diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 21069df..612e2e6 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -74,6 +74,21 @@ jobs:
       - name: Checkout
         uses: actions/checkout@v4
 
+      - name: Setup dev environment
+        run: |
+          pip install -r requirements-dev.txt
+          ### pytest-sentry configuration ###
+          if [ "$GITHUB_REPOSITORY" = "getsentry/self-hosted" ]; then
+            echo "PYTEST_SENTRY_DSN=${{ env.SELF_HOSTED_TESTING_DSN }}" >> $GITHUB_ENV
+            echo "PYTEST_SENTRY_TRACES_SAMPLE_RATE=0" >> $GITHUB_ENV
+
+            # This records failures on master to sentry in order to detect flakey tests, as it's
+            # expected that people have failing tests on their PRs
+            if [ "$GITHUB_REF" = "refs/heads/master" ]; then
+              echo "PYTEST_SENTRY_ALWAYS_REPORT=1" >> $GITHUB_ENV
+            fi
+          fi
+
       - name: Get Compose
         run: |
           # Always remove `docker compose` support as that's the newer version
diff --git a/_integration-test/custom-ca-roots/setup.sh b/_integration-test/custom-ca-roots/setup.sh
old mode 100644
new mode 100755
index 7cb6dd4..19be4fe
--- a/_integration-test/custom-ca-roots/setup.sh
+++ b/_integration-test/custom-ca-roots/setup.sh
@@ -1,3 +1,4 @@
+#!/usr/bin/env bash
 set -e
 export COMPOSE_FILE=docker-compose.yml:_integration-test/custom-ca-roots/docker-compose.test.yml
 
@@ -42,4 +43,4 @@ openssl req -x509 -newkey rsa:2048 -nodes -days 1 -keyout $TEST_NGINX_CONF_PATH/
 
