FIX: Gmail Message not delivered. You're sending this from a different address or alias using the 'Send mail as' feature (Solved)

Last updated on October 12th, 2020

The Gmail error message "Message not delivered. You're sending this from a different address or alias using the 'Send mail as' feature", means that you have incorrectly set up the additional email account you used to send the email.

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GMAIL allows you to send emails using a different email address that belongs to you (Send mail as). To take advantage of this feature, you need to add correctly the necessary settings for the email account you want to use (Username, Password and SMTP Server) to your Gmail account settings, otherwise you'll receive the following errors after sending an email:

  • "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 The settings for your 'Send mail as' account are misconfigured or out of date.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"
  • "Message not delivered.. You're sending this from another Google account using the 'Send mail as' feature. To send this message, please log in: https://accounts.google.com/signin/continue?s…The response from the remote server was:
    534 5.7.14 <https://accounts.google.com/signin/continue?s.."

Gmail Message not delivered. You're sending this from a different address or alias using the 'Send mail as' feature

How to fix the Gmail Error: Message not delivered. You're sending this from a different address or alias using the 'Send mail as' feature.

To solve the error "Message not delivered" in Gmail when using the "Send Mail As" feature, following the instructions below according your case.


Case A. Fix "Message Not Delivered" when using the "Send Mail As" feature with another Gmail account.

If you want to send an email from a secondary Gmail account you own, by using the "Send Mail As" feature in GMAIL, perform the following steps:

Step 1. Allow Less Secure Applications & Apps on the 2nd GMAIL Account.

1. Sign-In to your secondary Gmail account (the GMAIL account that you want to send mail as), and navigate to the following link:

2. Set the Access for less secure apps setting to: ON (Turn on).

gmail access for less secure apps


Step 2. Turn Off the 2-Step Verification on the 2nd GMAIL Account.

1. Sign-In to your secondary Gmail account, and navigate to Google My Account settings.

2. At "Sign-in & security" section, click Signing in to Google.

gmail 2 step verification

 

3. Set the 2-Step Verification option to Off. *

* Note: A pop-up window will appear to confirm that you want to turn off 2-Step Verification. Select OK.

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disable 2 step verification gmail


Step 3. Add the 2nd Gmail Account at your 1st Gmail Account's "Send mail as" settings .

1. Sign-In to your primary Gmail account and open GMAIL.

2. Click the Gear icon image on the top right and choose See All Settings.

3. Select the Accounts and import tab, and then click Add another email address on the 'Send mail as' options.

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4. At the first screen, type the Name and the secondary Gmail address that you want to use with the "Send mail as" feature (send email from) and click Next Step.

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5. At the next screen, click Send Verification to verify that you own this account.

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6. Sign-In to the secondary Gmail account your just added and open Gmail.
7. Open the new email message from the GMAIL team and follow the instructions on it to verify that you own the account you added.
8. When the verification is completed, you 're ready to use your additional google email address to send your emails.

TROUBLESHOOTING: If you still cannot add the additional Gmail Address with error: "Authentication failed. Please check your username/password and less secure apps access for…[GMAIL AGOOUNT]. Server returned an error: "535-5.7.8 Username and Password not accepted. Learn more at 535 5.7.8 https://support.google.com/mail/?p=BadCredentials…- gsmtp , code: 535", then re-enable the 2-Step Verification, generate an app password and use it to add the secondary email account in Gmail. The detailed instructions, can be found in this Google Help article.


Case B. Fix "Message Not Delivered" when using the "Send mail As" feature with a Non-Gmail Account.

If you want to send an email from an alternative email account you own (e.g. POP3, Office365, etc.), by using the "Send Mail As" feature in GMAIL, perform the following steps:

1. Sign-In to your Gmail account and open GMAIL.

2. Click the Gear icon image on the top right and choose See All Settings.

3. Select the Accounts and import tab, and then click Add another email address on the 'Send mail as' options.

Add another email alias gmail

4. At the first screen, type the Name and the alternative email address that you own and you want to use it with the "Send mail as" feature (send email from) and click Next Step.

Add Email Address to Send Mail As - Gmail

5. At the next screen, give the required information for the email address (account) you add:

  • Type the SMTP server name of the email account you are adding.
  • Type the Username of the email account you are adding.
  • Type the Password of the email account you are adding.
  • Specify the SMTP Server port and and the connection type.

6. When done, click Add Account and proceed to the next step (7).

TROUBLESHOOTING: If after clicking the "Add Account button" you receive one of the following errors, proceed as follows:

  • "Couldn't reach server. Please double-check the server and port number": At this case, ensure that you have specified the correct SMTP Server name, the SMTP Port number and the connection type.
  • "Authentication Failed. Please check your username/password": At this case, proceed and verify that the Username and the Password you specified to authenticate with the SMTP Server, are correct.
  • "Authentication failed. Please check your username/password. Server returned error: TLS Negotiation failed, the certificate doesn't match the host., code: 0": In this case, set the Port to 25, select the Unsecured connection and try again to add the account. *

* Note: If the "TLS Negotiation failed" problem persists, then you have to contact your email provider to correct the problem, as the error indicates that one of the following occurs:

    1. The SMTP Mail Server you specified, doesn't have a valid certificate or doesn't have a certificate at all.
    2. The certificate that the SMTP Mail Server provides to Gmail during the connection, doesn't contain the domain name, that Gmail uses to connect to the SMTP Mail Server.

Send mail through your SMTP Server

7. When you see the next screen:

1. Open the mailbox of the email account you just added and open the new email message from the GMAIL Team.

2. Click to open the confirmation link, or copy and paste the Confirmation code from the email message, to this window and click Verify.

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8. You 're done. Click the "From" line, in any message you compose to select the address to send from.

That’s it! Let me know if this guide has helped you by leaving your comment about your experience. Please like and share this guide to help others.

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