Lucy provides a dependable method for delivering emails during security awareness training campaigns by utilizing a known SMTP relay. This feature allows organizations to route emails through their own SMTP server, ensuring high deliverability and maintaining trust as emails are sent from a recognized company domain.
Key Considerations for Using SMTP with Lucy:
Trust and Deliverability: By using the company’s SMTP server, Lucy helps overcome common deliverability issues associated with external email services and enhances trust, as the emails are sent from familiar domains.
Caution with Simulated Attacks: While it is possible to send simulated phishing attacks through the SMTP server, it is advisable to use a controlled, dedicated SMTP server for such activities. This prevents any risks associated with blacklisting, which could disrupt daily operations if the same server is used for regular business communications.
Configuration Requirements: Ensure that emails sent through the SMTP option originate strictly from the email address associated with the SMTP server. This alignment is crucial for the success of email delivery in your campaigns.
Configuration
Navigate to Settings -> Common System Settings -> SMTP Servers
Select "Add Server"
Lucy enables administrators to set up multiple SMTP server configurations, making it an ideal solution for managing email delivery across various customers in a multi-tenant environment.
Next, you will define the SMTP Mail Server parameters:
The Name of this specific SMTP Server
This feature supports data segregation, allowing you to make the SMTP server available to either all clients or restrict it to a specific client on your list.
This is the SMTP Host for your mail server; for example Microsoft Office is smtp.office365.com or NameCheap is mail.privateemail.com
This depends on your mail server, generally speaking, the most common ports for SMTP are:
25: Traditionally used for SMTP to transfer emails between servers. However, due to its vulnerability to spam and misuse, many ISPs block it for outgoing mail.
587: Recommended for submitting emails to be sent by a mail server, supporting encryption (STARTTLS). It's the preferred port for client-to-server communication.
465: Initially used for SMTPS (SMTP over SSL), it was deprecated but later revived for SMTP submissions over SSL encryption directly. Some servers still support this port for secure submissions.
SSL/TLS
Usage: When an SMTP server uses SSL/TLS, it usually listens on a dedicated port (default is port 465) for secure connections.
Behavior: As soon as the connection is established, the server begins the SSL/TLS handshake to negotiate the encryption before any SMTP communication starts.
Security: The entire session is encrypted, meaning that no part of the email (including headers, body, or attachments) is sent in plain text.
Client Expectation: The email client must be configured explicitly to connect using SSL/TLS and to use the appropriate port.
STARTTLS
Usage: STARTTLS is an SMTP command that tells the server to switch from an unencrypted connection to a secure connection using SSL/TLS encryption.
Behavior: The SMTP server starts by listening on a non-encrypted port (usually port 25 or 587), and after the initial plaintext communication, either the client or server can issue the STARTTLS command to upgrade to a secure connection.
Security: The session starts unencrypted, but after the STARTTLS command is issued and the subsequent handshake, the communication is encrypted.
Client Expectation: The email client can begin communication on a standard SMTP port and then switch to an encrypted connection without needing to reconnect.
Choose "OAuth2" (e.g., Azure) if your mail server supports this authorization framework. Alternatively, you can select "Password authentication," which requires the administrative username and password for authentication.
For example, I would like to authenticate to my NameCheap SMTP server. The Hostname for all NameCheap SMTP servers is - mail.privateemail.com; the port is 587; and I will be authenticating with my administrative username and password:
Once completed, click Save to commit your SMTP server settings.
Test Your Connection:
To test your SMTP server settings, simply enter the sender email address (which must be the exact email address associated with your SMTP server) and a recipient email address you have access to. Then, click or select "Test" to initiate the testing process.
This will provide you with an output:
If you encounter any errors, look at the error status code for further troubleshooting.
