diff --git a/.github/workflows/build_test.yml b/.github/workflows/build_test.yml
index 6ba704ab..e4eb40c1 100644
--- a/.github/workflows/build_test.yml
+++ b/.github/workflows/build_test.yml
@@ -1,4 +1,4 @@
-name: "BuildAndTest"
+name: "Build And Test"
 
 on:
   push:
@@ -8,16 +8,16 @@ on:
 
 jobs:
   build:
-    name: Build and test driver
+    name: Build and Test Driver
     runs-on: ubuntu-20.04
     strategy:
       matrix:
-        python-version: [3.6]
+        python-version: [3.6, 3.7, 3.12]
 
     steps:
-    - uses: actions/checkout@v2
+    - uses: actions/checkout@v4
     - name: Set up Python ${{ matrix.python-version }}
-      uses: actions/setup-python@v2
+      uses: actions/setup-python@v5
       with:
         python-version: ${{ matrix.python-version }}
     - name: Install dependencies
@@ -32,9 +32,6 @@ jobs:
         # exit-zero treats all errors as warnings. The GitHub editor is 127 chars wide
         flake8 . --count --exit-zero --max-complexity=10 --max-line-length=127 --statistics
     - name: Run Tests
-      run: py.test -v --cov=swimlane --cov-report=xml
-    - name: Run Codacy Coverage
-      env:
-        CODACY_PROJECT_TOKEN: ${{ secrets.CODACY_PROJECT_TOKEN }}
-      run: python-codacy-coverage -r coverage.xml
+      run: |
+        python -m pytest
 
diff --git a/.github/workflows/codeql-analysis.yml b/.github/workflows/codeql-analysis.yml
index 209ef1c9..2aafd983 100644
--- a/.github/workflows/codeql-analysis.yml
+++ b/.github/workflows/codeql-analysis.yml
@@ -1,4 +1,4 @@
-name: "CodeQL"
+name: "CodeQL Analysis"
 
 on:
   push:
diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index be218891..58f9d776 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -1,7 +1,7 @@
 # This workflow is responsible for publishing  packages to PyPi
 # and creating offline packages
 
-name: "Release new version"
+name: "Release New Version"
 
 on:
   - workflow_call
@@ -12,12 +12,12 @@ jobs:
     name: Publish to PyPi
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v2
+      - uses: actions/checkout@v4
 
       - name: Setup python
-        uses: actions/setup-python@v2
+        uses: actions/setup-python@v5
         with:
-          python-version: 3.7
+          python-version: 3.12
 
       - name: Update PIP tools
         run: |
diff --git a/.gitignore b/.gitignore
index fbc86700..2b05feb3 100644
--- a/.gitignore
+++ b/.gitignore
@@ -81,4 +81,6 @@ functional_tests/pydriver-report.html
 
 # virtual environment
 venv3/
-venv/
\ No newline at end of file
+venv/
+
+test-script.py
\ No newline at end of file
diff --git a/Makefile b/Makefile
index 6ef49ca5..44d660b2 100644
--- a/Makefile
+++ b/Makefile
@@ -11,7 +11,7 @@ docs:
 	cd docs/ && make html
 
 release:
-	python setup.py sdist bdist_wheel upload -r swimlane
+	python3 setup.py sdist bdist_wheel upload -r swimlane
 
 build-offline-installer:
-	python2.7 offline_installer/build_installer.py
+	python3 offline_installer/build_installer.py
diff --git a/README.rst b/README.rst
index e9a3ad26..973a89ad 100644
--- a/README.rst
+++ b/README.rst
@@ -63,27 +63,28 @@ Install the required PIP packages with the command
 ## Executing
 
 The test suite allows for overriding the target server and user parameters via the following arguments:
-
---url default="https://localhost"
---user default="admin"
---pass This is the password for the user defined above.
---skipverify This is for allowing the version of PyDriver to not match the version of Swimlane.
+ ::
+    pytest 
+    --url default="https://localhost"
+    --user default="admin"
+    --pass This is the password for the user defined above.
+    --skipverify This is for allowing the version of PyDriver to not match the version of Swimlane.
 
 To run a specific test and skip the version verification:
 
-pytest driver_tests/test_app_adaptor.py --skipverify
+::
+    pytest driver_tests/test_app_adaptor.py --skipverify
 
 To run all the tests against 10.20.30.40:
-
-pytest --url "https://10.20.30.40"
-
+ ::
+    pytest --url "https://10.20.30.40"
 
 .. NOTE::
     All of the data created for testing purposes is cleaned up.
 
     No preset data is needed beyond the base user.
 
-    These tests are Python 2 and 3 compatible.
+    These tests are Python 3.6+ compatible.
 
 Issues
 ------
diff --git a/docs/examples/client.rst b/docs/examples/client.rst
index 3c7820a5..64d4c468 100644
--- a/docs/examples/client.rst
+++ b/docs/examples/client.rst
@@ -97,6 +97,46 @@ additional requests made by using the client automatically.
 
 The `verify_ssl` parameter is ignored when connecting over HTTP.
 
