‘Send Mail As’ with Gmail – Fixing the Authentication Failed Error (UPDATED March 2021)

Bish
Bash
Boshanka
Let's get it done!

Fix the Gmail authentication error.

0 Shares

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) ]

Authentication Failed. Server response: 534-5.7.14 Error
  • Save
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 https://workspace.google.com/ with your Google Workspace Administrator domain, username and password.

Sign in to your Google Apps Administrator Account
  • Save
Sign in to your Google Workspace Administrator Account
Enter your Google Apps Administrator Username and Password
  • Save
Enter your Google Workspace 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
  • Save
Click Security from the admin panel or Search using the box at the top

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

I mentioned earlier that I use Google Workspace, 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 Workspace

Step 3.

Click to expand the ‘Basic Settings’ Section

Open Basic Settings in The Security Panel
  • Save
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
  • Save
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.

  • Save
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 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/.

Access My Account from the top right, or sign in via https://myaccount.google.com/
  • Save
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 Workspace user account, click the ‘Sign In & Security’ link.

Click the 'Sign In & Security' link.
  • Save
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'
  • Save
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
  • Save
Check Allow Less Secure Apps to ON

Step 10.

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’.

Gmail - Add another address that you own
  • Save
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
  • Save
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 Workspace user account you’re trying to add. Then press ‘Add Account’.

Enter your google apps user account info
  • Save
Enter your google Workspace 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 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.

Gmail - Confirm verification and email address.
  • Save
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 Workspace 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.

5 2 votes
Article Rating
Subscribe
Notify of
guest
53 Comments
Oldest
Newest Most Voted
Inline Feedbacks
View all comments
Chris Lewis
4 years ago

Works like a charm! Thank you!

John
4 years ago

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

Audrey Howard
4 years ago

Thanks so much – you’re a lifesaver!!

emailevie
emailevie
4 years ago

YOU ARE AMAZING!!!! Thank you 🙂

emailevie
emailevie
4 years ago

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

emailevie
emailevie
4 years ago

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?

Alex Straughan
4 years ago

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?

Jason Draut
Jason Draut
4 years ago

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!

Sahil Sethi
4 years ago

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

Enric Vives-Rubio
Enric Vives-Rubio
4 years ago

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!

estulin
estulin
4 years ago

Works great but now I can’t use 2-step verification I get the following message.

Message not delivered
You’re sending this from a different address or alias using the ‘Send mail as’ feature. The settings for your ‘Send mail as’ account are misconfigured or out of date. Check those settings and try resending.

Is there a workaround?

Pizza
Pizza
4 years ago

But why… gmail is saying gmail is less secure??

Orion
Orion
3 years ago

Thank you very much!

Dave
Dave
3 years ago

Ben, thank you VERY much!

You’re a life saver. What was interesting for me, is that it worked initially without your steps – but then it stopped after one day and the only way to get things straight again was following your instructions.

The one area that I ran into was in Step 9 the key that needed to be selected to change it to blue was not there. I thought it might have something to do with I had two-factor generation turned on. I generated a two-factor password and used that in Step 13 and now everything is fine.

It is unclear to me why two-factor might have that 3rd box on screen 9 so it does not show up, but I did not want to go back and turn off two-factor at this now that it is working (again).

Your post extremely well written and very much appreciated!

Thanks,

–Dave

alercunha
3 years ago

Took me a long time to find the solution, thank you very much for posting this. It’s really undocumented issue that is hard to get right unless you know where to look. Thanks again.

pearlsandvodkablog
3 years ago

Do I need to do this on all the accounts that I’m adding to my gsuite?

Rajesh Prajapati
Rajesh Prajapati
3 years ago

I Use my office mail (which is not google app) send as through gmail free version. What is the work around for that?

Web Dev
Web Dev
3 years ago

Thanks! I was looking for this solution for months now!

Yaron
Yaron
3 years ago

Perfect, thanks a lot!
My organization is already 2 weeks with email problems!

Gavin
Gavin
3 years ago

Yes, yes, yes!. Thank you.

Jan
Jan
3 years ago

You, Sir, are a genius! After about an hour on phone with google rep and ticket escalations (to no avail), I am so lucky to have found your instructions. Mind if I share this with Google along with my case id? 😉

Rich
Rich
3 years ago

I’m not sure what’s different, but I’m hitting a problem in Step 9. The section titled “Allow Less Secure Apps” isn’t there…I’ve triple-checked the first 8 steps and everything looks good. Thoughts on what could be different?

