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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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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.

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43 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’!”


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

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

  16. estulin  February 9, 2017 at 8:12 pm

    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?

  17. Pizza  March 29, 2017 at 5:30 am

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

  18. Orion  April 20, 2017 at 2:35 am

    Thank you very much!

  19. Dave  May 11, 2017 at 4:13 pm

    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!



  20. alercunha  June 1, 2017 at 10:35 pm

    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.

  21. Ben  June 9, 2017 at 11:04 am

    Hi Dave,

    Thanks for the really kind comment – I’m so glad you got it working! Thanks also for pointing out the Two Factor Authentication issue – sounds like that’s a bit of a curveball in the whole process!


  22. pearlsandvodkablog  August 29, 2017 at 8:00 pm

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

  23. Ben  August 29, 2017 at 10:36 pm

    Hi Pearls, You don’t need to repeat step 6 for every account, as that’s at the google apps admin overview level – but you will need to repeat steps 7 onwards for each gsuite account you wish to access via gmail SMTP.

  24. Rajesh Prajapati  September 19, 2017 at 5:13 pm

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

  25. Web Dev  October 12, 2017 at 3:21 pm

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

  26. Yaron  October 24, 2017 at 11:58 am

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

  27. Gavin  November 5, 2017 at 9:40 am

    Yes, yes, yes!. Thank you.

  28. Jan  December 5, 2017 at 3:36 am

    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? 😉

  29. Ben  December 5, 2017 at 8:22 am

    Haha thanks, im so pleased the article helped! Of course, share away 🙂

  30. Rich  March 9, 2018 at 5:23 pm

    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?

  31. Rich  March 9, 2018 at 5:31 pm

    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.

  32. Albert Tseng  March 22, 2018 at 4:43 pm

    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?

  33. Albert  March 22, 2018 at 7:14 pm

    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!

  34. Ben  March 23, 2018 at 9:53 am

    @Albert – Well done buddy, I didn’t know about the propagation delay – so thanks so much for posting back with your solution! I’m going to update the article with this info!

  35. Gemma  April 14, 2018 at 11:06 pm

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

  36. Rebekah J Disch  May 16, 2018 at 7:22 pm

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

  37. Aaron Dahl  June 5, 2018 at 1:39 am

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

  38. Muffi Zainu  June 25, 2018 at 10:47 am

    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.

  39. Ben  June 27, 2018 at 5:07 pm

    Hey Muffi, I already Added Albert’s comments to the article, they’re at the end of step 5 🙂

  40. Yvette  August 14, 2018 at 9:13 pm

    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”.

  41. Kat Bern  August 30, 2018 at 11:37 am

    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!

  42. Dave Hansen  August 30, 2018 at 9:20 pm

    Brilliant! Thank you.

  43. sarahannfelton  November 8, 2018 at 3:39 pm

    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.

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