If the previous task before the copy one is to install some features and 
reboot then potentially the WinRM service comes back online but it reboots 
one more time that isn't caught. What I would potentially do is


- name: install problematic features
  win_feature:
    name: ...
  register: feature_install


- name: reboot after feature install
  win_reboot:
  when: feature_install.reboot_required


- block:
  - name: copy file
    win_copy:
      src: files/certs/mycert_2020.pfx
      dest: C:\scripts\


  rescue:
  - name: copy failed wait for connection to become stable
    wait_for_connection:


  - name: copy the file again
    win_copy:
      src: files/certs/mycert_2020.pfx
      dest: C:\scripts\


- name: run setup script
  script: files/certs/install_cert.bat
  args:
    creates: c:\scripts\certinstalled.txt


The block/rescue may not work as the failure happened in the connection 
plugin and not the module and this usually is a fatal exception that is not 
recoverable. But because win_copy is an action plugin it may work I just 
can't confirm right now. If it doesn't work then you may need to look into 
the logs a bit more to see why it may be rejecting your credentials or as a 
precaution put a pause after the win_reboot step and then 
wait_for_connection straight after to try and catch these exceptions.

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