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‘Send Mail As’ with Gmail – Fixing the Authentication Failed Error

‘Send Mail As’ with Gmail – Fixing the Authentication Failed Error

Below you’ll learn how to fix the Gmail Server error which appears when adding a Google Apps 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 Apps, and have tried to set up your Google Apps 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) ]

Authentication Failed. Server response: 534-5.7.14 Error

Authentication Failed. Server response: 534-5.7.14 Error

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”

Step 1.

Sign into http://apps.google.com with your Google Apps Administrator domain, username and password.

Sign in to your Google Apps Administrator Account

Sign in to your Google Apps Administrator Account

 

 

Enter your Google Apps Administrator Username and Password

Enter your Google Apps Administrator Username and Password

 

Step 2.

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.

Google Apps - Security in the Admin Panel

Click Security from the admin panel or Search using the box at the top

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I mentioned earlier that I use Google Apps, the google dedicated suite of business class tools is essential, and it starts with good email. For what you get it’s an inexpensive solution that will save you time and money in the long run.

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Get Started with Google Apps

 

Step 3.

Click to expand the ‘Basic Settings’ Section

Open Basic Settings in The Security Panel

Open Basic Settings in The Security Panel

 

Step 4.

Click the “Go to settings for less secure apps ››” link next to Less Secure Apps

Click the Less Secure Apps Link

Click the Less Secure Apps Link

 

Step 5.

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.

Ensure ‘Allow users to manage their access to less secure apps’ is set

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!

Step 6.

Next we need to access the ‘My Account’ page for the Google Apps user you’re trying to add to your personal gmail account. So if you’re trying to add ‘ben@mydomain.com’ to ben@gmail.com, you need to be signed into ben@mydomain.com. This may well be your Google Apps 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/.

Access My Account from the top right, or sign in via https://myaccount.google.com/

Access My Account from the top right, or sign in via https://myaccount.google.com/

 

Step 7.

From the My Account dashboard of your Google Apps user account, click the ‘Sign In & Security’ link.

Click the 'Sign In & Security' link.

Click the ‘Sign In & Security’ link.

 

Step 8.

From the left hand menu on the Sign In and Security Page, click ‘Connected Apps & Sites’

Click 'Connected Apps & Sites'

Click ‘Connected Apps & Sites’

 

Step 9.

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’

Check Allow Less Secure Apps to ON

Check Allow Less Secure Apps to ON

 

Step 10.

Log out of your Google Apps 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’.

Gmail - Add another address that you own

Gmail – Add another address that you own

 

Step 11.

In the pop up window that appears, enter your name and the email address, then click on ‘Next Step’.

Add another email address that you own

Add another email address that you own

 

Step 12.

In the next window, enter ‘smtp.gmail.com’ as the SMTP server. Then enter the email address and password of the google apps user account you’re trying to add. Then press ‘Add Account’.

Enter your google apps user account info

Enter your google apps user account info

 

Step 13.

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 Apps 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.

Gmail - Confirm verification and email address.

Gmail – Confirm verification and email address.

 

Step by step video tutorial.

Below you’ll find a full video which takes you through the entire process of adding a Google Apps email address to a personal Gmail account.

Want More Freelance Advice?

Need further advice for boosting your freelance career? My blog at Boshanka features regular guides and tips for aspiring freelancers. Just visit boshanka.co.uk/freelance-advice or follow me on social media to stay updated on all the latest posts.

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