diff --git a/.ci/scripts/calc_constraints.py b/.ci/scripts/calc_constraints.py
index 993eb205120..29c8dd3f172 100755
--- a/.ci/scripts/calc_constraints.py
+++ b/.ci/scripts/calc_constraints.py
@@ -53,6 +53,9 @@ def to_upper_bound(req):
         if requirement.name == "pulpcore":
             # An exception to allow for pulpcore deprecation policy.
             return fetch_pulpcore_upper_bound(requirement)
+        # skip requirement with environment scopes. E.g 'foo==1.0.0;python_version>=3.9'
+        if requirement.marker:
+            return f"# ENVIRONMENT IS UNTRACKABLE: {req}"
         for spec in requirement.specifier:
             if spec.operator == "~=":
                 return f"# NO BETTER CONSTRAINT: {req}"
diff --git a/requirements.txt b/requirements.txt
index 98b076743e8..462dfbb4545 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -22,6 +22,8 @@ importlib-metadata>=6.0.1,<=6.0.1  # Pinned to fix opentelemetry dependency solv
 jinja2>=3.1,<=3.1.6
 json_stream>=2.3.2,<2.4
 jq>=1.6.0,<1.7.0
+# pycares is only a transitive dependency, but there is a combination of versions that expresses a bug.
+pycares<4.9;python_version<'3.12'  # pycares==4.9 + aiodns==3.2.0 + python<3.12 = trouble
 PyOpenSSL<25.0
 opentelemetry-distro[otlp]>=0.38b0,<=0.44b0
 opentelemetry-exporter-otlp-proto-http>=1.17.0,<=1.23.0