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Estou tendo problemas com a emissão automática de NF no WooCommerce 9.0.1 (HPOS ativado e modo compatibilidade desativado).
Fiz alguns testes e parece que o hook transition_post_status não é executado quando ocorre a mudança de status. Não tenho certeza se pode ser algo exclusivo do meu setup.
Tentei alterar para o hook woocommerce_order_status_changed, fazendo as devidas modificações no código, e aí deu certo.