diff --git a/.gitignore b/.gitignore
index 882118e..fed8877 100644
--- a/.gitignore
+++ b/.gitignore
@@ -2,3 +2,11 @@
 env.yml
 # Taskfile binary via bootstrap.sh
 bin
+
+**/config.json
+
+# Python artifacts
+**pycache**
+**/*.pyc
+**/.venv/**
+**.egg-info**
diff --git a/services/healthcheck/.dockerignore b/services/healthcheck/.dockerignore
new file mode 100644
index 0000000..fc3df9e
--- /dev/null
+++ b/services/healthcheck/.dockerignore
@@ -0,0 +1 @@
+**/*_test.py
diff --git a/services/healthcheck/.python-version b/services/healthcheck/.python-version
new file mode 100644
index 0000000..e4fba21
--- /dev/null
+++ b/services/healthcheck/.python-version
@@ -0,0 +1 @@
+3.12
diff --git a/services/healthcheck/Dockerfile b/services/healthcheck/Dockerfile
new file mode 100644
index 0000000..294dd68
--- /dev/null
+++ b/services/healthcheck/Dockerfile
@@ -0,0 +1,15 @@
+FROM python:3.12 AS base
+
+WORKDIR /app
+
+COPY requirements.txt .
+
+RUN pip install -r requirements.txt
+
+FROM base AS app
+
+ENV HEALTHCHECK_CONFIG_PATH "/app/config.json"
+
+COPY healthcheck ./healthcheck
+
+CMD python -m uvicorn --host "0.0.0.0" healthcheck.main:app
diff --git a/services/healthcheck/README.md b/services/healthcheck/README.md
new file mode 100644
index 0000000..2ec9be8
--- /dev/null
+++ b/services/healthcheck/README.md
@@ -0,0 +1,21 @@
+# Healthcheck reporter
+
+Periodically checks if resources are reacheable and reports via a configurable webhook.
+
+## Configuration
+
+A `config.json` file should be provided and follow the schema outlined in `use_cases.Configuration`:
+
+```json
+{
+  "endpoints": {
+    "service-a": "https://service-a.com",
+    "service-b": "http://service-b:8080",
+    ...
+  },
+  "webhook_url": "https://my-webhook.com/",
+  "check_interval": 3600
+}
+```
+
+Every `check_interval` seconds, the application will attempt to reach each of the services and post a message summarizing the results to `webhook_url`.
diff --git a/services/healthcheck/build.sh b/services/healthcheck/build.sh
new file mode 100755
index 0000000..e5c5272
--- /dev/null
+++ b/services/healthcheck/build.sh
@@ -0,0 +1,5 @@
+#!/usr/bin/bash
+
+source ./constants.sh
+
+podman build . -t "$APP_IMAGE_NAME":"$IMAGE_VERSION"
diff --git a/services/healthcheck/constants.sh b/services/healthcheck/constants.sh
new file mode 100644
index 0000000..4c1a8ff
--- /dev/null
+++ b/services/healthcheck/constants.sh
@@ -0,0 +1,5 @@
+#!/bin/bash
+
+export APP_NAME="healthcheck"
+export APP_CONTAINER_NAME=$APP_NAME-app
+export APP_IMAGE_NAME=$CONTAINER_NAME_PREFIX-$APP_CONTAINER_NAME
diff --git a/services/healthcheck/healthcheck/__init__.py b/services/healthcheck/healthcheck/__init__.py
new file mode 100644
index 0000000..e69de29
diff --git a/services/healthcheck/healthcheck/conftest.py b/services/healthcheck/healthcheck/conftest.py
new file mode 100644
index 0000000..63d9ed6
--- /dev/null
+++ b/services/healthcheck/healthcheck/conftest.py
@@ -0,0 +1,42 @@
+"""
+Shared fixtures.
+"""
+
+import json
+
+import pytest
+
+
+@pytest.fixture
+def anyio_backend():
+    """Sets the default anyio backend."""
