Try starting the necessary services multiple times.

tasks/general/software/services.yml

@@ -9,6 +9,10 @@
     pattern: "{{ crond_pattern }}"
     state: started
     enabled: yes
+  register: cron_status
+  until: cron_status.state == "started"
+  retries: 3
+  delay: 3
 
 
 ## CUPS ##
@@ -76,6 +80,10 @@
     pattern: "{{ sshd_pattern }}"
     state: reloaded
     enabled: yes
+  register: sshd_status
+  until: sshd_status.state == "started"
+  retries: 3
+  delay: 3
 
 
 ## JournalCTL ##
@@ -105,3 +113,7 @@
     pattern: "{{ ntp_server }}"
     state: started
     enabled: yes
+  register: ntp_status
+  until: ntp_status.state == "started"
+  retries: 3
+  delay: 3