+Retry Requests
+^^^^^^^^^^^^^
+
+Initial client connection and all failed requests are retried upon recieving :class:`HTTP 5XX` errors (server errors) if the :class:`retry` parameter is enabled.
+The default retry options are set as following:
+    - retry = True
+    - max_retries = 5
+    - retry_interval = 5 (in seconds)
+
+To override the default retry options used by all library methods, provide them during client instantiation.
+
+.. code-block:: python
+
+    from swimlane import Swimlane
+
+    swimlane = Swimlane(
+        '192.168.1.1',
+        'username',
+        'password',
+        retry=True,
+        max_retries=3,
+        retry_interval=10 # in seconds
+    )
+The :meth:`swimlane.Swimlane.request` method can also accept the optional retry options that will override the
+global defaults for the single request.
+
+.. code-block:: python
+
+    from swimlane import Swimlane
+
+    swimlane = Swimlane('192.168.1.1', 'username', 'password')
+
+    response = swimlane.request(
+        'post',
+        'some/endpoint',
+        ...,
+        retry=True,
+        max_retries=3,
+        retry_interval=10 # in seconds
+    )
 
 Resource Caching
 ^^^^^^^^^^^^^^^^
@@ -200,7 +240,7 @@ All provided keyword arguments will be passed to the underlying :meth:`requests.
 
 .. note::
 
-    Any 400/500 responses will raise :class:`requests.HTTPError` automatically.
+    Any 400/500 responses will raise :class:`requests.HTTPError` automatically after Max Retry attempts are exceeded.
 
 
 Request Timeouts
@@ -270,9 +310,6 @@ disabled by setting `verify_server_version=False`.
         'password',
         verify_server_version=False
     )
-
-
-
 Available Adapters
 ------------------
 
diff --git a/docs/index.rst b/docs/index.rst
index 4a599ec2..af107d63 100644
--- a/docs/index.rst
+++ b/docs/index.rst
@@ -50,10 +50,6 @@ Install/upgrade to latest release::
 
     pip install -U swimlane
 
-Install/upgrade to latest release for platform v2.x::
-
-    pip install -U "swimlane>=2,<3"
-
 
 Offline Installer
 ^^^^^^^^^^^^^^^^^
diff --git a/functional_tests/requirements.txt b/functional_tests/requirements.txt
index 04de3b14..0af0bfb7 100644
--- a/functional_tests/requirements.txt
+++ b/functional_tests/requirements.txt
@@ -1,3 +1,3 @@
 Faker==0.8.15
 pytest>=3.5.0
-pytest-html>=1.22.1
+pytest-html>=1.22.1
\ No newline at end of file
diff --git a/pytest.ini b/pytest.ini
new file mode 100644
index 00000000..5ee64771
--- /dev/null
+++ b/pytest.ini
@@ -0,0 +1,2 @@
+[pytest]
+testpaths = tests
diff --git a/requirements.txt b/requirements.txt
index 16124f20..19f28794 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -1,6 +1,7 @@
-cachetools>=2.0,<2.1
+cachetools>=4.2.4
 certifi>=2017
-pendulum==2.1.2
+pendulum==2.1.2; python_version<='3.7'
+pendulum==3.0.0; python_version>='3.8'
 pyjwt>=2.4.0
 pyuri>=0.3,<0.4
 requests[security]>=2,<3
diff --git a/setup.cfg b/setup.cfg
index 3debf7ee..06f8414f 100644
--- a/setup.cfg
+++ b/setup.cfg
@@ -6,7 +6,3 @@ test=pytest
 
 [wheel]
 universal=1
-
-[tool:pytest]
-python_paths = .
-testpaths = tests
diff --git a/setup.py b/setup.py
index 0df8916c..d9f06fbd 100644
--- a/setup.py
+++ b/setup.py
@@ -11,11 +11,12 @@ def parse_requirements(requirement_file):
 
 
 setup(
-    version="10.14.0",
+    version="10.18.0",
     name="swimlane",
     author="Swimlane",
     author_email="info@swimlane.com",
     url="https://github.com/swimlane/swimlane-python",
+    python_requires=">=3.6",
     packages=find_packages(exclude=('tests', 'tests.*')),
     description="Python driver for the Swimlane API",
     long_description=long_description,
@@ -29,9 +30,12 @@ def parse_requirements(requirement_file):
         "License :: OSI Approved :: GNU Affero General Public License v3",
         "Development Status :: 5 - Production/Stable",
         "Programming Language :: Python",
-        "Programming Language :: Python :: 3.4",
-        "Programming Language :: Python :: 3.5",
         "Programming Language :: Python :: 3.6",
-        "Programming Language :: Python :: 3.7"
+        "Programming Language :: Python :: 3.7",
+        "Programming Language :: Python :: 3.8",
+        "Programming Language :: Python :: 3.9",
+        "Programming Language :: Python :: 3.10",
+        "Programming Language :: Python :: 3.11",
+        "Programming Language :: Python :: 3.12"
     ]
 )
diff --git a/swimlane/core/client.py b/swimlane/core/client.py
index d3e2238c..13df8885 100644
--- a/swimlane/core/client.py
+++ b/swimlane/core/client.py
@@ -5,10 +5,12 @@
 import jwt
 import pendulum
 import requests
+import time
 from pyuri import URI
 from requests.compat import json
 from requests.packages import urllib3
 from requests.structures import CaseInsensitiveDict
+from requests.exceptions import ConnectionError
 from six.moves.urllib.parse import urljoin
 
