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-    {file = "click-8.1.3.tar.gz", hash = "sha256:7682dc8afb30297001674575ea00d1814d808d6a36af415a82bd481d37ba7b8e"},
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-h11 = [
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-httpcore = [
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diff --git a/flatpak/org.onionshare.OnionShare.yaml b/flatpak/org.onionshare.OnionShare.yaml
index 9040d942..b455cb71 100644
--- a/flatpak/org.onionshare.OnionShare.yaml
+++ b/flatpak/org.onionshare.OnionShare.yaml
@@ -330,8 +330,8 @@ modules:
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-                sha256: 16fa4864408f655d35ec496218b85f79b3437c829e93320c7c9215ccfd92489e
+                url: https://files.pythonhosted.org/packages/38/60/300ad6f93adca578bf05d5f6cd1d854b7d140bebe2f9829561aa9977d9f3/typing_extensions-4.6.2-py3-none-any.whl
+                sha256: 3a8b36f13dd5fdc5d1b16fe317f5668545de77fa0b8e02006381fd49d731ab98
           - name: python3-werkzeug
             buildsystem: simple
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@@ -342,8 +342,8 @@ modules:
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-                url: https://files.pythonhosted.org/packages/c8/27/be6ddbcf60115305205de79c29004a0c6bc53cec814f733467b1bb89386d/Werkzeug-2.2.2-py3-none-any.whl
-                sha256: f979ab81f58d7318e064e99c4506445d60135ac5cd2e177a2de0089bfd4c9bd5
+                url: https://files.pythonhosted.org/packages/c2/2f/f0dc628295bd23571c962d5a349307d9c8796a05bfca6571659eaded38e2/Werkzeug-2.3.4-py3-none-any.whl
+                sha256: 48e5e61472fee0ddee27ebad085614ebedb7af41e88f687aaf881afb723a162f
       - name: onionshare-cli
         buildsystem: simple
         build-commands:
@@ -359,27 +359,31 @@ modules:
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-                urllib3 werkzeug zope-event zope-interface setuptools wheel Cython
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+                eventlet exceptiongroup flask flask-compress flask-socketio gevent gevent-websocket
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+                zope-interface Cython wheel
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               - type: file
+                url: https://files.pythonhosted.org/packages/30/bb/bf2944b8b88c65b797acc2c6a2cb0fb817f7364debf0675792e034013858/importlib_metadata-6.6.0-py3-none-any.whl
+                sha256: 43dd286a2cd8995d5eaef7fee2066340423b818ed3fd70adf0bad5f1fac53fed
+              - type: file
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-                sha256: 3d7f9739eb435d4b1338944abe23f49584bde5395f27487d2ee25ad9a8774a62
+                url: https://files.pythonhosted.org/packages/d6/0f/96b7309212a926c1448366e9ce69b081ea79d63265bde33f11cc9cfc2c07/psutil-5.9.5.tar.gz
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diff --git a/snap/snapcraft.yaml b/snap/snapcraft.yaml
index d7f798fb..cc3e8ed6 100644
--- a/snap/snapcraft.yaml
+++ b/snap/snapcraft.yaml
@@ -177,7 +177,9 @@ parts:
       colorama
       gevent-websocket
       stem==1.8.1
-      werkzeug==2.0.3
+      werkzeug==2.3.4
+      flask-compress
+      waitress
       # onionshare
       qrcode
       EOF