+    return "asyncio"
+
+
+@pytest.fixture(name="mock_configuration")
+def f_mock_configuration():
+    """Sample configuration"""
+    return {
+        "endpoints": {"test-service": "http://test.local"},
+        "webhook_url": "http://webhook.local",
+        "check_interval": 0.1,
+    }
+
+
+@pytest.fixture(name="set_up_mock_configuration")
+def f_set_up_mock_configuration(monkeypatch, tmp_path, mock_configuration):
+    """
+    Initializes a file with the sample configuration data and sets the
+    HEALTHCHECK_CONFIG_PATH variable to point to it.
+    """
+
+    def _fixture():
+        config_path = tmp_path / "config.json"
+
+        config_path.write_text(json.dumps(mock_configuration))
+
+        monkeypatch.setenv("HEALTHCHECK_CONFIG_PATH", str(config_path))
+
+        return config_path
+
+    return _fixture
diff --git a/services/healthcheck/healthcheck/main.py b/services/healthcheck/healthcheck/main.py
new file mode 100644
index 0000000..e82beef
--- /dev/null
+++ b/services/healthcheck/healthcheck/main.py
@@ -0,0 +1,55 @@
+"""
+Healthcheck reporting service.
+
+This periodically checks if certain URLs respond and
+reports on those responses.
+"""
+
+import asyncio
+import contextlib
+import logging
+
+import fastapi
+
+from healthcheck.tasks import report_on_statuses
+from healthcheck.use_cases import check_all_statuses, load_configuration
+
+logging.basicConfig(level=logging.INFO)
+
+logger = logging.getLogger(__name__)
+background_tasks = set()
+
+
+@contextlib.asynccontextmanager
+async def lifespan(_):
+    """Starts and stops asynchronous tasks on application lifecycle."""
+    status_checks = asyncio.create_task(report_on_statuses())
+    background_tasks.add(status_checks)
+    logger.info("Started reporting loop.")
+    yield
+
+    for task in background_tasks:
+        task.cancel()
+
+
+app = fastapi.FastAPI(lifespan=lifespan)
+
+
+@app.get("/")
+def alive():
+    """Is the application alive?"""
+    return 200
+
+
+@app.get("/config")
+def configuration():
+    """Check available configuration"""
+    return fastapi.responses.JSONResponse(load_configuration().model_dump())
+
+
+@app.get("/status")
+def check_status():
+    """Checks endpoints respond"""
+    config = load_configuration()
+
+    return check_all_statuses(config.endpoints)
diff --git a/services/healthcheck/healthcheck/main_test.py b/services/healthcheck/healthcheck/main_test.py
new file mode 100644
index 0000000..69cbdd6
--- /dev/null
+++ b/services/healthcheck/healthcheck/main_test.py
@@ -0,0 +1,52 @@
+"""
+Test coverage for endpoints and use cases.
+"""
+
+import pytest
+from fastapi.testclient import TestClient
+
+from healthcheck.main import app
+
+
+@pytest.fixture(name="client")
+def f_client():
+    """Test HTTP client."""
+    return TestClient(app)
+
+
+def test_alive_check_returns_200(client):
+    """Alive check returns 200."""
+    response = client.get("/")
+
+    assert response.status_code == 200
+
+
+def test_check_configuration_returns_config_and_200(
+    client, set_up_mock_configuration, mock_configuration
+):
+    """Check configuration returns the loaded configuration."""
+    set_up_mock_configuration()
+
+    response = client.get("/config")
+
+    assert response.json() == mock_configuration
+
+
+def test_check_status_returns_status_summary(
+    httpx_mock, client, set_up_mock_configuration
+):
+    """
+    Check status endpoint checks all configured endpoints and reports on
+    availability.
+    """
+    set_up_mock_configuration()
+
+    httpx_mock.add_response(url="http://test.local", status_code=200)
+
+    response = client.get("/status")
+
+    assert response.status_code == 200
+
+    response_body = response.json()
+
+    assert response_body == {"test-service": True}
diff --git a/services/healthcheck/healthcheck/tasks.py b/services/healthcheck/healthcheck/tasks.py
new file mode 100644
index 0000000..9f8f2bd
--- /dev/null
+++ b/services/healthcheck/healthcheck/tasks.py
@@ -0,0 +1,41 @@
+"""
+Defines asynchronous tasks loaded on startup.
