I am getting an SSL verification failed error when trying to send emails with the Sendgrid web api. I'm not even sure what cert it is trying to verify here. I have done all of the user and domain verification on my Sendgrid account and I am using very straightforward sending process. Here the error urllib.error.URLError: <urlopen error [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1000)>  Heres the code mailClient = SendGridAPIClient(os.environ.get('sendGridKey')) message = Mail( from_email=os.environ['sendGridEmail'], to_emails="dev@cribbi.co", subject="User Message for %s" %newMessage['chatId'], html_content = "<strong>" + newMessage['message']['text'] + "</strong>" ) mailRes = mailClient.send(message) 
Here is a link to the answer. It is not sendgrid specific but Python version specific. I was able to use the link provided in this answer to find the script that I needed to run to update the SSL certs for python. urllib and "SSL: CERTIFICATE_VERIFY_FAILED" Error