Emails Stuck in the Outbox in Airmail for macOS – How to Send or Recover Them

If one or more messages remain in the Outbox and are not sent, they usually have not left your Mac yet, so in most cases they can still be sent or recovered. This guide explains what to check.
Why messages get stuck in the Outbox: a message stays in the Outbox when Airmail is unable to hand it to the outgoing (SMTP) server. The most common reasons are a temporary loss of internet connection, the account needing to sign in again, or the app being quit before the message finished sending.
Step 1 – Open the Outbox. In the folder list on the left, open the Outbox. Every message that failed to send is listed here, and nothing is lost as long as it appears in this folder.
Step 2 – Check your connection and account. Make sure your Mac is online, then open Airmail Settings > Accounts and confirm the account is connected and is not asking you to sign in again. If it prompts you to re-authenticate, complete the sign-in.
Step 3 – Send the messages again. Open each message in the Outbox and press Send again. When the connection and account are active, the messages will be delivered and moved to the Sent folder.
Step 4 – Confirm what was actually sent. To be sure which messages went out, sign in to your email provider on the web (for example Gmail or Yahoo) and open the Sent folder. Anything that truly sent will appear there, which helps you avoid sending duplicates.
If messages disappear from the Outbox: check the Drafts folder, where an unsent copy may have been saved. You can reopen it from Drafts and send it again.
Still need help? If the messages are not in the Outbox, Drafts, or your provider's Sent folder, contact us and include your Airmail version (Airmail > About Airmail) and your macOS version so we can investigate further.
Note: Airmail for Mac is distributed through the Mac App Store and runs in a sandboxed environment. The steps above only use options inside the app and your account settings, so no advanced or system-level changes are required.

Updated on: 07/10/2026