+"""
+
+import logging
+import time
+import typing
+
+from healthcheck.use_cases import check_all_statuses, load_configuration, post_message
+
+logger = logging.getLogger(__name__)
+
+
+async def report_on_statuses(*, max_iterations: typing.Optional[int] = None):
+    """
+    Reports on all registered services.
+    """
+
+    config = load_configuration()
+
+    iterations = 0
+
+    while max_iterations is None or iterations < max_iterations:
+        statuses = check_all_statuses(config.endpoints)
+
+        message_lines = []
+
+        for service, status in statuses.items():
+            if status:
+                message_lines.append(f"✅ {service} is healthy.")
+            else:
+                message_lines.append(f"🔥 {service} is not responding normally.")
+
+        message = "\n".join(message_lines)
+
+        logger.info(message)
+
+        post_message(config.webhook_url, message)
+        iterations += 1
+
+        time.sleep(config.check_interval)
diff --git a/services/healthcheck/healthcheck/tasks_test.py b/services/healthcheck/healthcheck/tasks_test.py
new file mode 100644
index 0000000..5076245
--- /dev/null
+++ b/services/healthcheck/healthcheck/tasks_test.py
@@ -0,0 +1,113 @@
+"""
+Asynchronous task tests.
+"""
+
+import json
+
+import pytest
+
+from healthcheck.tasks import report_on_statuses
+
+pytestmark = pytest.mark.anyio
+
+
+async def test_report_on_statuses_pings_registered_endpoints(
+    httpx_mock, mock_configuration, set_up_mock_configuration
+):
+    """Each run pings each specified service."""
+    mock_url = mock_configuration["endpoints"]["test-service"]
+
+    set_up_mock_configuration()
+
+    httpx_mock.add_response(url=mock_url)
+    httpx_mock.add_response(url=mock_configuration["webhook_url"])
+
+    await report_on_statuses(max_iterations=1)
+
+    requests_captured = httpx_mock.get_requests()
+
+    get_requests = tuple(
+        request for request in requests_captured if request.method == "GET"
+    )
+
+    assert len(get_requests) == 1
+    assert str(get_requests[0].url) == mock_url
+
+
+async def test_report_on_statuses_posts_message_to_the_webhook_url(
+    httpx_mock, mock_configuration, set_up_mock_configuration
+):
+    """Each run posts a message to the webhook for reporting."""
+    mock_url = mock_configuration["endpoints"]["test-service"]
+
+    set_up_mock_configuration()
+
+    httpx_mock.add_response(url=mock_url)
+    httpx_mock.add_response(url=mock_configuration["webhook_url"])
+
+    await report_on_statuses(max_iterations=1)
+
+    requests_captured = httpx_mock.get_requests()
+
+    post_requests = tuple(
+        request for request in requests_captured if request.method == "POST"
+    )
+
+    # Only one webhook request is made.
+    assert len(post_requests) == 1
+
+    webhook_post = post_requests[0]
+
+    # The request goes to the webhook URL.
+    assert str(webhook_post.url) == mock_configuration["webhook_url"]
+
+
+@pytest.mark.parametrize(
+    "status_code, expected",
+    [[200, "is healthy"], [400, "is not responding normally"]],
+    ids=["healthy", "unhealthy"],
+)
+async def test_report_on_statuses_posts_message_describing_service_status(
+    status_code, expected, httpx_mock, mock_configuration, set_up_mock_configuration
+):
+    """Each message describes whether the service is healthy or not."""
+    mock_url = mock_configuration["endpoints"]["test-service"]
+
+    set_up_mock_configuration()
+
+    httpx_mock.add_response(url=mock_url, status_code=status_code)
+    httpx_mock.add_response(url=mock_configuration["webhook_url"])
+
+    await report_on_statuses(max_iterations=1)
+
+    requests_captured = httpx_mock.get_requests()
+
+    post_requests = tuple(
+        request for request in requests_captured if request.method == "POST"
+    )
+
+    webhook_post = post_requests[0]
+
+    posted_message = json.loads(webhook_post.content)
+
+    assert expected in posted_message["content"]
+
+
+@pytest.mark.parametrize("iterations", [1, 10])
+async def test_report_on_statuses_runs_at_most_n_times_if_max_iterations_specified(
+    iterations, httpx_mock, mock_configuration, set_up_mock_configuration
+):
+    """Iterations can be capped to a certain count."""
