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diff --git a/tests/test_onionshare_web.py b/tests/test_onionshare_web.py
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+"""
+OnionShare | https://onionshare.org/
+
+Copyright (C) 2014-2018 Micah Lee <micah@micahflee.com>
+
+This program is free software: you can redistribute it and/or modify
+it under the terms of the GNU General Public License as published by
+the Free Software Foundation, either version 3 of the License, or
+(at your option) any later version.
+
+This program is distributed in the hope that it will be useful,
+but WITHOUT ANY WARRANTY; without even the implied warranty of
+MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+GNU General Public License for more details.
+
+You should have received a copy of the GNU General Public License
+along with this program.  If not, see <http://www.gnu.org/licenses/>.
+"""
+
+import contextlib
+import inspect
+import io
+import os
+import random
+import re
+import socket
+import sys
+import zipfile
+import tempfile
+
+import pytest
+
+from onionshare.common import Common
+from onionshare import strings
+from onionshare.web import Web
+from onionshare.settings import Settings
+
+DEFAULT_ZW_FILENAME_REGEX = re.compile(r'^onionshare_[a-z2-7]{6}.zip$')
+RANDOM_STR_REGEX = re.compile(r'^[a-z2-7]+$')
+
+
+def web_obj(common_obj, mode, num_files=0):
+    """ Creates a Web object, in either share mode or receive mode, ready for testing """
+    common_obj.load_settings()
+    strings.load_strings(common_obj)
+    web = Web(common_obj, False, mode)
+    web.generate_slug()
+    web.stay_open = True
+    web.running = True
+
+    web.app.testing = True
+
+    # Share mode
+    if mode == 'share':
+        # Add files
+        files = []
+        for i in range(num_files):
+            with tempfile.NamedTemporaryFile(delete=False) as tmp_file:
+                tmp_file.write(b'*' * 1024)
+                files.append(tmp_file.name)
+        web.share_mode.set_file_info(files)
+    # Receive mode
+    else:
+        pass
+
+    return web
+
+
+class TestWeb:
+    def test_share_mode(self, common_obj):
+        web = web_obj(common_obj, 'share', 3)
+        assert web.mode is 'share'
+        with web.app.test_client() as c:
+            # Load 404 pages
+            res = c.get('/')
+            res.get_data()
+            assert res.status_code == 404
+
+            res = c.get('/invalidslug'.format(web.slug))
+            res.get_data()
+            assert res.status_code == 404
+
+            # Load download page
+            res = c.get('/{}'.format(web.slug))
+            res.get_data()
+            assert res.status_code == 200
+
+            # Download
+            res = c.get('/{}/download'.format(web.slug))
+            res.get_data()
+            assert res.status_code == 200
+            assert res.mimetype == 'application/zip'
+
+    def test_share_mode_close_after_first_download_on(self, common_obj, temp_file_1024):
+        web = web_obj(common_obj, 'share', 3)
+        web.stay_open = False
+
+        assert web.running == True
+
+        with web.app.test_client() as c:
+            # Download the first time
+            res = c.get('/{}/download'.format(web.slug))
+            res.get_data()
+            assert res.status_code == 200
+            assert res.mimetype == 'application/zip'
+
+            assert web.running == False
+
+    def test_share_mode_close_after_first_download_off(self, common_obj, temp_file_1024):
+        web = web_obj(common_obj, 'share', 3)
+        web.stay_open = True
+
+        assert web.running == True
+
+        with web.app.test_client() as c:
+            # Download the first time
+            res = c.get('/{}/download'.format(web.slug))
+            res.get_data()
+            assert res.status_code == 200
+            assert res.mimetype == 'application/zip'
+            assert web.running == True
+
+    def test_receive_mode(self, common_obj):
+        web = web_obj(common_obj, 'receive')
+        assert web.mode is 'receive'
+
+        with web.app.test_client() as c:
+            # Load 404 pages
+            res = c.get('/')
+            res.get_data()
+            assert res.status_code == 404
+
+            res = c.get('/invalidslug'.format(web.slug))
+            res.get_data()
+            assert res.status_code == 404
+
+            # Load upload page
+            res = c.get('/{}'.format(web.slug))
+            res.get_data()
+            assert res.status_code == 200
+
+    def test_public_mode_on(self, common_obj):
+        web = web_obj(common_obj, 'receive')
+        common_obj.settings.set('public_mode', True)
+
+        with web.app.test_client() as c:
+            # Upload page should be accessible from /
+            res = c.get('/')
+            data1 = res.get_data()
+            assert res.status_code == 200
+
+            # /[slug] should be a 404
+            res = c.get('/{}'.format(web.slug))
+            data2 = res.get_data()
+            assert res.status_code == 404
+
+    def test_public_mode_off(self, common_obj):
+        web = web_obj(common_obj, 'receive')
+        common_obj.settings.set('public_mode', False)
+
+        with web.app.test_client() as c:
+            # / should be a 404
+            res = c.get('/')
+            data1 = res.get_data()
+            assert res.status_code == 404
+
+            # Upload page should be accessible from /[slug]
+            res = c.get('/{}'.format(web.slug))
+            data2 = res.get_data()
+            assert res.status_code == 200
+
+
+class TestZipWriterDefault:
+    @pytest.mark.parametrize('test_input', (
+        'onionshare_{}.zip'.format(''.join(
+            random.choice('abcdefghijklmnopqrstuvwxyz234567') for _ in range(6)
+        )) for _ in range(50)
+    ))
+    def test_default_zw_filename_regex(self, test_input):
+        assert bool(DEFAULT_ZW_FILENAME_REGEX.match(test_input))
+
+    def test_zw_filename(self, default_zw):
+        zw_filename = os.path.basename(default_zw.zip_filename)
+        assert bool(DEFAULT_ZW_FILENAME_REGEX.match(zw_filename))
+
+    def test_zipfile_filename_matches_zipwriter_filename(self, default_zw):
+        assert default_zw.z.filename == default_zw.zip_filename
+
+    def test_zipfile_allow_zip64(self, default_zw):
+        assert default_zw.z._allowZip64 is True
+
+    def test_zipfile_mode(self, default_zw):
+        assert default_zw.z.mode == 'w'
+
+    def test_callback(self, default_zw):
+        assert default_zw.processed_size_callback(None) is None
+
+    def test_add_file(self, default_zw, temp_file_1024_delete):
+        default_zw.add_file(temp_file_1024_delete)
+        zipfile_info = default_zw.z.getinfo(
+            os.path.basename(temp_file_1024_delete))
+
+        assert zipfile_info.compress_type == zipfile.ZIP_DEFLATED
+        assert zipfile_info.file_size == 1024
+
+    def test_add_directory(self, temp_dir_1024_delete, default_zw):
+        previous_size = default_zw._size  # size before adding directory
+        default_zw.add_dir(temp_dir_1024_delete)
+        assert default_zw._size == previous_size + 1024
+
+
+class TestZipWriterCustom:
+    @pytest.mark.parametrize('test_input', (
+        Common.random_string(
+            random.randint(2, 50),
+            random.choice((None, random.randint(2, 50)))
+        ) for _ in range(50)
+    ))
+    def test_random_string_regex(self, test_input):
+        assert bool(RANDOM_STR_REGEX.match(test_input))
+
+    def test_custom_filename(self, custom_zw):
+        assert bool(RANDOM_STR_REGEX.match(custom_zw.zip_filename))
+
+    def test_custom_callback(self, custom_zw):
+        assert custom_zw.processed_size_callback(None) == 'custom_callback'