Hi @Rick Maskey
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If every Windows 11 PC running Outlook Classic repeatedly switches between Connected and Disconnected, and messages remain stuck in the Outbox, it often means the Microsoft 365 subscription has expired. When a subscription lapses, Exchange Online disables mailbox access, preventing Outlook from connecting. In this state, Outlook shows Disconnected, and emails will stay in the Outbox until the subscription is renewed.
You may want to ask your administrator to verify that your subscription license is still active. If it is expired, renew the subscription immediately in the Microsoft 365 Admin Center. Once the subscription is active again, Outlook will reconnect automatically.
I hope this helps.
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