+    mock_url = mock_configuration["endpoints"]["test-service"]
+
+    set_up_mock_configuration()
+
+    httpx_mock.add_response(url=mock_url)
+    httpx_mock.add_response(url=mock_configuration["webhook_url"])
+
+    await report_on_statuses(max_iterations=iterations)
+
+    requests_captured = httpx_mock.get_requests()
+
+    # Each iteration pings once, posts once.
+    assert len(requests_captured) == 2 * iterations
diff --git a/services/healthcheck/healthcheck/use_cases.py b/services/healthcheck/healthcheck/use_cases.py
new file mode 100644
index 0000000..f5eaef6
--- /dev/null
+++ b/services/healthcheck/healthcheck/use_cases.py
@@ -0,0 +1,97 @@
+"""
+Business logic for endpoints and tasks.
+"""
+
+import functools
+import json
+import logging
+import os
+import pathlib
+
+import httpx
+import pydantic
+
+logger = logging.getLogger(__name__)
+
+
+class Configuration(pydantic.BaseModel):
+    """Service configuration"""
+
+    endpoints: dict[str, str]
+    webhook_url: str
+    check_interval: float
+
+
+@functools.cache
+def load_configuration() -> Configuration:
+    """
+    Loads configuration from disk.
+
+    If the HEALTHCHECK_CONFIG_PATH env variable is not set, raises.
+    If the configuration file is not valid json, raises.
+    If the configuration data doesn't satisfy the Configuration type, raises.
+    """
+    raw_config_path = os.getenv("HEALTHCHECK_CONFIG_PATH")
+
+    if not raw_config_path:
+        raise RuntimeError(
+            "No configuration path provided. HEALTHCHECK_CONFIG_PATH must be set."
+        )
+
+    config_path = pathlib.Path(raw_config_path)
+
+    if not config_path.exists():
+        raise RuntimeError(f"Configuration file does not exist at {config_path}")
+
+    with open(config_path, "r", encoding="utf8") as config_file:
+        config_raw = config_file.read()
+
+    try:
+        config = json.loads(config_raw)
+    except Exception as e:
+        raise RuntimeError(
+            "Failed to parse configuration file at {config_path}:  {str(e)}"
+        ) from e
+
+    return Configuration(**config)
+
+
+def check_all_statuses(endpoints: dict[str, str]) -> dict[str, bool]:
+    """
+    Pings all the specified endpoint and produces a mapping describing
+    whether the target responded with a "OK-ish" status (i.e. 2XX).
+
+    Exceptions raised while requesting are logged and reported as failures
+    to check.
+    """
+
+    status_summary = {}
+
+    for service_name, service_url in endpoints.items():
+        try:
+            response = httpx.get(service_url)
+            response.raise_for_status()
+        except Exception:  # pylint: disable=broad-except
+            logger.exception(
+                "Failed to check health of %s: (%s)", service_name, service_url
+            )
+            status_summary[service_name] = False
+        else:
+            status_summary[service_name] = True
+
+    return status_summary
+
+
+def post_message(webhook_url: str, message: str):
+    """
+    Posts a message to a Discord webhook URL.
+
+    See https://discord.com/developers/docs/resources/webhook#execute-webhook for
+    payload schema.
+    """
+
+    payload = {"content": message}
+
+    response = httpx.post(webhook_url, json=payload)
+
+    response.raise_for_status()
diff --git a/services/healthcheck/healthcheck/use_cases_test.py b/services/healthcheck/healthcheck/use_cases_test.py
new file mode 100644
index 0000000..3bff39d
--- /dev/null
+++ b/services/healthcheck/healthcheck/use_cases_test.py
@@ -0,0 +1,14 @@
+"""
+Business logic tests.
+"""
+
+from healthcheck.use_cases import load_configuration
+
+
+def test_load_configuration(set_up_mock_configuration, mock_configuration):
+    """Checks that configuration can be loaded."""
