Connecting Email

Know Reply supports multiple ways to connect an inbox. Choose the method that fits your setup.

If you would rather not hand over mailbox credentials, you can delegate a reply subdomain instead. See the reply domain guides.

Each agent needs its own dedicated email account

Every agent must have a dedicated email address that it owns exclusively (e.g. support@yourdomain.com, hello@yourdomain.com). This is the reply-to address on your outgoing emails — when customers reply to your campaigns, newsletters, or transactional emails, those replies land in this inbox and the agent handles them automatically.

Do not use a personal or shared mailbox. The agent monitors and responds to every message in its connected inbox. Create or designate a separate email account for each agent before connecting.

Gmail (OAuth)

The recommended method for Gmail accounts. Secure, no passwords stored.

1. In your agent settings, click Connect Email
2. Choose Google
3. Click Connect Now
4. Sign in with the dedicated Google account for this agent
5. Grant the requested permissions

Know Reply begins monitoring the inbox within minutes.

Microsoft 365 (OAuth)

For organizations using Outlook or Microsoft 365:

1. Click Connect Email
2. Choose Outlook
3. Click Connect Now
4. Sign in with your Microsoft work account
5. An admin may need to approve the app permissions in Azure AD the first time

After consent, the agent syncs and begins processing.

IMAP / SMTP

For providers that don’t support OAuth (Zoho, Fastmail, Yahoo, custom domains):

1. Click Connect Email and choose SMTP/IMAP
2. Fill in the connection details:

Field	Description	Example
Email Address	The inbox to monitor	support@example.com
Username	Usually same as email	support@example.com
Password	Your email password, or an app password for Gmail, Yahoo, and iCloud
IMAP Host	Incoming mail server	imap.gmail.com
IMAP Port	Usually 993 for SSL	993
SMTP Host	Outgoing mail server	smtp.gmail.com
SMTP Port	Usually 587 or 465	587

Gmail, Yahoo, and iCloud require an app password

These providers don’t accept your normal login password over IMAP/SMTP. First turn on 2-Step Verification on the account, then generate an app password and use that 16-character code in the Password field above.

• Gmail: enable 2-Step Verification, then create an app password. Personal @gmail.com accounts only. If it’s a Google Workspace account and the option is missing, your Workspace admin has disabled app passwords; ask them to enable app passwords for your account (Google Admin console) so you can connect over IMAP/SMTP.
• Yahoo / iCloud: generate an app password in the account’s security settings and use it as the password.

3. Click Test Connection to verify both inbound and outbound
4. Click Add Account to save

Common provider settings

Provider	IMAP Host	SMTP Host
Gmail	imap.gmail.com (993)	smtp.gmail.com (465)
iCloud	imap.mail.me.com (993)	smtp.mail.me.com (587)
Zoho Mail	imap.zoho.com (993)	smtp.zoho.com (465)
Fastmail	imap.fastmail.com (993)	smtp.fastmail.com (465)
Yahoo	imap.mail.yahoo.com (993)	smtp.mail.yahoo.com (465)

ESP Webhooks

If you send through an ESP like Postmark, SendGrid, or Mailgun:

1. Click Connect Email and choose Webhook
2. Select your provider (Postmark, SendGrid, or Mailgun)
3. Enter your API key
4. For Mailgun, also enter your domain
5. Click Connect Now

In your ESP dashboard, set the provided webhook URL as the Inbound Webhook destination. Replies to your campaigns and transactional emails get forwarded to Know Reply automatically.

Switching connections

You can disconnect and reconnect at any time. Go to the email settings, click the connection, and choose Disconnect.