STARTTLS command

-STARTTLS command establishes a secure communication session with email server, similarly to -SSL.

STARTTLS gets the information whether encrypted session is compatible with the server. Then, secured session is established right before transferring any sensitive data, such as credentials and message text itself. On the other hand, SSL establishes secure communication channel before sending any bits of information to the SMTP server.

Command syntax:
  • febootimail -STARTTLS

The default port for TLS connection is 25. Usually -STARTTLS parameter is used with server authentication commands -AUTH, -USER and -PASS.

C:\>febootimail -SERVER -FROM -TO -USER john -PASS 3kr5$DrB -MSG Email sent through TLS enabled mail server -STARTTLS

Essentially, STARTTLS is very similar to SSL in general aspects. Some email clients uses SSL instead of STARTTLS.

Example of sending Gmail email using STARTTLS. See an additional instructions, if getting "Allow less secure apps" error message. Just replace with valid Gmail address:

C:\>febootimail -SUBJ "Gmail and STARTTLS" -SERVER -STARTTLS -AUTH PLAIN -USER -PASS *********** -FROM -TO -TEXT "This email is sent using Gmail's server. It is easy and secure!"

OpenSSL credit: This product includes software developed by the OpenSSL Project for use in the OpenSSL Toolkit. ( This product includes cryptographic software written by Eric Young (

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