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Can not send email through GMAIL

I spent 2 hours and 14 minis on phone last night with a wonderful GoDaddy email person and neither he nor I were able to configure my GMail to "send" email via my domain. I have two email accounts that I need to do this with. we tried:




And, every configuration we could think of. My husband has his email set up this way and after the call we cross checked his settings to mine and they are the same as far as port, server, etc


Error Message received: 


Authentication failed. Please check your username/password.
Server returned error: "334 VXNlcm5hbWU6 334 UGFzc3dvcmQ6 535 5.7.3 Authentication unsuccessful [FRYP281CA0012.DEUP281.PROD.OUTLOOK.COM] , code: 535"


It is the correct password as I am able to go to Office 365 and login.


Is this a known issue - is there any additional assistance that I could get?  I realize that after 2+ hours and with GoDaddy help I am grasping at straws.


Thank you

Super User 2020



This is a common question and the short answer is I don't believe you will be able to accomplish this. The issue has to do with the authentication between Google and Microsoft and is not something GoDaddy can do anything about.


What I will also say is that while Office 365 has SMTP functionality - what you are trying to accomplish is NOT recommend as by just using the SMTP functionality you are bypassing / not using alot of the features that are built into Office 365 / Exchange server.


My suggestion is if you really want to use Google as your mail engine that you get a Google Suite (it has a new name) account instead of the Office 365 account. This is where you pay Google for mailboxes at your domain name powered by the Gmail service. It isn't a send as it is an actual mailbox / account

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