In an effort to resolve this I am running out of options. I have tried entering the password directly into the database with a fail in the end after encryption took over.

I do notice what is happening though. DNN is displaying the character count of the encrypted password and not the actual password. So once the password is saved, after a through test of the SMTP, it is converted to encryption and displayed back to me as the character count of the encrypted password and not the actual password. How would I overwrite what is happening?

I'm resurrecting the thread.

Can someone explain that to me why when sending bulletins or testing SMTP Admin / Host server I don't get any errors but when I register a fake user or send them a change password notification I get the error of:

Message:The SMTP server requires a secure connection or the client was not authenticated. The server response was: SMTP authentication is required.

StackTrace:

at System.Net.Mail.RecipientCommand.CheckResponse(SmtpStatusCode statusCode, String response)
at System.Net.Mail.SmtpTransport.SendMail(MailAddress sender, MailAddressCollection recipients, String deliveryNotify, Boolean allowUnicode, SmtpFailedRecipientException& exception)
at System.Net.Mail.SmtpClient.Send(MailMessage message)
at DotNetNuke.Services.Mail.Mail.SendMailInternal(MailMessage mailMessage, String subject, String body, MailPriority priority, MailFormat bodyFormat, Encoding bodyEncoding, IEnumerable`1 attachments, String smtpServer, String smtpAuthentication, String smtpUsername, String smtpPassword, Boolean smtpEnableSSL)

I cannot understand the logic behind the behavior of such discrepancies.

Currently I'm on DNN 7.4.2.

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