WordPress is not sending the 2nd email in the same request

The issue was not caused by WordPress. It was caused by a plugin.

In this particular case, I checked the plugins installed looking for anything that could modify the mail behavior. I disabled the plugin “Email Templates” and started receiving all the messages normally. Then I noted that there was an update available for that plugin, I applied the update, tested again and it was working as expected.

So, in summary, the issue was caused by an outdated plugin.