diff --git a/CHANGELOG.rst b/CHANGELOG.rst
index ee84610..8a601f0 100644
--- a/CHANGELOG.rst
+++ b/CHANGELOG.rst
@@ -14,6 +14,12 @@ Change Log
 Unreleased
 ~~~~~~~~~~
 
+[3.6.0] - 2024-07-24
+~~~~~~~~~~~~~~~~~~~~
+Added
+-----
+* New middleware ``edx_arch_experiments.datadog_diagnostics.middleware.DatadogDiagnosticMiddleware`` for logging diagnostics on traces in Datadog.
+
 [3.5.1] - 2024-07-15
 ~~~~~~~~~~~~~~~~~~~~
 Changed
diff --git a/edx_arch_experiments/__init__.py b/edx_arch_experiments/__init__.py
index 9828a05..ebdb6b8 100644
--- a/edx_arch_experiments/__init__.py
+++ b/edx_arch_experiments/__init__.py
@@ -2,4 +2,4 @@
 A plugin to include applications under development by the architecture team at 2U.
 """
 
-__version__ = '3.5.1'
+__version__ = '3.6.0'
diff --git a/edx_arch_experiments/datadog_diagnostics/middleware.py b/edx_arch_experiments/datadog_diagnostics/middleware.py
new file mode 100644
index 0000000..ae3ffed
--- /dev/null
+++ b/edx_arch_experiments/datadog_diagnostics/middleware.py
@@ -0,0 +1,75 @@
+"""
+Diagnostic middleware for Datadog.
+"""
+
+import logging
+
+from django.core.exceptions import MiddlewareNotUsed
+from edx_toggles.toggles import WaffleFlag
+
+log = logging.getLogger(__name__)
+
+# .. toggle_name: datadog.diagnostics.log_root_span
+# .. toggle_implementation: WaffleFlag
+# .. toggle_default: False
+# .. toggle_description: Enables logging of Datadog root span IDs for web requests.
+# .. toggle_warning: This is a noisy feature and so it should only be enabled
+#   for a percentage of requests.
+# .. toggle_use_cases: temporary
+# .. toggle_creation_date: 2024-07-24
+# .. toggle_target_removal_date: 2024-10-01
+# .. toggle_tickets: https://github.com/edx/edx-arch-experiments/issues/692
+LOG_ROOT_SPAN = WaffleFlag('datadog.diagnostics.log_root_span', module_name=__name__)
+
+
+# pylint: disable=missing-function-docstring
+class DatadogDiagnosticMiddleware:
+    """
+    Middleware to add diagnostic logging for Datadog.
+
+    Best added early in the middleware stack.
+
+    Only activates if ``ddtrace`` package is installed and
+    ``datadog.diagnostics.log_root_span`` Waffle flag is enabled.
+    """
+    def __init__(self, get_response):
+        self.get_response = get_response
+        self.error = False
+
+        try:
+            from ddtrace import tracer  # pylint: disable=import-outside-toplevel
+            self.dd_tracer = tracer
+        except ImportError:
+            # If import fails, don't even load this middleware.
+            raise MiddlewareNotUsed  # pylint: disable=raise-missing-from
+
+    def __call__(self, request):
+        return self.get_response(request)
+
+    def process_view(self, request, _view_func, _view_args, _view_kwargs):
+        try:
+            self.log_diagnostics(request)
+        except BaseException as e:
+            # If there's an error, it will probably hit every request,
+            # so let's just log it once.
+            if not self.error:
+                self.error = True
+                log.error(
+                    "Encountered error in DatadogDiagnosticMiddleware "
+                    f"(suppressing further errors): {e!r}"
+                )
+
+    def log_diagnostics(self, request):
+        """
+        Contains all the actual logging logic.
+        """
+        if LOG_ROOT_SPAN.is_enabled():
+            route_pattern = getattr(request.resolver_match, 'route', None)
+            local_root_span = self.dd_tracer.current_root_span()
+            current_span = self.dd_tracer.current_span()
+            # pylint: disable=protected-access
+            log.info(
+                f"Datadog span diagnostics: Route = {route_pattern}; "
+                f"local root span = {local_root_span._pprint()}; "
+                f"current span = {current_span._pprint()}"
+            )