diff --git a/canvasapi/requester.py b/canvasapi/requester.py
index f979866..e989962 100644
--- a/canvasapi/requester.py
+++ b/canvasapi/requester.py
@@ -68,8 +68,12 @@ class Requester(object):
         for i, kwarg in enumerate(_kwargs):
             kw, arg = kwarg
 
+            # Convert boolean objects to a lowercase string.
+            if isinstance(arg, bool):
+                _kwargs[i] = (kw, str(arg).lower())
+
             # Convert any datetime objects into ISO 8601 formatted strings.
-            if isinstance(arg, datetime):
+            elif isinstance(arg, datetime):
                 _kwargs[i] = (kw, arg.isoformat())
 
         # Determine the appropriate request method.

Automatically lowercase boolean strings before sending to Canvas
This will resolve any future weirdness like #64.
diff --git a/tests/test_requester.py b/tests/test_requester.py
index fb582a7..93e87a0 100644
--- a/tests/test_requester.py
+++ b/tests/test_requester.py
@@ -94,6 +94,24 @@ class TestRequester(unittest.TestCase):
         self.assertLessEqual(len(self.requester._cache), 5)
         self.assertEqual(response, self.requester._cache[0])
 
+    def test_request_lowercase_boolean(self, m):
+        def custom_matcher(request):
+            match_text = 'test=true&test2=false'
+            if request.text == match_text:
+                resp = requests.Response()
+                resp.status_code = 200
+                return resp
+
+        m.add_matcher(custom_matcher)
+
+        response = self.requester.request(
+            'POST',
+            'test',
+            test=True,
+            test2=False
+        )
+        self.assertEqual(response.status_code, 200)
+
     def test_request_400(self, m):
         register_uris({'requests': ['400']}, m)
 

pip install -e .[dev]
parse_log_pytest
requirements.txt
flake8 coverage pycodestyle pyflakes pytest
apt-get update apt-get install -y gcc
3.6
requirements.txt dev_requirements.txt
pytest --no-header -rA --tb=line --color=no -p no:cacheprovider -W ignore::DeprecationWarning
alabaster==0.7.13
attrs==22.2.0
Babel==2.11.0
-e git+https://github.com/ucfopen/canvasapi.git@fbe18169649f8e9dce1c85c5ef11dbc84641f935#egg=canvasapi
certifi==2021.5.30
charset-normalizer==2.0.12
coverage==6.2
docutils==0.17.1
flake8==5.0.4
idna==3.10
imagesize==1.4.1
importlib-metadata==4.2.0
iniconfig==1.1.1
Jinja2==3.0.3
MarkupSafe==2.0.1
mccabe==0.7.0
packaging==21.3
pluggy==1.0.0
py==1.11.0
pycodestyle==2.9.1
pyflakes==2.5.0
Pygments==2.14.0
pyparsing==3.1.4
pytest==7.0.1
pytz==2025.2
requests==2.27.1
requests-mock==1.12.1
six==1.17.0
snowballstemmer==2.2.0
Sphinx==4.3.2
sphinx-rtd-theme==1.3.0
sphinxcontrib-applehelp==1.0.2
sphinxcontrib-devhelp==1.0.2
sphinxcontrib-htmlhelp==2.0.0
sphinxcontrib-jquery==4.1
sphinxcontrib-jsmath==1.0.1
sphinxcontrib-qthelp==1.0.3
sphinxcontrib-serializinghtml==1.1.5
tomli==1.2.3
typing_extensions==4.1.1
urllib3==1.26.20
zipp==3.6.0

name: canvasapi
channels:
  - defaults
  - https://repo.anaconda.com/pkgs/main
  - https://repo.anaconda.com/pkgs/r
  - conda-forge
dependencies:
  - _libgcc_mutex=0.1=main
  - _openmp_mutex=5.1=1_gnu
  - ca-certificates=2025.2.25=h06a4308_0
  - certifi=2021.5.30=py36h06a4308_0
  - ld_impl_linux-64=2.40=h12ee557_0
  - libffi=3.3=he6710b0_2
  - libgcc-ng=11.2.0=h1234567_1
  - libgomp=11.2.0=h1234567_1
  - libstdcxx-ng=11.2.0=h1234567_1
  - ncurses=6.4=h6a678d5_0
  - openssl=1.1.1w=h7f8727e_0
  - pip=21.2.2=py36h06a4308_0
  - python=3.6.13=h12debd9_1
  - readline=8.2=h5eee18b_0
  - setuptools=58.0.4=py36h06a4308_0
  - sqlite=3.45.3=h5eee18b_0
  - tk=8.6.14=h39e8969_0
  - wheel=0.37.1=pyhd3eb1b0_0
  - xz=5.6.4=h5eee18b_1
  - zlib=1.2.13=h5eee18b_1
  - pip:
      - alabaster==0.7.13
      - attrs==22.2.0
      - babel==2.11.0
      - charset-normalizer==2.0.12
      - coverage==6.2
      - docutils==0.17.1
      - flake8==5.0.4
      - idna==3.10
      - imagesize==1.4.1
      - importlib-metadata==4.2.0
      - iniconfig==1.1.1
      - jinja2==3.0.3
      - markupsafe==2.0.1
      - mccabe==0.7.0
      - packaging==21.3
      - pluggy==1.0.0
      - py==1.11.0
      - pycodestyle==2.9.1
      - pyflakes==2.5.0
      - pygments==2.14.0
      - pyparsing==3.1.4
      - pytest==7.0.1
      - pytz==2025.2
      - requests==2.27.1
      - requests-mock==1.12.1
      - six==1.17.0
      - snowballstemmer==2.2.0
      - sphinx==4.3.2
      - sphinx-rtd-theme==1.3.0
      - sphinxcontrib-applehelp==1.0.2
      - sphinxcontrib-devhelp==1.0.2
      - sphinxcontrib-htmlhelp==2.0.0
      - sphinxcontrib-jquery==4.1
      - sphinxcontrib-jsmath==1.0.1
      - sphinxcontrib-qthelp==1.0.3
      - sphinxcontrib-serializinghtml==1.1.5
      - tomli==1.2.3
      - typing-extensions==4.1.1
      - urllib3==1.26.20
      - zipp==3.6.0
prefix: /opt/conda/envs/canvasapi

tests/test_requester.py::TestRequester::test_request_lowercase_boolean
tests/test_requester.py::TestRequester::test_request_400 tests/test_requester.py::TestRequester::test_request_401_InvalidAccessToken tests/test_requester.py::TestRequester::test_request_401_Unauthorized tests/test_requester.py::TestRequester::test_request_404 tests/test_requester.py::TestRequester::test_request_500 tests/test_requester.py::TestRequester::test_request_cache tests/test_requester.py::TestRequester::test_request_cache_clear_after_5 tests/test_requester.py::TestRequester::test_request_delete tests/test_requester.py::TestRequester::test_request_get tests/test_requester.py::TestRequester::test_request_get_datetime tests/test_requester.py::TestRequester::test_request_post tests/test_requester.py::TestRequester::test_request_post_datetime tests/test_requester.py::TestRequester::test_request_put
canvasapi/requester.py
canvasapi/requester.py