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Attachment Reminder is an Add-On (extension) for Mozilla Thunderbird that scans outgoing email for user-defined keywords (or just use the default list), and prompts you if it looks like you wanted to attach a file but didn't.
MMReencrypt is an add-on for Mailman. It allows reencrypting mailing lists for added security. Users post messages PGP- or GPG-encrypted to the list's public key. MMReencrypt decrypts them, then re-encrypts the message to each subscriber.