diff --git a/.azure-pipelines/azure-pipelines.yml b/.azure-pipelines/azure-pipelines.yml
index 6daa3020..b7b15b4d 100644
--- a/.azure-pipelines/azure-pipelines.yml
+++ b/.azure-pipelines/azure-pipelines.yml
@@ -251,7 +251,7 @@ stages:
           testFormat: devel/rhel/{0}
           targets:
             - test: '7.9'
-            - test: '8.5'
+            - test: '8.5/pypi-latest'
           groups:
             - 1
             - 2
diff --git a/tests/integration/targets/docker_config/tasks/test_docker_config.yml b/tests/integration/targets/docker_config/tasks/test_docker_config.yml
index da900bbc..4b77b538 100644
--- a/tests/integration/targets/docker_config/tasks/test_docker_config.yml
+++ b/tests/integration/targets/docker_config/tasks/test_docker_config.yml
@@ -21,10 +21,10 @@
     ignore_errors: yes
     register: output
 
-  - name: assert failure when called with no name
+  - name: Assert failure when called with no name
     assert:
       that:
-         - 'output.failed'
+         - 'output is failed'
          - 'output.msg == "missing required arguments: name"'
 
   - name: Test parameters
@@ -34,10 +34,10 @@
     ignore_errors: yes
     register: output
 
-  - name: assert failure when called with no data
+  - name: Assert failure when called with no data
     assert:
       that:
-         - 'output.failed'
+         - 'output is failed'
          - 'output.msg == "state is present but any of the following are missing: data, data_src"'
 
   - name: Create config
@@ -56,9 +56,10 @@
     register: inspect
     ignore_errors: yes
 
-  - debug: var=inspect
+  - debug:
+      var: inspect
 
-  - name: assert config creation succeeded
+  - name: Assert config creation succeeded
     assert:
       that:
          - "'db_password' in inspect.stdout"
@@ -76,10 +77,10 @@
       state: present
     register: output
 
-  - name: assert create config is idempotent
+  - name: Assert create config is idempotent
     assert:
       that:
-         - not output.changed
+         - output is not changed
 
   - name: Write config into file
     copy:
@@ -94,10 +95,10 @@
       state: present
     register: output
 
-  - name: assert create config is idempotent
+  - name: Assert create config is idempotent
     assert:
       that:
-         - not output.changed
+         - output is not changed
 
   - name: Create config again (base64)
     docker_config:
@@ -107,10 +108,10 @@
       state: present
     register: output
 
-  - name: assert create config (base64) is idempotent
+  - name: Assert create config (base64) is idempotent
     assert:
       that:
-         - not output.changed
+         - output is not changed
 
   - name: Update config
     docker_config:
@@ -119,10 +120,10 @@
       state: present
     register: output
 
-  - name: assert config was updated
+  - name: Assert config was updated
     assert:
       that:
-         - output.changed
+         - output is changed
          - output.config_id != config_id
 
   - name: Remove config
@@ -135,10 +136,10 @@
     register: output
     ignore_errors: yes
 
-  - name: assert config was removed
+  - name: Assert config was removed
     assert:
       that:
-        - output.failed
+        - output is failed
 
   - name: Remove config
     docker_config:
@@ -146,10 +147,10 @@
       state: absent
     register: output
 
-  - name: assert remove config is idempotent
+  - name: Assert remove config is idempotent
     assert:
       that:
-        - not output.changed
+        - output is not changed
 
 # Rolling update
 
@@ -170,9 +171,10 @@
     register: inspect
     ignore_errors: yes
 
-  - debug: var=inspect
+  - debug:
+      var: inspect
 
-  - name: assert config creation succeeded
+  - name: Assert config creation succeeded
     assert:
       that:
          - "'rolling_password' in inspect.stdout"
@@ -193,10 +195,10 @@
       state: present
     register: new_output
 
-  - name: assert that new version is created
+  - name: Assert that new version is created
     assert:
       that:
-         - new_output.changed
+         - new_output is changed
          - new_output.config_id != original_output.config_id
          - new_output.config_name != original_output.config_name
          - new_output.config_name == 'rolling_password_v2'
@@ -212,20 +214,20 @@
     register: output
     ignore_errors: yes
 
-  - name: assert config was removed
+  - name: Assert config was removed
     assert:
       that:
-        - output.failed
+        - output is failed
 
   - name: Check that config is removed
     command: "docker config inspect {{ new_output.config_id }}"
     register: output
     ignore_errors: yes
 
