diff --git a/roles/system_check/tasks/_placement.yml b/roles/system_check/tasks/_placement.yml
index aaf43b7..5910011 100644
--- a/roles/system_check/tasks/_placement.yml
+++ b/roles/system_check/tasks/_placement.yml
@@ -50,6 +50,9 @@
         esxi_hostname: "{{ hypervisor_cfg.node }}"
       register: system_check_esxi
       delegate_facts: true
+      until: system_check_esxi.ansible_facts is defined
+      retries: 3
+      delay: 10
       failed_when: false
       changed_when: false
       no_log: true
@@ -84,6 +87,9 @@
       community.vmware.vmware_datastore_info:
         cluster: "{{ hypervisor_cfg.cluster }}"
       register: system_check_cluster
+      until: system_check_cluster.datastores is defined
+      retries: 3
+      delay: 10
       failed_when: false
       changed_when: false
       no_log: true
@@ -132,6 +138,10 @@
         path: "{{ item.path }}"
         state: file
       register: system_check_media_files
+      # A missing file fails with status 404; a dropped vCenter connection fails with status None.
+      until: system_check_media_files is not failed or system_check_media_files.status is not none
+      retries: 3
+      delay: 10
       failed_when: false
       changed_when: false
       loop: "{{ system_check_datastores_needed | rejectattr('source', 'equalto', 'hypervisor.storage') | list }}"
diff --git a/roles/system_check/tasks/main.yml b/roles/system_check/tasks/main.yml
index 95a7b6a..d47b411 100644
--- a/roles/system_check/tasks/main.yml
+++ b/roles/system_check/tasks/main.yml
@@ -82,6 +82,11 @@
             name: "{{ hostname }}"
             folder: "{{ system_cfg.path if system_cfg.path | length > 0 else omit }}"
           register: system_check_vmware_check_result
+          until: >-
+            not system_check_vmware_check_result.failed
+            or (system_check_vmware_check_result.msg is search('non-existing VM'))
+          retries: 3
+          delay: 10
           failed_when: false
           changed_when: false
           no_log: true