Troubleshooting email connection and delivery issues
The instructions below are for desktops and laptops only.
If you experience problems connecting an email inbox or sending and receiving emails through tawk.to, this guide explains the most common causes and how to resolve them.
Troubleshoot connection errors
When you connect an email inbox, tawk.to tests the incoming (IMAP) and outgoing (SMTP) connections separately. If either test fails, an error message identifies which connection needs attention.
Incorrect email or password
This is the most common connection error.
If your email account uses two-factor authentication (2FA), you'll usually need an app password instead of your regular account password. Providers such as Gmail, Outlook, Yahoo, and iCloud require app passwords for IMAP and SMTP connections.
To learn more, see this guide:
Creating an app password for your email account
If you're already using an app password, make sure IMAP is enabled for your email account if your provider requires it.
To learn more, see this guide:
Enabling IMAP access with your provider
Incoming (IMAP) connection failed
Verify that:
If you need to find your provider's server settings, see this guide:
Finding your email server settings
Outgoing (SMTP) connection failed
Verify that:
Many email providers use different port numbers for IMAP and SMTP, so confirming the incoming settings doesn't guarantee the outgoing settings are correct.
To learn more, see this guide:
Finding your email server settings
This email address is already connected
An email address can only be connected once within a workspace.
If the address is already connected, disconnect the existing inbox before connecting it again. If it's connected to another workspace, disconnect it there first.
Incorrect email or password
This is the most common connection error.
If your email account uses two-factor authentication (2FA), you'll usually need an app password instead of your regular account password. Providers such as Gmail, Outlook, Yahoo, and iCloud require app passwords for IMAP and SMTP connections.
To learn more, see this guide:
Creating an app password for your email account
If you're already using an app password, make sure IMAP is enabled for your email account if your provider requires it.
To learn more, see this guide:
Enabling IMAP access with your provider
Incoming (IMAP) connection failed
Verify that:
- The IMAP server address is correct.
- The port number is correct.
- The selected SSL/TLS encryption matches your provider's requirements.
If you need to find your provider's server settings, see this guide:
Finding your email server settings
Outgoing (SMTP) connection failed
Verify that:
- The SMTP server address is correct.
- The SMTP port number is correct.
- The SSL/TLS encryption settings are correct.
Many email providers use different port numbers for IMAP and SMTP, so confirming the incoming settings doesn't guarantee the outgoing settings are correct.
To learn more, see this guide:
Finding your email server settings
This email address is already connected
An email address can only be connected once within a workspace.
If the address is already connected, disconnect the existing inbox before connecting it again. If it's connected to another workspace, disconnect it there first.
Troubleshoot disconnected inboxes
If a connected inbox loses its connection, tawk.to marks it as Disconnected and displays the reason.
Sign-in failed
Authentication with your email provider failed.
This usually happens because:
Update your credentials and reconnect the inbox.
Can't reach server
tawk.to couldn't connect to your email provider's server.
This is often a temporary issue, and tawk.to continues trying to reconnect automatically.
If the problem continues:
Sign-in failed
Authentication with your email provider failed.
This usually happens because:
- Your mailbox password was changed.
- An app password was revoked.
- An app password expired.
Update your credentials and reconnect the inbox.
Can't reach server
tawk.to couldn't connect to your email provider's server.
This is often a temporary issue, and tawk.to continues trying to reconnect automatically.
If the problem continues:
- Check whether your email provider is experiencing an outage.
- Verify that your server addresses and port numbers are still correct.
Reconnect a disconnected inbox
2. Click Administration on the left navigation bar.
3. Select Integrations > Email (IMAP + SMTP).
4. Find the disconnected inbox and click Reconnect.
5. Update your password or app password if necessary.
6. Verify the IMAP and SMTP settings.
7. Complete the connection test.
Reconnecting preserves your:
Reconnecting doesn't create a new inbox or remove any existing conversations.
- Conversation history
- Inbox name
- Visibility settings
- Ownership
Reconnecting doesn't create a new inbox or remove any existing conversations.
Troubleshoot email delivery failures
Sometimes an email is sent successfully from tawk.to but can't be delivered by the recipient's email server.
When this happens, the conversation displays either:
Select View details to see the technical response returned by the recipient's mail server.
Common delivery reasons include:
When this happens, the conversation displays either:
- Delivery failed — {reason}
- Delivery delayed — {reason}
Select View details to see the technical response returned by the recipient's mail server.
Common delivery reasons include:
| Reason | What it usually means |
|---|---|
| Address not found | The email address doesn't exist, often because of a typo. |
| Blocked by recipient server | The recipient's server rejected the message, often because of spam filtering or security policies. |
| Server temporarily unavailable | The recipient's email server is temporarily unavailable. Delivery is usually retried automatically. |
| Message too large | The email, including attachments, exceeds the recipient's size limit. |
| Authentication or routing problem | The message couldn't be authenticated or routed correctly. Contact your email provider if the problem continues. |
| Other / Unclassified | The server returned a response that couldn't be categorized. Select View details to see the complete server response. |
Note: Delivery failures are reported by the recipient's email server. They don't indicate a problem with your connection to tawk.to, and other emails can continue to be sent normally.
Common problems
| If you see... | Try this... |
|---|---|
| “Incorrect email or password”, even though it's correct | If two-factor authentication is enabled, use an app password instead of your regular password. |
| The inbox disconnected unexpectedly | Update your mailbox password or app password, then reconnect the inbox. |
| Incoming mail works but outgoing mail fails | Verify your SMTP server address, port number, and encryption settings. |
| Your provider isn't listed | Select Custom / Other and enter your provider's IMAP and SMTP settings manually. |
| A reply appears to have been sent but never arrived | Make sure the sender didn't close the browser tab before the Undo Send countdown finished. |
| Email stopped arriving, but the inbox is still connected | Confirm that new email is arriving in the mailbox itself. If it is, contact tawk.to support. |
Additional considerations
- Use a dedicated app password
If your email provider requires an app password, create one specifically for tawk.to. This allows you to revoke or replace it later without affecting your other devices or applications.
- Temporary server issues often resolve themselves
If your settings haven't changed, wait a few minutes before making configuration changes.
- Check your provider's service status
If several inboxes from the same email provider disconnect at the same time, the issue may be with the provider rather than your tawk.to configuration.
Related guides
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