+    set_up_mock_configuration()
+
+    configuration = load_configuration()
+
+    assert configuration.model_dump() == mock_configuration
diff --git a/services/healthcheck/pyproject.toml b/services/healthcheck/pyproject.toml
new file mode 100644
index 0000000..5a8db28
--- /dev/null
+++ b/services/healthcheck/pyproject.toml
@@ -0,0 +1,34 @@
+[project]
+name = "healthcheck"
+version = "0.0.0"
+requires-python = ">= 3.12"
+dependencies = [
+    "fastapi",
+    "httpx",
+    "pydantic",
+    "uvicorn[standard]",
+]
+
+[project.optional-dependencies]
+dev = [
+    "anyio",
+    "black",
+    "pylint",
+    "httpx",
+    "pytest",
+    "pytest-httpx",
+    "isort",
+]
+
+[tool.setuptools]
+packages = ["healthcheck"]
+
+[tool.pytest.ini_options]
+pythonpath=[
+    ".",
+    "./healthcheck",
+]
+python_files=[
+    "*_test.py"
+]
+
diff --git a/services/healthcheck/requirements.txt b/services/healthcheck/requirements.txt
new file mode 100644
index 0000000..f6ab74d
--- /dev/null
+++ b/services/healthcheck/requirements.txt
@@ -0,0 +1,58 @@
+annotated-types==0.6.0
+    # via pydantic
+anyio==4.3.0
+    # via
+    #   httpx
+    #   starlette
+    #   watchfiles
+certifi==2024.2.2
+    # via
+    #   httpcore
+    #   httpx
+click==8.1.7
+    # via uvicorn
+fastapi==0.110.0
+    # via healthcheck (pyproject.toml)
+h11==0.14.0
+    # via
+    #   httpcore
+    #   uvicorn
+httpcore==1.0.4
+    # via httpx
+httptools==0.6.1
+    # via uvicorn
+httpx==0.27.0
+    # via healthcheck (pyproject.toml)
+idna==3.6
+    # via
+    #   anyio
+    #   httpx
+pydantic==2.6.3
+    # via
+    #   fastapi
+    #   healthcheck (pyproject.toml)
+pydantic-core==2.16.3
+    # via pydantic
+python-dotenv==1.0.1
+    # via uvicorn
+pyyaml==6.0.1
+    # via uvicorn
+sniffio==1.3.1
+    # via
+    #   anyio
+    #   httpx
+starlette==0.36.3
+    # via fastapi
+typing-extensions==4.10.0
+    # via
+    #   fastapi
+    #   pydantic
+    #   pydantic-core
+uvicorn[standard]==0.27.1
+    # via healthcheck (pyproject.toml)
+uvloop==0.19.0
+    # via uvicorn
+watchfiles==0.21.0
+    # via uvicorn
+websockets==12.0
+    # via uvicorn
diff --git a/services/healthcheck/requirements_dev.txt b/services/healthcheck/requirements_dev.txt
new file mode 100644
index 0000000..fe4a2be
--- /dev/null
+++ b/services/healthcheck/requirements_dev.txt
@@ -0,0 +1,134 @@
+annotated-types==0.6.0
+    # via
+    #   -c requirements.txt
+    #   pydantic
+anyio==4.3.0
+    # via
+    #   -c requirements.txt
+    #   healthcheck (pyproject.toml)
+    #   httpx
+    #   starlette
+    #   watchfiles
+astroid==3.1.0
+    # via pylint
+black==24.2.0
+    # via healthcheck (pyproject.toml)
+certifi==2024.2.2
+    # via
+    #   -c requirements.txt
+    #   httpcore
+    #   httpx
+click==8.1.7
+    # via
+    #   -c requirements.txt
+    #   black
+    #   uvicorn
+dill==0.3.8
+    # via pylint
+fastapi==0.110.0
+    # via
+    #   -c requirements.txt
+    #   healthcheck (pyproject.toml)
+h11==0.14.0
+    # via
+    #   -c requirements.txt
+    #   httpcore
+    #   uvicorn
+httpcore==1.0.4
+    # via
+    #   -c requirements.txt
+    #   httpx
+httptools==0.6.1
+    # via
+    #   -c requirements.txt
+    #   uvicorn
+httpx==0.27.0
+    # via