Rich
Rich
3 years ago

Of course, right after leaving this comment, I think I figured it out. The account I was setting up had two-factor authentication turned on. Turning it off made the missing section show up. It appears that turning two-factor off, then setting up the ability to send emails from my gmail account, and then re-enabling two-factor got me back to the place I wanted to be. In the future, if I hit problems, I’ll try generating a password for the gmail account to use to login.

Albert Tseng
Albert Tseng
3 years ago

Hi there… i just tried these instructions, but unfortunately it didn’t work. I was able to add two Gsuite alias email addresses a few weeks ago and messages were sending out fine, but then one day last week it stopped letting me send from those addresses (error message). I deteled the aliases and then tried to re-add but then getting that authentication error still after following the directions.

Any suggestions?

Albert
Albert
3 years ago

solved! – after talking with the G-suite help desk, they discovered from Tier3 support that changing the setting to “Allow users to manage their access to less secure apps“ takes some time before propagating to all the accounts (sometimes 4 to 6 hours). “Enforce” can take 24 hours. So, I tried it again, and it finally worked. all set. thanks!

Gemma
Gemma
3 years ago

AMAZZZZINNNNG! I was losing it over here trying to work out what was going wrong and this worked like a charm. 🙂 Thanks!

Rebekah J Disch
2 years ago

Thank you SO much for this. I was pulling my hair out trying to figure out how to resolve this issue. Lifesaver!

Aaron Dahl
2 years ago

Thanks for the post. I was pulling my hair out trying to determine why this was not working.Cheers!

Muffi Zainu
2 years ago

Thank you!
Request to add Albert’s comments (March 22, 2018 at 7:14 pm) about 2 step verification to the main text. Because that’s the same issue I faced.

Yvette
Yvette
2 years ago

Thank you so much for this step-by-step picture guide!

It’s super easy to follow and helped me figure out a workaround for trying to add more than the limit of 5 emails under the “Check mail from other accounts”.

Kat Bern
2 years ago

Hi Ben,

thanks for this tutorial.

I have done everything you specified, double-checked everything, waited for things that may be delayed to have time to make the desired changes and EVERYTHING, I mean everything that you’re talking about here step by step looks the same, yet I still get the error.

Do you know if there is any other reason/problem that could cause this error? Note one difference in what I’m trying to do is that I’m adding my @gmail to @mydomain, not the other way round.

Can you think of anything else I should be doing?

Thanks in advance!
Kat

Dave Hansen
Dave Hansen
2 years ago

Brilliant! Thank you.

sarahannfelton
sarahannfelton
2 years ago

Any suggestions for someone without GSuite? I am using Google Domains and they have email forwarding options that dont require GSuite. In addition to this, there are instructions on how to set up the send email as option but they are giving me the same error listed above. I have the less secured apps allowed on my settings and thats all i can change. There isnt an email/security option in the admin console.

Ian S
Ian S
1 year ago

REALLY helpfull tutorial, thanks. This problem was driving me nuts. Don’t understand why Google calls its own Gmail program a “less secure app”!

Malc
1 year ago

This post just keeps on giving – Thanks.

For anyone still wondering why google seems to classify their own gmail app as “less secure” – it’s to do with OAuth – which is a token based authorisation system.
Basically Google is classifying any app (including POP and IMAP ) that requires you to enter your password as ‘less secure’ because it could be hacked, or intercepted etc. .
With Oauth you generate a one time token and pass that to the app. The token is only valid for the requesting app and so it doesn’t matter if someone else gets hold of it – they won’t be able to access your mail with it – that makes it ‘more secure’ 🙂

Yeongha Kim
1 year ago

Thank you so much!

Costin
Costin
1 year ago

this does not help at all if you do not have gsuit account…any help for this?

Davidson J Ospina
Davidson J Ospina
27 days ago

Worked perfectly! Thank you very much.

Sanket Patole
Sanket Patole
27 days ago

thank you

ackeber
8 days ago

No comment. Just very grateful for that. Thanks

Phew.
You've made it this far.

I am good at managing my schedule, so I can usually get projects booked in without much lead time. Let’s get our heads together and get your project done.

Get a Quote
Bish
Bash
Boshanka
Let's get it done!

Based in London, Working Everywhere

I’m a Freelance Web Designer and WordPress developer, I’m based in London but work with client’s in the UK and all over the world.

Creative Web Design & WordPress Development Services

Contact Me