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Here's some code that I use to clear Acquia varish via the Purge / Acquia purge modules when a pdf with the same name is uploaded. You could expand on this to clear the styles cache as well.
/**
* Implements hook_entity_update().
*/
function my_module_entity_update(EntityInterface $entity) {
$type = $entity->getEntityTypeId();
if ($type != 'file') ...
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Is this causing a bug for you, or are you just trying to understand how it works at all?
Making the token system integrate with the cache system happened very late in the Drupal 8 development cycle (see https://www.drupal.org/node/2528662).
Note that if that optional Token::replace(…, …, …, BubbleableMetadata $bubbleable_metadata = NULL) argument is not ...
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