Dear Rick,
I am trying to use your example to sending a mail ("Sending SSL Email with wwSmtp"):

DO wwSmtp 

LOCAL loSmtp as wwSmtp
loSmtp = CREATEOBJECT("wwSmtp")

loSmtp.nMailMode = 0  && .NET Mode required

*** Google SMTP server - requires login and SSL/TLS
loSmtp.cMailServer = "smtp.office365.com:587"

*** Important for Secure SSL/TLS connections
loSmtp.lUseSsl = .T.

loSmtp.cUsername = MyEmail
loSmtp.cPassword = "Microsoft.09072019!" 

loSmtp.cSenderName= "wwIPstuff Samples"
loSmtp.cSenderEmail = MyEmail

loSmtp.cRecipient = MyEmail

*** Actual message properties
loSmtp.cSubject = "wwSMTP Test Message"
loSmtp.cMessage = "<b>HTML Test message from wwsmtp, to check out how this operation works.</b>"

*** If cMessage contains HTML set cContentType to text/html
loSmtp.cContentType = "text/html"

llResult = loSmtp.Sendmail()
IF llResult
    WAIT WINDOW "Mail sent..." nowait
ELSE
    ? "Mail sending failed: " 
    ? loSmtp.cErrorMsg
ENDIF

I get always the error:
"The SMTP server requires a secure connection or the client has not been authenticated. Server Response: 5.7.0 Authentication Required. Learn more at"

Please what is wrong?
Thank you very much for support

Hi Luca,

Could it be possible that you don't have access to the SMTP server "smtp.office365.com:587" ? Are you able to log in that SMTP server outside of wwsmtp ?

By the way, I read about your other post about wwDotNetBridge not working sometimes when sending email and working again afte server reset.

We have a very similar issue with wwsmtp where we get 'unknown member oBridge' in Function Createwwsmtp() when user tries to send email (from VFP 9.0 .exe application). Restarted the PC and it works again; then later it would fail, only sometimes. I'm going to try your Windows 8 compatibility mode solution and see if it works. Same as in your operation, our apps have been running for years and the error only happens to a small number of users and for those users only sometimes.

Steve Yu

Hi Steve,
I hope your problem is solved with the "Windows 8 compatibility" solution.
When I wrote this post i was trying to figure out if there was something wrong with sending emails for a particular account.
After several attempts, I realized that the error message "Authentication Required" is quite generic and masks the actual problem.
Later I realized that both Microsoft and Gmail have recently activated security procedures and this explains why the error appeared suddenly.
I finally solved the problem by following the Gmail 2-step activation and password app procedures.
In this way the error disappeared, the email sending routines were not responsible.
Of course, dealing with these paranoid issues is somewhat frustrating.