Swaks

Github: https://github.com/jetmore/swaks

Send email

swaks --to [e-mail] --from [e-mail] --header "Subject: WHATEVER" --body "WHATEVER" --server TARGET_IP --attach @MALICIOUS_FILE

Send email with authentication

swaks -t <[e-mail]> --from <[e-mail]> \ --attach config.Library-ms --server <SMTP_SERVER> --body body.txt \ --header "Subject: Problems" --suppress-data \ --auth LOGIN --auth-user <username> --auth-password <password>

Email with Custom Headers for Social Engineering

swaks -t [target-email] --from [your-email] --attach [file-to-attach] \ --server [smtp-server-ip] --body [email-body.txt] \ --header "X Priority: 1 (Highest)" --header "Importance: High" --suppress-data