Configuring your Challo assistant mailbox

If you are using Microsoft Office 365 or Google Suite to manage an email domain for your organization, configure the mailbox of your Challo assistant.

In this article, the mailbox of the Challo assistant is:

  • casper is the primary alias of the mailbox.
  • The Challo assistant uses dynamic aliases to target tracks, in the following format: Challo assigns a unique value to alias for each track.
  • Your mail server forwards emails in this format to the mailbox of your Challo assistant.

If you do not configure an assistant mailbox, the CafeX assistant sends emails from when necessary.

Configuring Challo to connect to your mail server

As a tenant’s administrator, to setup the Challo assistant to use a mailbox:

  1. Create a mailbox for the assistant:
  2. From your Challo menu, click Tenant settings
  3. Click Email
  4. Complete the mailbox configuration for your assistant to use.
    Attribute Description
    Mailbox The mailbox identity of your Challo assistant. For example: casper
    Domain The domain of your Challo assistant’s mailbox. For example:
    Display Name the display name the assistant presents in the emails it sends. For example: Casper
    Mode Important: Unless Challo instructs you, set this to Unseen. The Challo assistant processes unread emails, before it marks them read.
  5. If you are configuring a Microsoft Office 365 suite, specify connection details for your Exchange Server:
    Attribute Description
    Password The mailbox password for your Challo assistant.
    Server The address of your IMAP email server. For example:
    Port The IMAP email server port. For example: 993
    SMTP Server The address of your SMTP server. For example:
    SMTP Port The port of your SMTP server. For example: 587
    SMTP Encryption The encryption method to use to connect to your SMTP Server.
    For Microsoft Exchange use: STARTTLS

    If you are configuring another Exchange server, these hostnames and ports must be accessible from Challo.
    See also:

  6. Alternatively, if you provide a SendGrid API key for outbound messages, emails that your Challo assistant sends originate from SendGrid. See: SendGrid—API keys
  7. Verify your Challo assistant
  8. Click Update

Configuring Microsoft Exchange Server for Challo

As a administrator, in your Exchange Server configure the following:

  1. Configure your mail flow settings for the Challo assistant
  2. Configure the assistant mailbox

Configuring the Microsoft Exchange mail flow rules

As a administrator, to create the mail flow rules that the Challo assistant uses to detects dynamic alias, configure the following: 

  1. To receive email from outside of your organization, set the accepted domain to use internal relay
    See: Managed accepted domains in Exchange Online
  2. Create a rule to forward emails to the mailbox of the Challo assistant with the following:
    Attribute Description
    Name The name of your Challo assistant mail flow rule.
    For example: Challo Assistant rule
    Apply this rule if… Set this to:
    The recipient address includes… The primary alias of your Challo assistant mailbox.
    For example: casper
    Do the following… Redirect the message to… Your Challo assistant

    See: Manage mail flow rules on Exchange Online

    For example:
    The mail flow rule for the mailbox for may appear as the following:

Challo assistant mailbox configuration

As an administrator, To allow Challo to read calendar events in the Challo assistant mailbox, enable the follow IMAP option:
Send event invitations in iCalendar format

See also: Microsoft—POP3 or IMAP4 Settings for a user

Verifying your assistant mailbox

After you fill in the mailbox settings, to verify that Challo can connect to your assistant mailbox, click Validate email config.

Challo uses the configuration you provide to:

  • Connect to the mailbox to check that Challo can read emails it receives.
  • Make a request to send an email from the mailbox. Challo does not verify that it receives the email, only that the request to send an email is successful.

If the validation is not successful, there is an error message that Challo receives during the attempt to connect to the mailbox.