Mailbox Reconnection — when and how to reconnect

When you see a Reconnect Required badge on a mailbox — or the Reconnect Required banner on the dashboard — sending from that mailbox is blocked until you take action. This page explains exactly when WarmySender flags a mailbox for reconnection, what you should do, and what happens in the meantime.

When does a mailbox need reconnection?

A mailbox is flagged for reconnection when any of these conditions are true:

What should I do?

• On the Mailboxes page, click the Reconnect Required badge or open the affected mailbox's menu. The action you'll be prompted to take depends on the provider:
- Gmail / Google Workspace: click Update credentials and paste a fresh App Password — Gmail connects with an App Password over IMAP/SMTP, not a Google sign-in. App Passwords are often invalidated by a password change or a security review. Generate a new one at myaccount.google.com/apppasswords (2-step verification must be on) and save. This typically takes a minute or two.
- Outlook / Microsoft 365: click Reconnect with Microsoft to re-grant OAuth, or if the error is 5.7.139, ask your M365 administrator to enable Authenticated SMTP for your mailbox (see /documentation/smtp-tenant-disabled for the admin steps).
- Custom IMAP/SMTP (Hostinger, Zoho, Yahoo, Fastmail, self-hosted, etc.): click Update credentials and paste a fresh password or App Password. For providers that require App Passwords (Gmail-via-SMTP, Yahoo, iCloud, Outlook personal accounts with 2FA), generate a new one from your provider's security settings and update the SMTP/IMAP password fields.

What happens in the meantime?

How long does reconnection take?

Note: WarmySender will never email you to reconnect a mailbox — the in-app surface is the source of truth. If you're worried about phishing, anyone asking you to "reconnect your mailbox" via email is not us. Always open warmysender.com directly to take action.

Back to all documentation | Contact support