What ACME client are you using? Can you share the command/configuration?
(As a note: it would be easier to debug this if you shared your real domain name)
One thing I notice about this policy is that it would forbid issuance for the base domain. It's typical when requesting a wildcard certificate to request both *.example.com and example.com since the former won't cover the later. If you are doing that with this CAA policy the validation for example.com will fail because there is no issue allowing Let's Encrypt, just an issuewild which is not considered for this case because RFC 6844 says:
issuewild properties MUST be ignored when processing a request for a domain that is not a wildcard domain.
teste.winserver2019.my-domain.com.br isn't a wildcard hostname. Therefore, without an issue tag for letsencrypt.org, your CAA record will refuse certificates with this hostname, as @cpu already explained.
The typical wildcard certificate has *.example.com and example.com as domain names and uses dns-01 validation with both domain names. So you have to create two txt entries.
I don't know the options of traefik. And an automatic script requires that you manage your own dns server or your dns provider supports an API you can use.