-  - name: assert config was removed
+  - name: Assert config was removed
     assert:
       that:
-        - output.failed
+        - output is failed
 
 # template_driver tests
 
@@ -263,7 +265,7 @@
     - name: Assert failure when called with invalid template_driver
       assert:
         that:
-           - 'output.failed'
+           - 'output is failed'
            - 'output.msg == "value of template_driver must be one of: golang, got: not a template driver"'
 
     - name: Create config again
@@ -296,12 +298,13 @@
       debug:
         var: inspect
 
-    - name: assert config creation succeeded
+    - name: Assert config creation succeeded
       assert:
         that:
            - "'db_password' in inspect.stdout"
            - "'ansible_key' in inspect.stdout"
-           - "'\"Data\": \"default\"' in inspect.stdout"
+           # According to the API docs, 'Data' is "Base64-url-safe-encoded (RFC 4648) config data."
+           - "'\"Data\": \"e3sgLlNlcnZpY2UuTmFtZSB9fQ==\"' in inspect.stdout"
            - "'Templating' in inspect.stdout"
            - "'\"Name\": \"golang\"' in inspect.stdout"
 
@@ -318,7 +321,7 @@
     - name: Assert config was removed
       assert:
         that:
-          - output.failed
+          - output is failed
 
   always:
   - name: Remove a Swarm cluster
diff --git a/tests/integration/targets/setup_docker/tasks/main.yml b/tests/integration/targets/setup_docker/tasks/main.yml
index 35c52655..b4eaa4d7 100644
--- a/tests/integration/targets/setup_docker/tasks/main.yml
+++ b/tests/integration/targets/setup_docker/tasks/main.yml
@@ -50,11 +50,11 @@
         docker_pip_package_limit: '<4.3.0'
       when: (docker_api_version_stdout.stdout | default('0.0')) is version('1.39', '<')
 
-    - name: Install Python requirements
+    - name: Install/upgrade Python requirements
       pip:
-        state: present
         name: "{{ [docker_pip_package ~ docker_pip_package_limit] + docker_pip_extra_packages }}"
         extra_args: "-c {{ remote_constraints }}"
+        state: "{{ 'latest' if force_docker_sdk_for_python_pypi | default(false) else 'present' }}"
       notify: cleanup docker
 
     # Detect docker CLI, API and docker-py versions
diff --git a/tests/utils/shippable/remote.sh b/tests/utils/shippable/remote.sh
index 76065b81..55b4aa48 100755
--- a/tests/utils/shippable/remote.sh
+++ b/tests/utils/shippable/remote.sh
@@ -7,20 +7,33 @@ IFS='/:' read -ra args <<< "$1"
 
 platform="${args[0]}"
 version="${args[1]}"
+target="shippable/posix/"
 
-if [ "${#args[@]}" -gt 2 ]; then
+force_python=""
+
+if [ "${#args[@]}" -gt 3 ]; then
+    if [ "${args[2]}" == "pypi-latest" ]; then
+        echo 'force_docker_sdk_for_python_pypi: true' >> tests/integration/interation_config.yml
+        if [ "${platform}" == "rhel" ] && [[ "${version}" =~ ^8\. ]]; then
+            # Use Python 3.8 on RHEL 8.x - TODO: this might be no longer necessary for high enough minor version! Check!
+            force_python="--python 3.8"
+        fi
+    else
+        echo "Invalid Docker SDK for Python version: '${args[2]}'"
+        exit 254
+    fi
+    target="shippable/posix/group${args[3]}/"
+elif [ "${#args[@]}" -gt 2 ]; then
     target="shippable/posix/group${args[2]}/"
-else
-    target="shippable/posix/"
 fi
 
 stage="${S:-prod}"
 provider="${P:-default}"
 
-if [ "${platform}" == "rhel" ] && [[ "${version}" =~ ^8 ]]; then
+if [ "${platform}" == "rhel" ] && [[ "${version}" =~ ^8\. ]]; then
     echo "pynacl >= 1.4.0, < 1.5.0; python_version == '3.6'" >> tests/utils/constraints.txt
 fi
 
 # shellcheck disable=SC2086
 ansible-test integration --color -v --retry-on-error "${target}" ${COVERAGE:+"$COVERAGE"} ${CHANGED:+"$CHANGED"} ${UNSTABLE:+"$UNSTABLE"} \
-    --remote "${platform}/${version}" --remote-terminate always --remote-stage "${stage}" --remote-provider "${provider}"
+    --remote "${platform}/${version}" --remote-terminate always --remote-stage "${stage}" --remote-provider "${provider}" ${force_python}