Troubleshooting email connection and delivery issues
Yasir
Last Update 2 days ago
If a connected email inbox stops working, tawk.to marks it as disconnected and shows the reason. This article covers the messages you may see, what causes them, and how to get the inbox working again.
The connection test failed while connecting
The test checks incoming and outgoing separately, so the message tells you which side to fix.
- "Incorrect email or password": the most common cause by far. If your account uses two-factor authentication, you need an app password, not your normal password. Gmail, Outlook, Yahoo and iCloud all require one. See Creating an app password for your email account.
- Incoming (IMAP) failed: check the IMAP server address, the port, and that SSL/TLS matches what your provider specifies.
- Outgoing (SMTP) failed: check the same details for the SMTP server. Many providers use a different port for outgoing mail, so a correct IMAP setup does not guarantee a correct SMTP one.
- The address is already connected: this email address is already connected to this workspace. To use a different connection method, disconnect the existing connection first. If it is connected to a different workspace, disconnect it there first.
Messages you may see on a disconnected inbox
Sign-in failed Authentication to the server failed. This usually means the mailbox password changed, or an app password was revoked or expired. Update your credentials to reconnect.
Can't reach server tawk.to could not reach your mail server. This is usually temporary and tawk.to keeps retrying. If it persists, check whether your provider is reporting an outage, and confirm the server address and port are still correct.
Can't reach server tawk.to could not reach your mail server. This is usually temporary and tawk.to keeps retrying. If it persists, check whether your provider is reporting an outage, and confirm the server address and port are still correct.
Reconnect an inbox
- Click Administration on the left navigation bar.
- Click Integrations, then Email (IMAP+SMTP).
- Find the disconnected inbox and choose Reconnect.
- Re-enter your password, or app password. Check the incoming and outgoing server details are still correct.
- Confirm to run the connection test again.
Your conversation history, inbox name, visibility and ownership are all preserved.
Reconnecting does not create a new inbox or lose anything.
When a message doesn't reach the recipient
If a message you sent cannot be delivered, the recipient's mail server tells us why and the conversation shows a delivery notice in place of a silent failure. The headline reads Delivery failed - {reason} (or Delivery delayed - {reason} where the server intends to retry), followed by which recipient it applies to. Select View details for the technical response from the recipient's server.
The reasons you'll see:
The reasons you'll see:
| Reason | What it usually means |
|---|---|
| Address not found | The address does not exist at that domain - most often a typo. |
| Blocked by recipient server | Their server rejected the message, often as spam or by policy. |
| Blocked by recipient server | Their server rejected the message, often as spam or by policy. |
| Server temporarily unavailable | A temporary problem at their end; delivery is usually retried. |
| Message too large | The message, including attachments, exceeded the recipient's size limit. |
| Authentication or routing problem | The message could not be authenticated or routed - worth checking with your provider if it recurs. |
| Other / unclassified | The server gave a reason we could not categorise; View details has the raw response. |
| Other / unclassified | The server gave a reason we could not categorise; View details has the raw response. |
Note: a delivery failure is a report from the recipient's mail server, not a problem with your tawk.to connection. Your inbox stays connected and other messages continue to send normally.
Common problems
| What you see | What to do |
|---|---|
| "Incorrect email or password," but the password is right | Two-factor is almost certainly on. Generate an app password with your provider and use that instead. |
| The inbox disconnected on its own | Usually a changed mailbox password or a revoked app password. Update the password and Reconnect. |
| Incoming works, outgoing fails | Check the SMTP port specifically - providers commonly use a different one for outgoing mail. |
| Your provider isn't recognised | Enter the server settings manually from your provider's help pages. |
| A reply was sent but never arrived | Check whether the sender navigated away immediately after selecting Send - replies are held briefly before going out, so leaving the page inside that window can prevent sending. |
| Mail stopped arriving but the inbox shows as connected | Confirm mail is arriving in the mailbox itself at your provider, then contact support. |
Additional considerations
- App passwords expire or get revoked If you rotate credentials as a matter of policy, expect to update the password in tawk.to at the same time. Using a dedicated app password for tawk.to means you can revoke it without affecting your other apps.
- Temporary failures usually recover on their own "Can't reach server" often clears without action. Give it a little time before changing settings that were previously working.
- Check the provider's own status first If several inboxes from the same provider fail at once, the cause is more likely at the provider than in your settings.
Learn more
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