The article "Fixed: Outlook Cannot Send This Item" on AssistMe360.com provides a comprehensive guide to resolving the common issue where Outlook fails to send emails. It covers various solutions, including checking email settings, ensuring the attachment size is within limits, and updating the Outlook application. The guide also suggests clearing the Outbox and restarting Outlook as simple initial steps. For more complex issues, it delves into adjusting add-ins and repairing the Outlook data file. This article is a valuable resource for anyone experiencing email sending problems in Outlook, offering step-by-step instructions to quickly restore functionality.