Troubleshoot a support mailbox

A support mailbox that stops working shows it in Settings > Mailboxes, in the Health column, and raises an alert. Select Test on the mailbox’s row first: the test runs each check in order and names the one that fails, which rules out most of this page.

Symptom

The Health column shows one of these, with a reason under it:

Status	Meaning
Connected	The last check for mail worked.
Needs attention	Outpost cannot reach the mail service. It keeps retrying.
Reconnect needed	The mail service refused Outpost’s sign-in or access. Nothing is collected until you reconnect.
Waiting for first sync	The mailbox is new and has not been checked yet.
Off	The mailbox is turned off.

Last mail received shows when the last message arrived, and Last checked when Outpost last looked, with the error from that check if it failed.

These alerts appear under the service desk’s alerts, named by the mailbox’s address:

Alert	Severity	Raised when	Clears when
address needs to be reconnected	Critical	The mailbox shows Reconnect needed.	The mailbox is connected again.
address is not syncing	Warning	Three checks in a row failed.	The next check works.
address has not synced in over 30 minutes	Warning	No check has worked for 30 minutes.	The next check works.
The daily test message to address did not arrive	Warning	The daily check message did not arrive within 2 hours.	The next daily message arrives.
The connection to address expires soon	Warning	A sign-in expires within 14 days.	The sign-in is renewed.
Held mail for address is waiting for review	Info	50 or more messages are in Suspended mail.	Fewer than 25 remain.

See Alerts.

The daily check

Once a day, Outpost sends a message with the subject Outpost mailbox check to each mailbox that is on, through the same path replies use, and watches for it to arrive. A forwarding mailbox gets it at its real address, so the check travels through your forwarding rule. The check message is never turned into a ticket. It is skipped while the mailbox shows Reconnect needed.

The check catches what a sign-in check cannot: a mail rule that diverts messages, a filter that quarantines them, or forwarding that someone turned off.

Check first

1. Select Test on the mailbox’s row. Read the first check that shows Failed and its message. Details shows the mail service’s own error.
2. Check that the mailbox still exists and that its address has not changed.
3. Check Suspended mail. Mail that arrives but is held does not show as a ticket, and the mailbox stays Connected.

Cause: the sign-in stopped working

The mailbox shows Reconnect needed with The sign-in stopped working. or The mail service refused access to the mailbox. Common reasons:

• The account’s password changed, for IMAP or a sign-in as the mailbox.
• An admin revoked the account’s sessions, or the sign-in expired.
• An admin removed the Outpost Mail app’s approval or its access to the mailbox in Microsoft 365, or the domain-wide delegation in Google Workspace.
• The client secret or service account key of your own app expired.

How to confirm it

Test fails at Sign in, with The sign-in expired or was revoked., The mail server refused the username or password., or Google has not authorized Outpost for this domain.

Resolution

1. Select Reconnect on the mailbox’s row. The wizard opens at its Connect step.
2. Connect again the same way: approve the app, sign in, or enter the new password, secret, or key.
3. Run the test.

Outpost picks up where it stopped. Mail that arrived while the mailbox was disconnected still becomes tickets, up to 14 days back.

Cause: the mail service cannot be reached

The mailbox shows Needs attention with The mail server could not be reached. or Outpost could not reach its mail service. It keeps retrying.

How to confirm it

Test fails at Connect with Could not reach the mail server.

Resolution

For IMAP, check the server name and port, and that your Outpost can reach the server through any firewall. For Microsoft 365, Google Workspace, and forwarding, wait: Outpost retries on its own, and the status returns to Connected when a check works. If it lasts more than an hour, see getting help.

The provider is limiting requests. Outpost slows down and retries. is not a failure. The provider asked Outpost to slow down, and it does.

Cause: the daily check message did not arrive

The daily test message alert is open. The mailbox can still show Connected, because signing in and checking for mail still work.

How to confirm it

Test passes Send a test message but Receive the test message shows The test message has not arrived.

Resolution

Something between sending and the inbox is holding the message:

• A mail flow rule, inbox rule, or filter moves or deletes it. Check the mailbox’s rules.
• A mail filter in front of the mailbox, such as Mimecast, Proofpoint, or Barracuda, quarantines it. Allow the support address as a sender in the filter.
• For a forwarding mailbox, the forwarding rule was removed, or Microsoft 365 now blocks external forwarding. See Forward email to Outpost.

Cause: Microsoft 365 access is not limited

A Microsoft 365 app connection fails Access limited to this mailbox with Outpost Mail can still reach other mailboxes in your organization. The mailbox stays off until the check passes.

Resolution

Run the access script from the wizard as an Exchange admin, wait 30 minutes to 2 hours for Microsoft to apply it, and test again. See Connect a Microsoft 365 mailbox.

Cause: replies stopped sending

Mail still becomes tickets, but replies do not arrive and Send a test message fails.

Resolution

• The server refused SMTP sign-in. Microsoft 365 turns SMTP AUTH off by default. Connect the mailbox with the Microsoft 365 app connection.
• For a mailbox that sends through Settings > Email, check the active provider’s Last test. See Configure outgoing email.
• A ticket marked Unverified sender sends nothing by design until a technician selects Verify sender. See Sender verification.

Still stuck

Collect these before asking for help:

• The mailbox’s address and how it is connected, from the Connection column.
• The result of Test, with each check’s message and Details.
• The Health reason and the open alerts.
• What changed most recently: a password, a policy, a DNS record, or a mail rule.

Then see getting help.