 cp _integration-test/custom-ca-roots/test.py sentry/test-custom-ca-roots.py
 
-$dc up -d fixture-custom-ca-roots
+docker compose --ansi never up -d fixture-custom-ca-roots
diff --git a/_integration-test/custom-ca-roots/teardown.sh b/_integration-test/custom-ca-roots/teardown.sh
old mode 100644
new mode 100755
index 8b89299..35cee3c
--- a/_integration-test/custom-ca-roots/teardown.sh
+++ b/_integration-test/custom-ca-roots/teardown.sh
@@ -1,3 +1,4 @@
+#!/usr/bin/env bash
 $dc rm -s -f -v fixture-custom-ca-roots
 rm -f certificates/test-custom-ca-roots.crt sentry/test-custom-ca-roots.py
 unset COMPOSE_FILE
diff --git a/_integration-test/run.py b/_integration-test/run.py
new file mode 100644
index 0000000..885c115
--- /dev/null
+++ b/_integration-test/run.py
@@ -0,0 +1,209 @@
+import subprocess
+import os
+from functools import lru_cache
+from bs4 import BeautifulSoup
+import httpx
+import pytest
+import sentry_sdk
+import time
+import json
+import re
+from typing import Callable
+
+SENTRY_CONFIG_PY = "sentry/sentry.conf.py"
+SENTRY_TEST_HOST = os.getenv("SENTRY_TEST_HOST", "http://localhost:9000")
+TEST_USER = "test@example.com"
+TEST_PASS = "test123TEST"
+TIMEOUT_SECONDS = 60
+
+
+def poll_for_response(
+    request: str, client: httpx.Client, validator: Callable = None
+) -> httpx.Response:
+    for i in range(TIMEOUT_SECONDS):
+        response = client.get(
+            request, follow_redirects=True, headers={"Referer": SENTRY_TEST_HOST}
+        )
+        if response.status_code == 200:
+            if validator is None or validator(response.text):
+                break
+        time.sleep(1)
+    else:
+        raise AssertionError(
+            "timeout waiting for response status code 200 or valid data"
+        )
+    return response
+
+
+@lru_cache
+def get_sentry_dsn(client: httpx.Client) -> str:
+    response = poll_for_response(
+        f"{SENTRY_TEST_HOST}/api/0/projects/sentry/internal/keys/",
+        client,
+        lambda x: len(json.loads(x)[0]["dsn"]["public"]) > 0,
+    )
+    sentry_dsn = json.loads(response.text)[0]["dsn"]["public"]
+    return sentry_dsn
+
+
+@pytest.fixture(scope="session", autouse=True)
+def configure_self_hosted_environment():
+    subprocess.run(["docker", "compose", "--ansi", "never", "up", "-d"], check=True)
+    for i in range(TIMEOUT_SECONDS):
+        try:
+            response = httpx.get(SENTRY_TEST_HOST, follow_redirects=True)
+        except httpx.ConnectionError:
+            time.sleep(1)
+        else:
+            if response.status_code == 200:
+                break
+    else:
+        raise AssertionError("timeout waiting for self-hosted to come up")
+
+    # Create test user
+    subprocess.run(
+        [
+            "docker",
+            "compose",
+            "exec",
+            "web",
+            "sentry",
+            "createuser",
+            "--force-update",
+            "--superuser",
+            "--email",
+            TEST_USER,
+            "--password",
+            TEST_PASS,
+            "--no-input",
+        ],
+        check=True,
+        text=True,
+    )
+
+
+@pytest.fixture()
+def client_login():
+    client = httpx.Client()
+    response = client.get(SENTRY_TEST_HOST, follow_redirects=True)
+    parser = BeautifulSoup(response.text, "html.parser")
+    login_csrf_token = parser.find("input", {"name": "csrfmiddlewaretoken"})["value"]
+    login_response = client.post(
+        f"{SENTRY_TEST_HOST}/auth/login/sentry/",
+        follow_redirects=True,
+        data={
+            "op": "login",
+            "username": TEST_USER,
+            "password": TEST_PASS,
+            "csrfmiddlewaretoken": login_csrf_token,
+        },
+        headers={"Referer": f"{SENTRY_TEST_HOST}/auth/login/sentry/"},
+    )
+    assert login_response.status_code == 200
+    yield (client, login_response)
+
+
+def test_initial_redirect():
+    initial_auth_redirect = httpx.get(SENTRY_TEST_HOST, follow_redirects=True)
+    assert initial_auth_redirect.url == f"{SENTRY_TEST_HOST}/auth/login/sentry/"
+
+
+def test_login(client_login):
+    client, login_response = client_login
+    parser = BeautifulSoup(login_response.text, "html.parser")
+    script_tag = parser.find(
+        "script", string=lambda x: x and "window.__initialData" in x
+    )
+    assert script_tag is not None
+    json_data = json.loads(script_tag.text.split("=", 1)[1].strip().rstrip(";"))