 from swimlane.core.adapters import GroupAdapter, UserAdapter, AppAdapter, HelperAdapter
@@ -46,6 +48,9 @@ class Swimlane(object):
             caching. Disabled by default
         access_token (str): Authentication token, used in lieu of a username and password
         write_to_read_only (bool): Enable the ability to write to Read-only fields
+        retry (bool): Retry request when error code is >= 500
+        max_retries (int): Maximum number of retry attempts
+        retry_interval (int): Time interval (in seconds) between two retry attempts
 
     Attributes:
         host (pyuri.URI): Full RFC-1738 URL pointing to Swimlane host
@@ -92,7 +97,10 @@ def __init__(
             verify_server_version=True,
             resource_cache_size=0,
             access_token=None,
-            write_to_read_only=False
+            write_to_read_only: bool=False,
+            retry: bool=True,
+            max_retries: int=5,
+            retry_interval: int=5
     ):
         self.__verify_auth_params(username, password, access_token)
 
@@ -111,6 +119,10 @@ def __init__(
 
         self._session = WrappedSession()
         self._session.verify = verify_ssl
+        
+        self.retry = retry
+        self.max_retries = max_retries
+        self.retry_interval = retry_interval
 
         if username is not None and password is not None:
             self._session.auth = SwimlaneJwtAuth(
@@ -215,17 +227,41 @@ def request(self, method, api_endpoint, **kwargs):
             kwargs['headers'] = headers
 
             kwargs['data'] = json.dumps(json_data, sort_keys=True, separators=(',', ':'))
-
-        response = self._session.request(method, urljoin(str(self.host) + self._api_root, api_endpoint), **kwargs)
-
-        # Roll 400 errors up into SwimlaneHTTP400Errors with specific Swimlane error code support
-        try:
-            response.raise_for_status()
-        except requests.HTTPError as error:
-            if error.response.status_code == 400:
-                raise SwimlaneHTTP400Error(error)
-            else:
-                raise error
+        
+        # Retry logic
+        req_retry = kwargs.pop('retry', self.retry)
+        
+        req_max_retries = kwargs.pop('max_retries', self.max_retries)
+        if not isinstance(req_max_retries, int):
+            raise TypeError('max_retries should be an integer')
+        if req_max_retries <= 0:
+            raise ValueError('max_retries should be a positive integer')
+        
+        req_retry_interval = kwargs.pop('retry_interval', self.retry_interval)
+        if not isinstance(req_retry_interval, int):
+            raise TypeError('retry_interval should be an integer')
+        if req_retry_interval <= 0:
+            raise ValueError('retry_interval should be a positive integer')
+        
+        while not req_max_retries<0:
+            response = self._session.request(method, urljoin(str(self.host) + self._api_root, api_endpoint), **kwargs)
+
+            # Roll 400 errors up into SwimlaneHTTP400Errors with specific Swimlane error code support
+            try:
+                response.raise_for_status()
+                # Exit loop on successful request
+                req_max_retries = -1 
+            except requests.HTTPError as error:
+                if error.response.status_code == 400:
+                    raise SwimlaneHTTP400Error(error)
+                else:
+                    if req_retry and req_max_retries>0 and error.response.status_code>=500:
+                        req_max_retries -= 1
+                        time.sleep(req_retry_interval)
+                        continue
+                    elif req_max_retries == 0:
+                        raise ConnectionError(f'Max retries exceeded. Caused by ({error})')
+                    raise error
 
         return response
 
diff --git a/swimlane/core/resources/usergroup.py b/swimlane/core/resources/usergroup.py
index 4d19dcbe..c4984049 100644
--- a/swimlane/core/resources/usergroup.py
+++ b/swimlane/core/resources/usergroup.py
@@ -158,6 +158,9 @@ def _evaluate(self):
                 yield element
         else:
             for user_id in self.__user_ids:
-                element = self._swimlane.users.get(id=user_id)
-                self._elements.append(element)
-                yield element
+                try:
+                    element = self._swimlane.users.get(id=user_id)
+                    self._elements.append(element)
+                    yield element
+                except StopIteration:
+                    return
diff --git a/test-requirements.txt b/test-requirements.txt
index d05620e1..cdf6caac 100644
--- a/test-requirements.txt
+++ b/test-requirements.txt
@@ -1,7 +1,6 @@
-coverage
+faker
 mock
-pytest==3.10.1
-pytest-cov==2.8.1
+pytest>=6.2.5
 pytest-pythonpath
 tox
 pytz
diff --git a/tox.ini b/tox.ini
index 633d2a96..dacf525b 100644
--- a/tox.ini
+++ b/tox.ini
@@ -1,5 +1,5 @@
 [tox]
-envlist = py27,py34,py35,py36
+envlist = py36,py37,py38,py39,py310,py311,py312
 
 [testenv]
 passenv = LANG