s 'Send Mail As' with Gmail - Fixing the Authentication Failed Error - Boshanka

‘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

20% Discount on your first year’s Google Apps Subscription!

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.

Drop me a line and I’ll send you a discount code you can use when signing up which will get you 20% off your first year!

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

 

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.

15 Responses to "‘Send Mail As’ with Gmail – Fixing the Authentication Failed Error"

  1. Chris Lewis  June 27, 2016 at 12:05 am

    Works like a charm! Thank you!

  2. John  September 9, 2016 at 1:57 am

    Thanks for this excellent tutorial – the best one on the web!!

  3. Ben  September 9, 2016 at 2:38 pm

    Thanks for the comment John! Glad you found the article useful!

  4. Audrey Howard  September 15, 2016 at 1:41 am

    Thanks so much – you’re a lifesaver!!

  5. emailevie  September 17, 2016 at 10:38 am

    YOU ARE AMAZING!!!! Thank you 🙂

  6. emailevie  September 17, 2016 at 10:46 am

    Do I need to set the sign in & security settings back in the admin console & My Account?

  7. Ben  September 17, 2016 at 12:56 pm

    Hey Evie, no you need to leave less secure apps set to on. If you turn that off it’ll stop working again. Goodness knows why google considers Gmail to be a ‘less secure app’!

  8. emailevie  September 17, 2016 at 8:20 pm

    Hi Ben, thanks for your reply, in the admin console I set it back to ‘Disable access to less secure apps for all users’ and now there is no option in MY Account to turn OFF ‘Allow less secure apps’. This should be ok anyway?

  9. Ben  September 19, 2016 at 10:20 am

    Hey Evie,

    That’s an interesting point, the first setting is you as an admin preventing users under your domain from accessing the setting which allows them to enable less secure apps to their accounts. It’s a security feature offered to admins to help protect their users.

    Logic would suggest that if you as the admin user turn it off, that not only will it remove the setting from your user’s accounts tabs, but it would also turn off the setting, effectively breaking any apps accounts set up in Gmail accounts.

    That being said i’ve not tested that exact scenario, so I’d be keen to know what happened when you tested it. But I’d put my money on it breaking things.

  10. Alex Straughan  September 22, 2016 at 5:17 am

    Hi there,

    I’m attempting to do the reverse of this, have Google Apps send from a Gmail address.

    While Less Secure Apps are enabled on the gmail account, sending emails bounces back with the following details:

    Google tried to deliver your message, but it was rejected by the relay smtp.gmail.com [IP]

    From what I can tell, looking into the Gmail Accounts security settings, SMTP.Gmail.com is blocking the IP address of the server that the Google Apps account is attempting to send from. As there are “Suspicious access blocked” logs occurring, coinciding with attempts to send emails.

    Any ideas on how to resolve this?

  11. Jason Draut  October 29, 2016 at 6:17 am

    It took me over an hour of fighting and looking google support before I found this page, then it took me 3 minutes to get it to work properly. Thanks!

  12. Ben  October 29, 2016 at 9:55 am

    @Jason that’s great to hear!

  13. Sahil Sethi  December 3, 2016 at 3:26 am

    Thank you thank you thank you! You saved me from a lot more frustration

  14. Enric Vives-Rubio  February 2, 2017 at 5:18 pm

    Thank you thank you thank you!!!! You save my life. But the best was your answer to a coment

    “Goodness knows why google considers Gmail to be a ‘less secure app’!”

    Jajajajajajaja!

  15. Ben  February 2, 2017 at 5:24 pm

    @Enric, Thanks for taking the time to comment! Glad you got it sorted 🙂

Leave a Reply

Enjoyed this article?

If you enjoyed this article please rate & share.

You Might Also Like