SMTP Authentication Fail Error 530

Question

SMTP Authentication Fail Error 530

Jacob Jones 5

[✅] OAuth2 Token Retrieved Successfully!

[❌] SMTP Authentication Failed: (530, b'5.7.57 Client not authenticated to send mail.)

I have tried every thing I could think of but I don't know why I can't get SMTP to work.

Please help!

Jacob Jones 5

The python script that I used to test the SMTP auth

import requests
import smtplib

# Azure OAuth2 Credentials
CLIENT_ID = ""  #
CLIENT_SECRET = ""  
TENANT_ID = ""  
EMAIL_ADDRESS = ""  
SMTP_SERVER = "smtp.office365.com"
SMTP_PORT = 587

# Step 1: Get OAuth2 Token
TOKEN_URL = f"https://login.microsoftonline.com/{TENANT_ID}/oauth2/v2.0/token"
TOKEN_DATA = {
    "client_id": CLIENT_ID,
    "client_secret": CLIENT_SECRET,
    "scope": "https://graph.microsoft.com/.default",
    "grant_type": "client_credentials",
}

response = requests.post(TOKEN_URL, data=TOKEN_DATA)
token_json = response.json()

if "access_token" in token_json:
    ACCESS_TOKEN = token_json["access_token"]
    print("[✅] OAuth2 Token Retrieved Successfully!")
else:
    print("[❌] Failed to Retrieve OAuth2 Token:", token_json)
    exit(1)

# Step 2: Authenticate and Send Email via SMTP
try:
    server = smtplib.SMTP(SMTP_SERVER, SMTP_PORT)
    server.starttls()
    auth_string = f"user={EMAIL_ADDRESS}\x01auth=Bearer {ACCESS_TOKEN}\x01\x01"
    server.docmd("AUTH", "XOAUTH2 " + auth_string)

    
    recipient = ""  
    message = f"Subject: SMTP Test\n\nHello, this is a test email."
    server.sendmail(EMAIL_ADDRESS, recipient, message)
    print("[✅] Email Sent Successfully!")

    server.quit()
except Exception as e:
    print("[❌] SMTP Authentication Failed:", str(e))

Your answer

Jacob Jones 5 Reputation points

2025-02-27T10:25:14.6166667+00:00

The python script that I used to test the SMTP auth

import requests import smtplib # Azure OAuth2 Credentials CLIENT_ID = "" # CLIENT_SECRET = "" TENANT_ID = "" EMAIL_ADDRESS = "" SMTP_SERVER = "smtp.office365.com" SMTP_PORT = 587 # Step 1: Get OAuth2 Token TOKEN_URL = f"https://login.microsoftonline.com/{TENANT_ID}/oauth2/v2.0/token" TOKEN_DATA = { "client_id": CLIENT_ID, "client_secret": CLIENT_SECRET, "scope": "https://graph.microsoft.com/.default", "grant_type": "client_credentials", } response = requests.post(TOKEN_URL, data=TOKEN_DATA) token_json = response.json() if "access_token" in token_json: ACCESS_TOKEN = token_json["access_token"] print("[✅] OAuth2 Token Retrieved Successfully!") else: print("[❌] Failed to Retrieve OAuth2 Token:", token_json) exit(1) # Step 2: Authenticate and Send Email via SMTP try: server = smtplib.SMTP(SMTP_SERVER, SMTP_PORT) server.starttls() auth_string = f"user={EMAIL_ADDRESS}\x01auth=Bearer {ACCESS_TOKEN}\x01\x01" server.docmd("AUTH", "XOAUTH2 " + auth_string) recipient = "" message = f"Subject: SMTP Test\n\nHello, this is a test email." server.sendmail(EMAIL_ADDRESS, recipient, message) print("[✅] Email Sent Successfully!") server.quit() except Exception as e: print("[❌] SMTP Authentication Failed:", str(e))

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SMTP Authentication Fail Error 530

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