+    assert json_data["isAuthenticated"] is True
+    assert json_data["user"]["username"] == "test@example.com"
+    assert json_data["user"]["isSuperuser"] is True
+    assert login_response.cookies["sc"] is not None
+    # Set up initial/required settings (InstallWizard request)
+    client.headers.update({"X-CSRFToken": login_response.cookies["sc"]})
+    response = client.put(
+        f"{SENTRY_TEST_HOST}/api/0/internal/options/?query=is:required",
+        follow_redirects=True,
+        headers={"Referer": SENTRY_TEST_HOST},
+        data={
+            "mail.use-tls": False,
+            "mail.username": "",
+            "mail.port": 25,
+            "system.admin-email": "test@example.com",
+            "mail.password": "",
+            "system.url-prefix": SENTRY_TEST_HOST,
+            "auth.allow-registration": False,
+            "beacon.anonymous": True,
+        },
+    )
+    assert response.status_code == 200
+
+
+def test_receive_event(client_login):
+    event_id = None
+    client, _ = client_login
+    with sentry_sdk.init(dsn=get_sentry_dsn(client)):
+        event_id = sentry_sdk.capture_exception(Exception("a failure"))
+    assert event_id is not None
+    response = poll_for_response(
+        f"{SENTRY_TEST_HOST}/api/0/projects/sentry/internal/events/{event_id}/", client
+    )
+    response_json = json.loads(response.text)
+    assert response_json["eventID"] == event_id
+    assert response_json["metadata"]["value"] == "a failure"
+
+
+def test_cleanup_crons_running():
+    docker_services = subprocess.check_output(
+        [
+            "docker",
+            "compose",
+            "--ansi",
+            "never",
+            "ps",
+            "-a",
+        ],
+        text=True,
+    )
+    pattern = re.compile(
+        r"(\-cleanup\s+running)|(\-cleanup[_-].+\s+Up\s+)", re.MULTILINE
+    )
+    cleanup_crons = pattern.findall(docker_services)
+    assert len(cleanup_crons) > 0
+
+
+def test_custom_cas():
+    try:
+        subprocess.run(["./_integration-test/custom-ca-roots/setup.sh"], check=True)
+        subprocess.run(
+            ["docker", "compose", "--ansi", "never", "run", "--no-deps", "web", "python3", "/etc/sentry/test-custom-ca-roots.py"], check=True
+        )
+    finally:
+        subprocess.run(["./_integration-test/custom-ca-roots/teardown.sh"], check=True)
+
+
+def test_receive_transaction_events(client_login):
+    client, _ = client_login
+    with sentry_sdk.init(
+        dsn=get_sentry_dsn(client), profiles_sample_rate=1.0, traces_sample_rate=1.0
+    ):
+
+        def placeholder_fn():
+            sum = 0
+            for i in range(5):
+                sum += i
+                time.sleep(0.25)
+
+        with sentry_sdk.start_transaction(op="task", name="Test Transactions"):
+            placeholder_fn()
+    poll_for_response(
+        f"{SENTRY_TEST_HOST}/api/0/organizations/sentry/events/?dataset=profiles&field=profile.id&project=1&statsPeriod=1h",
+        client,
+        lambda x: len(json.loads(x)["data"]) > 0,
+    )
+    poll_for_response(
+        f"{SENTRY_TEST_HOST}/api/0/organizations/sentry/events/?dataset=spansIndexed&field=id&project=1&statsPeriod=1h",
+        client,
+        lambda x: len(json.loads(x)["data"]) > 0,
+    )
diff --git a/integration-test.sh b/integration-test.sh
index 7006f80..29295ab 100755
--- a/integration-test.sh
+++ b/integration-test.sh
@@ -15,7 +15,7 @@ export MINIMIZE_DOWNTIME=0
 
 if [[ "$test_option" == "--initial-install" ]]; then
   echo "Testing initial install"
-  source _integration-test/run.sh
+  pytest --reruns 5 _integration-test/run.py
   source _integration-test/ensure-customizations-not-present.sh
   source _integration-test/ensure-backup-restore-works.sh
 elif [[ "$test_option" == "--customizations" ]]; then
@@ -34,7 +34,7 @@ EOT
   echo "Testing in-place upgrade and customizations"
   export MINIMIZE_DOWNTIME=1
   ./install.sh
-  source _integration-test/run.sh
+  pytest --reruns 5 _integration-test/run.py
   source _integration-test/ensure-customizations-work.sh
   source _integration-test/ensure-backup-restore-works.sh
 fi
diff --git a/requirements-dev.txt b/requirements-dev.txt
new file mode 100644
index 0000000..e87008c
--- /dev/null
+++ b/requirements-dev.txt
@@ -0,0 +1,6 @@
+sentry-sdk>=1.39.2
+pytest>=8.0.0
+pytest-rerunfailures>=11.0
+pytest-sentry>=0.1.11
+httpx>=0.25.2
+beautifulsoup4>=4.7.1