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SQLMail is troublesome and the reason for many support calls.
Your biggest issue, in my opinion, is the security context that SQL Server Agent is running under. Test SQLMail using the Windows user ID that the SQL Server Agent runs under.
You must first provide SQLMail with the Outlook mail profile used to test the mail client configuration. To do so, go to Enterprise Manger, then Support Services folder, right click SQL Mail and choose Properties.
You must then provide the mail profile to SQL Server Agent. To do so, go to Enterprise Manager, then Management folder, right click SQL Agent and choose Properties.
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