The disclosure herein describes providing transaction retry notifications to merchants based on monitored account usage. An insufficient funds message of a first transaction is received that indicates the first transaction includes a payment to be provided to a merchant from an account and that the account has insufficient funds for the first transaction. An account identifier of the account is stored and a transaction message of a second transaction associated with the account is detected based on the stored account identifier. The transaction message indicates that the account has sufficient funds for the second transaction. Based on detecting the transaction message, a transaction retry notification is sent to the merchant, whereby the merchant is notified that the account with which the first transaction is associated includes a quantity of funds. The disclosure enables merchants to optimize the timing or retrying failed transactions and thereby reduce costs associated with transaction retries.