Custom validation for paragraph field
As you mentioned, you'll need to add a custom validate function. Since this checkbox can be checked or unchecked on the fly, you will also need to use some javascript to toggle the "required" class on and off the textbox. This will make sure it looks right to the user. Of course you'll need to make sure you have a required class style in css.

This is just freehand, and just one way it could be done. You would need to adapt this to your fields.

create a custom module. In your .module file

&lt;?php
use Drupal\Core\Form\FormStateInterface;

function MYMODULE_form_alter(&amp;$form, \Drupal\Core\Form\FormStateInterface $form_state, $form_id) {
  //where CONTENTTYPE is the machine name of your content type
  if ($form_id == 'node_CONTENTTYPE_edit_form') {
    $form['#validate'][] = 'my_test_validate';
  }
}

function my_test_validate($form, FormStateInterface &amp;$form_state) {
  $checkbox = $form_state-&gt;getValue('field_my_checkbox');
  $textfield = $form_state-&gt;getValue('field_my_textbox');

  //if the checkbox is checked
  if ($checkbox['value'] == 1) {
    if (trim($textfield[0]['value']) == "" || empty($textfield)) {
      $form_state-&gt;setErrorByName('mytextfield', t('Text field blah blah is required'));
    }
  }
}


In a js file somewhere in your module or theme you could have something like:

(function ($, Drupal) {

  Drupal.behaviors.myForms = {
    attach: function (context, settings) {
      //add a click listener to toggle whatever styles you want
      $('#edit-field-mycheckbox-value').click(function(){
        $('#edit-my-textfield-0-value').toggleClass('required');
        $("label[for='edit-my-textfield-0-value']").toggleClass('form-required');
      //etc
      });


    }
  };

})(jQuery, Drupal);