+    #   -c requirements.txt
+    #   healthcheck (pyproject.toml)
+    #   pytest-httpx
+idna==3.6
+    # via
+    #   -c requirements.txt
+    #   anyio
+    #   httpx
+iniconfig==2.0.0
+    # via pytest
+isort==5.13.2
+    # via
+    #   healthcheck (pyproject.toml)
+    #   pylint
+mccabe==0.7.0
+    # via pylint
+mypy-extensions==1.0.0
+    # via black
+packaging==23.2
+    # via
+    #   black
+    #   pytest
+pathspec==0.12.1
+    # via black
+platformdirs==4.2.0
+    # via
+    #   black
+    #   pylint
+pluggy==1.4.0
+    # via pytest
+pydantic==2.6.3
+    # via
+    #   -c requirements.txt
+    #   fastapi
+    #   healthcheck (pyproject.toml)
+pydantic-core==2.16.3
+    # via
+    #   -c requirements.txt
+    #   pydantic
+pylint==3.1.0
+    # via healthcheck (pyproject.toml)
+pytest==8.0.2
+    # via
+    #   healthcheck (pyproject.toml)
+    #   pytest-httpx
+pytest-httpx==0.30.0
+    # via healthcheck (pyproject.toml)
+python-dotenv==1.0.1
+    # via
+    #   -c requirements.txt
+    #   uvicorn
+pyyaml==6.0.1
+    # via
+    #   -c requirements.txt
+    #   uvicorn
+sniffio==1.3.1
+    # via
+    #   -c requirements.txt
+    #   anyio
+    #   httpx
+starlette==0.36.3
+    # via
+    #   -c requirements.txt
+    #   fastapi
+tomlkit==0.12.4
+    # via pylint
+typing-extensions==4.10.0
+    # via
+    #   -c requirements.txt
+    #   fastapi
+    #   pydantic
+    #   pydantic-core
+uvicorn[standard]==0.27.1
+    # via
+    #   -c requirements.txt
+    #   healthcheck (pyproject.toml)
+uvloop==0.19.0
+    # via
+    #   -c requirements.txt
+    #   uvicorn
+watchfiles==0.21.0
+    # via
+    #   -c requirements.txt
+    #   uvicorn
+websockets==12.0
+    # via
+    #   -c requirements.txt
+    #   uvicorn
diff --git a/services/healthcheck/script/bootstrap.sh b/services/healthcheck/script/bootstrap.sh
new file mode 100755
index 0000000..8066e30
--- /dev/null
+++ b/services/healthcheck/script/bootstrap.sh
@@ -0,0 +1,9 @@
+#!/usr/bin/bash
+
+python -m venv .venv
+
+. .venv/bin/activate
+
+pip install -U pip~=24.0 pip-tools~=7.3.0
+
+pip-sync requirements.txt requirements_dev.txt
diff --git a/services/healthcheck/script/lock-deps.sh b/services/healthcheck/script/lock-deps.sh
new file mode 100755
index 0000000..3c22c01
--- /dev/null
+++ b/services/healthcheck/script/lock-deps.sh
@@ -0,0 +1,6 @@
+#!/usr/bin/bash
+
+PYTHON=.venv/bin/python
+
+$PYTHON -m piptools compile -o requirements.txt pyproject.toml --no-header \
+    && $PYTHON -m piptools compile -o requirements_dev.txt --no-header --extra dev --constraint requirements.txt pyproject.toml 
diff --git a/services/healthcheck/start.sh b/services/healthcheck/start.sh
new file mode 100755
index 0000000..4b8a6be
--- /dev/null
+++ b/services/healthcheck/start.sh
@@ -0,0 +1,10 @@
+#!/usr/bin/bash
+
+source ./constants.sh
+
+podman run \
+    --detach \
+    --pod services \
+    -v ./config.json:/app/config.json \
+    --name "$APP_NAME" \
+    "$APP_IMAGE_NAME":"$IMAGE_VERSION"
diff --git a/services/healthcheck/stop.sh b/services/healthcheck/stop.sh
new file mode 100644
index 0000000..818f1cd
--- /dev/null
+++ b/services/healthcheck/stop.sh
@@ -0,0 +1,5 @@
+#!/usr/bin/bash
+
+source ./constants.sh
+
+podman rm -f $APP_NAME