‘Send Mail As’ with Gmail – Fixing the Authentication Failed Error (UPDATED March 2021)
Filed in Tutorials & Resources
Fix the Gmail authentication error.
Below you’ll learn how to fix the Gmail Server error which appears when adding a Google Workspace account inside of a personal Gmail account. Full tutorial is below along with a step by step video at the end of the post.
If you’re using Google Workspace , and have tried to set up your Google Workspace email account inside of a second personal Gmail account, you may have run into an error similar to this one:
Here’s the error:
Authentication failed. Please check your username/password. [Server response: 534-5.7.14 <https://accounts.google.com/ContinueSignIn?sarp=1&scc=1&plt=AKgnsbsLl 534-5.7.14 seEmTxE-R3JVrc5VFcU9AxKbnIfoFDtYiaGcgpQqClrUmVwF9qfwh_SFwJD6bWOFj03NDU 534-5.7.14 SJzyq9bOjjGSV2wXXYBYPzZAH8uZnIutOn1EpK-VykSyTqV91lBe61y55kPS4mQC5UdCsO 534-5.7.14 ufPMl3GhO__OVIYC5jUYvIxN1ppDBLGnq1sWtX5-zy5DpqsT6Jsk0N8B_HYEPN_q5e372y 534-5.7.14 YApDJIVv7yCRxOBTKIRh0ICptzWk> Please log in via your web browser and 534-5.7.14 then try again. 534-5.7.14 Learn more at 534 5.7.14 https://support.google.com/mail/answer/78754 87sm4925917lft.20 – gsmtp code(534) ]
Support for this issue is poorly documented by google, and like many before, you’ve probably been pulling your hair out trying to find a solution.
Fear not. There is an answer!
How to fix the “Gmail Authentication failed. Please check your username/password” Error. Also known as the “Server response: 534-5.7.14 Error”
Sign into https://workspace.google.com/ with your Google Workspace Administrator domain, username and password.
Once you’re in. Click ‘Security’. If you can’t see it, type Security into the search field at the top of the Admin Console.
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Click to expand the ‘Basic Settings’ Section
Click the “Go to settings for less secure apps ››” link next to Less Secure Apps‘
If it’s not set already. change the setting on this page to “Allow users to manage their access to less secure apps“. If this is already set, don’t worry, there’s another change we need to make before everything will start to work :-). Once you’re done. Press ‘SAVE‘ in the bottom right.
Please Note – 4 – 6 Hour Propagation Delay
After changing the setting “Allow users to manage their access to less secure apps”, there can occasionally be a period of 4 – 6 hours before the setting takes effect on all of your accounts. With “Enforce” taking up to 24 hours. Thanks to Albert Tseng for the heads up about this!
Next we need to access the ‘My Account’ page for the Google Workspace user you’re trying to add to your personal gmail account. So if you’re trying to add ‘[email protected]’ to [email protected], you need to be signed into [email protected] This may well be your Google Workspace Administrator account too, In which case, you’re already signed in.
If it is the same account, and you’re already signed in, you can access the my account page by clicking the icon in the top right hand corner of the screen you’re on, then clicking the blue ‘My Account’ button. If it’s a different account, you simply need to sign in via https://myaccount.google.com/.
From the My Account dashboard of your Google Workspace user account, click the ‘Sign In & Security’ link.
From the left hand menu on the Sign In and Security Page, click ‘Connected Apps & Sites’
Scroll down on the Connected Apps and Sites section and in the last box you’ll see the title ‘Allow less secure apps: on/off’ – press the switch to the right to make it go blue. So the title Reads ‘Allow Less Secure Apps: ON’
Log out of your Google Workspace user account and visit www.gmail.com. Enter your personal gmail username and password to login. Once you’re in, press the cog in the top right hand corner. Then click on the ‘Accounts and Import’ tab. Inside the ‘Send Mail As’ section click on ‘Add another email address that you own’.
In the pop up window that appears, enter your name and the email address, then click on ‘Next Step’.
In the next window, enter ‘smtp.gmail.com’ as the SMTP server. Then enter the email address and password of the google Workspace user account you’re trying to add. Then press ‘Add Account’.
On the next screen, if the account has been successfully added you’ll be asked to enter a verification code. This code will have been emailed to the Google Workspace user email account you’ve just added. Log in to that account and grab the code, then enter it in the box. Or alternatively, click the link included in the email to verify your account. And that’s it. Job done 🙂 Make yourself a brew.
Step by step video tutorial.
Below you’ll find a full video which takes you through the entire process of adding a Google Workspace email address to a personal Gmail account.
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