Cannot Send Gmail Mail App Mac

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Gmail seems to be the main email provider and no wonder – it is free and it has the best spam filtering and protection. But the Gmail web interface is a bit clunky so it is nice to be able to use Gmail with the built in Apple mail program. Here’s how to set up Apple mail to work with Gmail.

  • Several people are experiencing issues with Gmail (especially G Suite) email accounts in Mail on Mac. It seems that the Mail App is not working as expected for some Gmail users. More specifically, some Gmail users have said that after installing the macOS 10.14.4, and launching the Mail app, some Gmail users are asked to authenticate their.
  • 2017 iMac OS 10.13.6 Wife’s gmail went offline on Apple Mail. Mine works fine. I set up her own Gmail login with mail.google.com, checked iMap setting on, sent test email from my gmail, it all works. BUT I cannot get her gmail via Apple Mail to go online. Eventually removed her gmail from Apple mail, restarted, and attempted add gmail account.

1. Make sure you have a Gmail account.

Today I added my Gmail account to Mail. Mail is not registering any problems when I send from my Gmail account. Anything I send is placed in the 'sent' folder. When I log into Gmail any emails I send (from the Mail app) are present in the Gmail 'sent items' folder. HOWEVER, none of the emails are actually being sent.

You need to know your Gmail address (e.g. wayne@gmail.com) and password because you will need to enter them into Apple mail. If you don’t have a Gmail account here is how to sign up

– Go to gmail.com and click on “Sign Up”

– Fill in the details – you’ll need to pick a gmail email address and a password. After this is done you will get a verification page that says something like this at the bottom:

Can't Send Gmail On Mac

2. Enter your Gmail address into Apple mail.

– Open Apple mail, and go to the “Mail’ menubar at the top of the screen and then select ‘Preferences’ from the menu.

– Select the ‘Accounts’ tab. From here you can manage your mail accounts.

– Press the ‘+’ button – this means add a new account.

You will be asked which email provider – select Google.

-You will be prompted for your Google login details:.

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– You will be taken back to the Apple Mail preferences screen. There are some settings you should change here.

1. Click on the mailbox behaviours tab.

If there are problems in Apple mail with Gmail this is where they seem to be caused – multiple drafts appearing, deleted emails reappearing etc. It can take a bit of trial and error getting these settings right but these settings below have been working for me for over a year so this should give you a great head start. In these drop-down menus you will find a long list of folders. Some of them are folders in your Gmail account and some of them are folders on your home computer.

Here are the settings I suggest:

My recommended settings for mailbox behaviours when using Gmail in Apple mail. Junk is the Gmail junk folder. The only local folder is ‘Drafts’.

Notes on Mailbox Behaviours

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Select the local ‘On My Mac’ Drafts folder not the Gmail Drafts folder. This means that any drafts I begin to type on my home computer will not be available from my iOS devices. The other option is that you select the Gmail ‘Drafts’ folder. You should save draft messages on Gmail if you want your drafts to show when you open Gmail on the web. But the problem with this is Apple mail makes a backup copy of your draft email every few minutes as you are typing it. All these draft emails made by Apple mail will get stored in your gmail Drafts folder and you end up multiple versions of the same mail message.

You need to select the [Gmail] /Sent Mail folder because Gmail automatically keeps a copy of your sent messages and puts them in its ‘send mail folder.’ This tells Apple mail where to find those sent emails which is useful if you want to se your sent emails from different computers. You only need this option checked if your email provider doesn’t keep a copy of your sent emails automatically.

You don’t need to select a trash mailbox at all because Google automatically keeps a copy of your trashed mail. The “Trash” option is for email providers who don’t keep a copy of all your deleted emails. If you select a mailbox here Apple mail will save all your deleted items to this trash folder in case you want to undo the delete. This will result in multiple copies of all your trashed emails because Google already keeps a copy.

You want the Google “junk” option ticked not the local On My Mac one because Gmail automatically takes care of junk mail – you don’t want the Apple mail program deleting it. Don’t turn on the Apple junk mail filters. Gmail automatically sorts spam before it reaches your computer.

– That’s it.

– You can close the preferences window. (Click save if it prompts you to save the new settings).

– There should be some welcome messages from Gmail waiting for you in your Apple mail.

EXPLANATION OF GMAIL FOLDERS

On the left-hand side of your mail app there should be a little folder called [Gmail] that looks like this:

The All Mail folder contains every mail you have sent or received and even the emails you have deleted. This is where you go if you want to find an old email that you have deleted.

The drafts folder will be empty all the time because you are not storing your draft emails on the gmail server.

Sent mail will contain all the emails you have sent.

Trash will be empty. All your deleted emails are kept in the All Mail folder – you don’t need another copy in the trash.

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Kelly Heffner Wilkerson
February 26, 2018 at 10:00 AM
Categories: macOS | View Comments


Yesterday I helped a friend who had a problem where her outgoing email account (SMTP server) for a Gmail based email account kept appearing 'Offline' right after she set it up. Even adding the SMTP server manually in Mail didn't help.

You shouldn’t need to do any of the custom SMTP setup within Mail to get a Gmail based email account working in macOS. Now Gmail accounts should be setup just through 'Internet Accounts' in the System Preferences, and the SMTP will be setup automatically.

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Removing the account and setting it up again should take care of the issue.

If your SMTP server / Outgoing Mail Account constantly appears 'Offline', here's how to fix it:

  1. Close Mail if it's open now.

  2. Click the Apple menu (upper left corner of your screen) > System Preferences > Internet Accounts.

  3. Select the account with the broken outgoing mail server, and then click the minus sign at the bottom.

  4. Reboot your Mac.

  5. Click the Apple menu > System Preferences > Internet Accounts.

  6. Click Google, and sign into your Gmail based account again.

I Cannot Send Emails Out

Update February 26, 2018:

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If you're email is still not working after this, in Mail open the Mail menu > Preferences > Accounts and select your Gmail account. Ensure that the little checkbox for Enable this account is checked.