TryNow will re-authorize a card if the merchant is not on Shopify Plus, the shopper used Discover, or the order lifecycle exceeded 30 days.
Shopify Plus has access to extended authorizations through Shopify Payments, but Shopify standard merchants do not
Discover cards only have access to 7 day authorization windows
Therefore, TryNow refreshes the authorization when it expires, but it can take 24-48 hours for the expired authorization to drop from the shopper's statement. As such, shoppers may see multiple authorizations, but there will only ever be one active authorization per trial order at a time.
For a full list of Shopify's authorization periods, please refer to the table below and article here.