File "C:\Users\SanketPatil\AppData\Local\Programs\Python\Python38\lib\smtplib.py", line 655, in auth raise SMTPAuthenticationError(code, resp) smtplib.SMTPAuthenticationError: (535, b'5.7.139 Authentication unsuccessful, the request did not meet the criteria to be authenticated successfully. Contact your administrator. [PN2PR01CA0009.INDPRD01.PROD.OUTLOOK.COM]')

Process finished with exit code 1

I have enabled SMTP auth too

CodePudding user response：

Issue is related to some security enablement's or opening of ports related. You may try the below steps and try accessing. If it is working, then it can be confirmed related to default security and enable the required security features and re enable the security defaults.

• Firstly login into to Azure portal
• Click on Azure Active Directory
• Then click onProperties.
• Then Click on Manage security defaults.
• Now make Enable security defaults =No.
• Now click on Save button

References: