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generate_and_send_reminder_mail marked a reminder as "sent" before attempting SMTP send/IMAP append. If the connection, login, or append failed, the reminder stayed persisted as sent even though no mail was ever delivered or filed, so it could not be corrected and resent. Wrap content generation, archiving, and delivery in a try/except that calls the existing revert_reminder_sent on any failure and re-raises, putting the reminder back into "draft" for all three delivery modes.