Email servers (SMTP and IMAP)

An email profile connects Kareenos to one mailbox on your own mail server. An SMTP profile lets agents send from that address. An IMAP profile watches that mailbox and wakes an agent whenever new mail arrives. You can add as many of each as you need, and you name every one of them, because that name is how an agent asks for it.

Where to find it#

Press Open in Kareenos above to open the Connectors tab, then scroll to the Email Servers (SMTP / IMAP) section, or open the avatar menu, choose Settings, then Connectors. Administrators only.

Name profiles the way you would label a drawer#

Agents choose a profile by name, so the name is functional, not decorative. Good names describe the mailbox and what it is for: support-mailbox, billing-sender, orders-inbox. If you only have one active profile of a kind, agents will use it without being told which. Once you have several, the name is the only way anyone can be precise.

The profile name cannot be changed after you create it, and neither can the protocol. Pick both deliberately.

Step by step: adding a profile#

1. Open Connectors and press Add profile in the Email Servers section.

2. Choose the protocol at the top of the dialog: SMTP, send email or IMAP, watch an inbox.

   

3. Fill in the Profile name and, optionally, a Description. The description is shown to agents when they are choosing between profiles, so write it for them.

4. Fill in the server connection: Host, Port, Username and Password.

5. Set the encryption toggle. For SMTP it is implicit TLS on port 465, or off for STARTTLS on port 587 or plain on 25. For IMAP it is TLS on port 993, or off for plain or STARTTLS on 143.

6. Fill in the fields specific to the protocol, described below.

7. Press Test Connection. This works before you save, using whatever you have just typed.

8. Leave Active switched on and press Save.

SMTP profiles#

An SMTP profile adds a sender identity on top of the server connection.

Agents sending through an SMTP profile can reply inside an existing thread, so the customer sees one continuous conversation in their mail client rather than a series of unconnected messages.

IMAP profiles#

An IMAP profile adds the watching behaviour.

Allowing a self signed certificate#

There is a toggle for mail servers using a certificate that is not publicly trusted. Only use it for an internal server you run and can vouch for. On any server reachable from the internet, a certificate warning is information you want, not noise to switch off.

What happens after you save#

Sending has a daily ceiling for the whole organization, so a misbehaving agent cannot burn through your mail server's sending reputation overnight. Agents are told when they hit it and stop rather than retrying.

If an inbox check fails, because the password changed or the server moved, the profile shows a failure marker on its tile with the reason. Check the tab when incoming mail stops producing any reaction.

Microsoft 365#

Email profiles sign in with a username and password. Microsoft is withdrawing password based sending from business mailboxes in stages, so for a Microsoft 365 mailbox the durable route is a linked account, which uses Microsoft's normal sign in.

If you still want a profile, the settings are:

Two things have to be true on the Microsoft side first, and both are administrator jobs in the Microsoft 365 admin center:

1. Authenticated SMTP must be switched on for that specific mailbox, under Users, Active users, the user, Mail, Manage email apps. It is off by default in most tenants.
2. IMAP must be switched on for the mailbox in the same place.

A personal Outlook.com address is different from a Microsoft 365 business mailbox and no longer accepts a normal password for mail clients at all.

Microsoft's own pages: Enable or disable SMTP AUTH in Exchange Online, POP, IMAP and SMTP settings, and the announcement about retiring password based sending.

Google Workspace and Gmail#

The same reasoning applies. Google also prefers its own sign in and describes app passwords as a fallback rather than a recommendation, so a linked account is the better long term choice for a Gmail mailbox.

If you want a profile, the settings are:

Port 587 with STARTTLS also works for sending if your network blocks 465.

On the Google side, the account needs 2-Step Verification switched on, and you then generate an app password and paste that into the Password field instead of the normal account password. IMAP no longer needs to be enabled separately in Gmail. If you are on Google Workspace, your administrator can block app passwords for the whole organization, in which case a linked account is your only route.

Google's own pages: Sign in with app passwords and Add Gmail to another email client.

Any other mail server#

Everything else works the same way. Take the incoming and outgoing server details from your hosting provider or your IT team, use the standard ports above as a starting point, and let Test Connection confirm the combination before you save. A mail server you run yourself, a hosting provider's mailbox and an on premises Exchange server are all straightforward, and are the case these profiles were built for.

Common mistakes#

• Using the mailbox's display address as the username. Most servers want the full address, some want just the account name. Test both.
• Setting a From email the mailbox is not allowed to send as. The connection test passes and real sends still bounce.
• Switching a profile on and expecting the existing backlog to be processed.
• Leaving the check interval at one minute on a quiet mailbox, which achieves nothing except constant polling.
• Changing the mailbox password later and forgetting the profile. The tile will show the failure, but only if somebody looks.

Next#

• Choosing an email option
• Google and Microsoft accounts
• Transactional email