SMTP Error Status Codes
connect
220 domain Service ready
421 domain Service not available, closing transmission channel
HELO
250 Requested mail action okay, completed
500 Syntax error, command unrecognised
501 Syntax error in parameters or arguments
504 Command parameter not implemented
521 <domain> does not accept mail [rfc1846]
421 <domain> Service not available, closing transmission channel
EHLO
250 Requested mail action okay, completed
550 Not implemented
500 Syntax error, command unrecognized
501 Syntax error in parameters or arguments
504 Command parameter not implemented
421 <domain> Service not available, closing transmission channel
MAIL
250 Requested mail action okay, completed
552 Requested mail action aborted: exceeded storage allocation
451 Requested action aborted: local error in processing
452 Requested action not taken: insufficient system storage
500 Syntax error, command unrecognized
501 Syntax error in parameters or arguments
421 <domain> Service not available, closing transmission channel
RCPT
250 Requested mail action okay, completed
251 User not local; will forward to <forward-path>
550 Requested action not taken: mailbox unavailable
551 User not local; please try <forward-path>
552 Requested mail action aborted: exceeded storage allocation
553 Requested action not taken: mailbox name not allowed
450 Requested mail action not taken: mailbox unavailable
451 Requested action aborted: local error in processing
452 Requested action not taken: insufficient system storage
500 Syntax error, command unrecognized
501 Syntax error in parameters or arguments
503 Bad sequence of commands
521 <domain> does not accept mail [rfc1846]
421 <domain> Service not available, closing transmission channel
DATA
354 Start mail input; end with <CRLF>.<CRLF>
451 Requested action aborted: local error in processing
554 Transaction failed
500 Syntax error, command unrecognized
501 Syntax error in parameters or arguments
503 Bad sequence of commands
421 <domain> Service not available, closing transmission channel
received data
250 Requested mail action okay, completed
552 Requested mail action aborted: exceeded storage allocation
554 Transaction failed
451 Requested action aborted: local error in processing
452 Requested action not taken: insufficient system storage
RSET
200 (nonstandard success response, see rfc876)
250 Requested mail action okay, completed
500 Syntax error, command unrecognized
501 Syntax error in parameters or arguments
504 Command parameter not implemented
421 <domain> Service not available, closing transmission channel
SEND
250 Requested mail action okay, completed
552 Requested mail action aborted: exceeded storage allocation
451 Requested action aborted: local error in processing
452 Requested action not taken: insufficient system storage
500 Syntax error, command unrecognized
501 Syntax error in parameters or arguments
502 Command not implemented
421 <domain> Service not available, closing transmission channel
SOML
250 Requested mail action okay, completed
552 Requested mail action aborted: exceeded storage allocation
451 Requested action aborted: local error in processing
452 Requested action not taken: insufficient system storage
500 Syntax error, command unrecognized
501 Syntax error in parameters or arguments
502 Command not implemented
421 <domain> Service not available, closing transmission channel
SAML
250 Requested mail action okay, completed
552 Requested mail action aborted: exceeded storage allocation
451 Requested action aborted: local error in processing
452 Requested action not taken: insufficient system storage
500 Syntax error, command unrecognized
501 Syntax error in parameters or arguments
502 Command not implemented
421 <domain> Service not available, closing transmission channel
VRFY
250 Requested mail action okay, completed
251 User not local; will forward to <forward-path>
550 Requested action not taken: mailbox unavailable
551 User not local; please try <forward-path>
553 Requested action not taken: mailbox name not allowed
500 Syntax error, command unrecognized
501 Syntax error in parameters or arguments
502 Command not implemented
504 Command parameter not implemented
421 <domain> Service not available, closing transmission channel
EXPN
250 Requested mail action okay, completed
550 Requested action not taken: mailbox unavailable
500 Syntax error, command unrecognized
501 Syntax error in parameters or arguments
502 Command not implemented
504 Command parameter not implemented
421 <domain> Service not available, closing transmission channel
HELP
211 System status, or system help reply
214 Help message
500 Syntax error, command unrecognized
501 Syntax error in parameters or arguments
502 Command not implemented
504 Command parameter not implemented
421 <domain> Service not available, closing transmission channel
NOOP
200 (nonstandard success response, see rfc876)
250 Requested mail action okay, completed
500 Syntax error, command unrecognized
421 <domain> Service not available, closing transmission channel
