diff --git a/images/Containerfile.core.base b/images/Containerfile.core.base
index 2363943d..16d90315 100644
--- a/images/Containerfile.core.base
+++ b/images/Containerfile.core.base
@@ -74,22 +74,6 @@ RUN dnf -y install python${PYTHON_VERSION} python3-cryptography python${PYTHON_V
     getcap /usr/bin/newuidmap  | grep cap_setuid || dnf -y reinstall -y shadow-utils && \
     dnf clean all
 
-# Needed to prevent the wrong version of cryptography from being installed,
-# which would break PyOpenSSL.
-# Need to install optional dep, rhsm, for pulp-certguard
-RUN pip3 install --upgrade pip setuptools wheel && \
-    rm -rf /root/.cache/pip && \
-    pip3 install  \
-         rhsm \
-         setproctitle \
-         gunicorn \
-         python-nginx \
-         django-auth-ldap \
-         django-storages\[boto3,azure]\>=1.12.2 \
-         requests\[use_chardet_on_py3] && \
-         rm -rf /root/.cache/pip
-
-
 RUN groupadd -g 700 --system pulp
 RUN useradd -d /var/lib/pulp --system -u 700 -g pulp pulp
 
diff --git a/images/pulp-minimal/nightly/Containerfile.core b/images/pulp-minimal/nightly/Containerfile.core
index 69cb582b..da03d443 100644
--- a/images/pulp-minimal/nightly/Containerfile.core
+++ b/images/pulp-minimal/nightly/Containerfile.core
@@ -12,7 +12,9 @@ RUN pip3 install git+https://github.com/pulp/pulpcore.git#egg=pulpcore \
   git+https://github.com/pulp/pulp_npm.git \
   git+https://github.com/pulp/pulp_ostree.git \
   git+https://github.com/pulp/pulp_python.git \
-  git+https://github.com/pulp/pulp_rpm.git
+  git+https://github.com/pulp/pulp_rpm.git \
+  rhsm && \
+  rm -rf /root/.cache/pip
 
 USER pulp:pulp
 RUN PULP_STATIC_ROOT=/var/lib/operator/static/ PULP_CONTENT_ORIGIN=localhost \
diff --git a/images/pulp-minimal/stable/Containerfile.core b/images/pulp-minimal/stable/Containerfile.core
index 8adf72d7..84b57f20 100644
--- a/images/pulp-minimal/stable/Containerfile.core
+++ b/images/pulp-minimal/stable/Containerfile.core
@@ -22,7 +22,8 @@ RUN pip3 install --upgrade \
   pulp-maven${PULP_MAVEN_VERSION} \
   pulp-python${PULP_PYTHON_VERSION} \
   pulp-rpm${PULP_RPM_VERSION} \
-  pulp-ostree${PULP_OSTREE_VERSION} && \
+  pulp-ostree${PULP_OSTREE_VERSION} \
+  rhsm && \
   rm -rf /root/.cache/pip
 
 # Prevent pip-installed /usr/local/bin/pulp-content from getting run instead of
diff --git a/images/pulp/nightly/Containerfile b/images/pulp/nightly/Containerfile
index deb36a3c..fba26df3 100644
--- a/images/pulp/nightly/Containerfile
+++ b/images/pulp/nightly/Containerfile
@@ -14,7 +14,7 @@ RUN pip3 install --upgrade \
   git+https://github.com/pulp/pulp_ostree@main \
   git+https://github.com/pulp/pulp_python@main \
   git+https://github.com/pulp/pulp_rpm@main \
-  requests && \
+  rhsm && \
   rm -rf /root/.cache/pip
 
 USER pulp:pulp
diff --git a/images/pulp/stable/Containerfile b/images/pulp/stable/Containerfile
index 874e03a7..778dd191 100644
--- a/images/pulp/stable/Containerfile
+++ b/images/pulp/stable/Containerfile
@@ -25,6 +25,7 @@ RUN pip3 install --upgrade \
   pulp-python${PULP_PYTHON_VERSION} \
   pulp-rpm${PULP_RPM_VERSION} \
   pulp-ostree${PULP_OSTREE_VERSION} \
+  rhsm \
   requests && \
   rm -rf /root/.cache/pip