diff --git a/tests/integration/targets/generic_ssh_connection/tasks/main.yml b/tests/integration/targets/generic_ssh_connection/tasks/main.yml
index 61ddc040..470fc9ef 100644
--- a/tests/integration/targets/generic_ssh_connection/tasks/main.yml
+++ b/tests/integration/targets/generic_ssh_connection/tasks/main.yml
@@ -54,7 +54,7 @@
       - 'output.volumes is not defined'
       - 'output.images is not defined'
       - 'output.disk_usage is not defined'
-  when: output is succeeded or 'Install paramiko package to enable' in output.msg
+  when: output is succeeded or 'Install paramiko package to enable' not in output.msg
   # For whatever reason, even though paramiko is installed, *sometimes* this error
   # shows up. I have no idea why it sometimes works and sometimes not...
 
@@ -75,7 +75,11 @@
       - 'output.volumes is not defined'
       - 'output.images is not defined'
       - 'output.disk_usage is not defined'
-  when: docker_py_version is version('4.4.0', '>=')
+  when: docker_py_version is version('4.4.0', '>=') and (output is succeeded or 'Install paramiko package to enable' not in output.msg)
+  # For whatever reason, even though paramiko is installed, *sometimes* this error
+  # shows up. I have no idea why it sometimes works and sometimes not...
+  # (Also note that due to the way Docker SDK for Python has been written, SSH by
+  # shell only works if paramiko is around...)
 
 - name: Make sure we got information
   assert:
diff --git a/tests/utils/constraints.txt b/tests/utils/constraints.txt
index cc1edab2..c507b2c4 100644
--- a/tests/utils/constraints.txt
+++ b/tests/utils/constraints.txt
@@ -8,6 +8,7 @@ cryptography >= 1.3.0, < 3.4 ; python_version < '3.6' # cryptography 3.4 drops s
 urllib3 < 1.24 ; python_version < '2.7' # urllib3 1.24 and later require python 2.7 or later
 wheel < 0.30.0 ; python_version < '2.7' # wheel 0.30.0 and later require python 2.7 or later
 paramiko < 2.4.0 ; python_version < '2.7' # paramiko 2.4.0 drops support for python 2.6
+paramiko < 3.0.0 ; python_version < '3.7' # paramiko 3.0.0 forces installation of a too new cryptography
 requests < 2.20.0 ; python_version < '2.7' # requests 2.20.0 drops support for python 2.6
 requests < 2.28 ; python_version < '3.7' # requests 2.28.0 drops support for python < 3.7
 virtualenv < 16.0.0 ; python_version < '2.7' # virtualenv 16.0.0 and later require python 2.7 or later