I have software that allows me to email estimates statements bills etc. Using Gmail is flawless. When I try to use Outlook Office365 or GoDaddy workspace all I get is "Timeout" or "The SMTP server requires a secure connection or the client was not authenticated. the server response was: 5.7.57; Clent was not authenticated to send anonymous mail during MAIL FROM [MN2PR20CA0009.namprd20.prod.outlook.com]"
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