When an email reply is not delivered
What the red line under a reply means, the reasons a reply is refused or bounces, how you are told, and what to check before sending again.
On this page
When a reply cannot reach the customer, the ticket says so under the message itself, in red, with the reason. The agent who sent it also gets an email about it. Nothing is retried in a way that could send the customer two copies.
What you see on the ticket#
| Line under the reply | Meaning |
|---|---|
| Sending | The reply is on its way to the mailbox. |
| Not sent: and a reason | The helpdesk or the mail service refused it. The customer did not get it. |
| Delivery problem: and a reason | It left the helpdesk, but the customer's mail server bounced it, or the customer marked it as spam. This applies to forwarded addresses, where the helpdesk hears back from the mail service. |
The agent who wrote the reply gets an email that names the reason and links to the ticket, unless they switched off A reply I sent could not be delivered in Settings > Notifications. It is on for everyone by default. See Notifications.
Reasons and what to do#
| Reason shown | What happened | What to do |
|---|---|---|
| The mailbox needs to be reconnected | Google stopped accepting the mailbox's connection. | An admin clicks Reconnect in Settings > Email. The waiting reply is sent then, with no need to write it again. |
| No connected mailbox can send this message | The ticket's mailbox was disconnected and no other is connected. | Connect a mailbox or set up forwarding, then send the reply again. |
| The attachments add up to more than 25 MB | Gmail and the helpdesk do not send more than 25 MB in one message. | Send fewer or smaller files, or link to them. |
| The message has no recipient | The ticket's customer has no email address, and none was typed in To. | Add the address to the customer or in the reply. |
| One of the attachments is no longer stored | A file was removed before the reply went out. | Upload it again. |
| Gmail refused this message, or Resend refused this message | The mail service rejected it, usually because of a bad address or attachment. | Check the recipients and attachments, then send it again. |
| The recipient's mail server refused this reply (permanent bounce) | The address does not exist or will not accept mail. | Check the spelling with the customer through another channel, or ask them for another address. |
| The recipient's mail server did not accept this reply (temporary bounce) | Their mailbox is full or their server is busy. | It may still arrive. If the customer says it did not, send it again later. |
| The recipient marked this reply as spam | Later mail to them may be filtered. | Ask the customer to look in their spam folder and mark you as safe. |
| The customer's last message was written by a machine | An automatic reply, bounce or newsletter came in, and rules never answer those. | Nothing; reply by hand if a person needs an answer. |
| Automated replies already went out 3 times on this ticket in the last hour | Rules are stopped from answering the same ticket over and over. | Check the rule that keeps replying. See Rules. |
| Gmail did not confirm the send | Gmail stopped answering partway through. | Look in the mailbox's Sent folder before sending it again, so the customer does not get it twice. |
When the mail service asks the helpdesk to slow down, or does not confirm a send, the helpdesk tries again on its own a few times. Each try is the same message, so the customer gets one copy at most.
Bounces on a Gmail mailbox#
Gmail delivers your replies and handles bounces itself: when the customer's server refuses a reply, Gmail sends a "Delivery Status Notification" back to your mailbox. That notice comes into the helpdesk like any mail, usually on the same ticket, tagged bounce. Read it for the reason, then correct the address.
The customer says they got nothing, and there is no red line#
Open the ticket and check the address in To on your reply.
Ask the customer to look in their spam and promotions folders.
For a Gmail mailbox, look for the reply in the mailbox's Sent folder.
For a forwarded address, remember that your reply comes from the helpdesk's forwarding address, with Reply-To set to your support address. A customer filtering by your address will not see it under that name. See how forwarded replies are sent.
Resend the answer, or reach the customer another way and confirm their address.
Replying outside the helpdesk#
Replies written in Gmail itself still reach the customer and join the ticket, but the helpdesk cannot report on their delivery: Gmail's own bounce notice is the only sign. Reply from the ticket where you can.
Related articles
- Connect a Gmail or Google Workspace mailboxConnect your support mailbox so its mail arrives as tickets within a minute and replies go out from Gmail in the customer's own thread.
- Forward a support address from any mail providerSet up forwarding from Outlook, Zoho or any other provider, see how replies are sent, and why no DNS records or domain verification are needed.
- NotificationsThe bell, the emails you can get about tickets and mentions, the daily summary of open tickets, and what admins set for new agents.
- Work a ticket from first read to closeReading the conversation and its events, the four ways to answer, Cc and attachments, sending, closing and reopening, and the spam, trash, print and link actions.
Still stuck?
Write to the Growth Dept team and a person answers. Say which helpdesk you work in and what you were trying to do.