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Jan 03, 2018 If your SMTP server / Outgoing Mail Account constantly appears 'Offline', here's how to fix it: Close Mail if it's open now. Click the Apple menu (upper left corner of your screen) System Preferences Internet Accounts. Select the account with the broken outgoing mail server, and then click the minus sign at the bottom. Reboot your Mac. Click the Apple menu System Preferences Internet Accounts. Click Google, and sign into your Gmail based account again. I have always used the Apple Mail client on my Mac for several email accounts. Lately since upgrading to MacOS 10.14.4 Mojave, my Gmail account keeps going offline. I have isolated this to the outgoing SMTP server. Closing and restarting Mail fixes the problem but not permanently. Gmail goes offline usually within a few hours. My Gmail account in Mac mail errors multiple times a day 'Login Failed', clicking it initiates re-login and it works for a bit. All my software is up to date, I have two step authentication turned on, Gmail is iMap, the account has been deleted and added numerous times.

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 email addresses. They get a notification saying:

See also: macOS Mojave Freezes or Stops Responding, Fix

“Enter the password for the account “(null)”: Google requires completing authentication in Safari.” This takes users to a Google web login form. However, shortly after authenticating, the Mail app asks for authentication once again, and again, as the process does not stick and goes into an endless loop.

Please note that we contacted Apple regarding this issue, and we were told that Apple is currently working on a fix.

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In the meantime, you can try the following fixes:

1– Changing your Gmail account’s security settings may fix this problem. Open Google’s My Account site (https://myaccount.google.com) and click Security (On the left navigation panel) and then scroll down and find the “Less secure app access” section and turn this on (note that Google recommends this OFF).

See also: Mail App Keeps Crashing

2- Set up your email account using IMAP. Please note that this process will delete your messages and will no longer available on your Mac. But do not worry, your mails will not be removed from Google’s servers, you can still access your mails via gmail.com web site. Here is how:

  • Open the Mail App
  • Click Mail
  • Click Preferences
  • Click Accounts
  • Select your Gmail account
  • And click the (-) remove button
  • Now we will re-add your Gmail account
  • Before that, let us make sure that IMAP access is enable. If not, you can do that easily. To enable IMAP in Gmail, login into your Gmail web client (gmail.com) and then click Settings:
  • Click the Forwarding and POP/IMAP tab
  • Select Enable IMAP (IMAP access section)
  • And scroll down and click Save.
  • Now again in Mail App, choose Mail
  • Click Add Account
  • Select Google, then click Continue
  • Enter your email and click Next
  • Enter your password and click Next
  • And follow the instructions

If this does not work, try the “Add Other Account” option and add smpt/imap info manually:

  • Incoming server: imap.gmail.com
  • Outgoing server: smtp.gmail.com

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3- Open Safari and go to https://accounts.google.com/b/0/DisplayUnlockCaptcha and then enter your username and password, then enter the letters (captcha) then try again.

4-Please try the following:

  1. Quit Mail App.
  2. Open Keychain (Applications > Utilities or Spotlight Keychain)
  3. Search: google.oa
  4. Find the accounts that you are having trouble accessing, and delete Keychains
  5. Now go to https://accounts.google.com
  6. Sign in with your problematic account
  7. Click Security (left menu)
  8. Find the “Third-party apps with account access” section and click “manage third-party access”
  9. Click macOS and to revoke its access
  10. Then sign out (https://accounts.google.com)
  11. On your Mac, go to System Preferences > Internet accounts and re-authenticate your account
  12. And open your Mail and try again

5-Still having the problem? if so try this:

  1. Download and install Charles (a proxy app): https://www.charlesproxy.com/latest-release/download.do
  2. Authorize automatic proxy, when asked
  3. In Charles go to the Help menu and then choose SSL Proxying > Install Charles Root Certificate
  4. Keychain Access will open. Find the “Charles Proxy…” (you may type Charles to search).
  5. Double click on it.
  6. Expand the Trust section and set to “Always Trust”.
  7. Close the window, enter your password when you are asked.
  8. In Charles, choose SSL Proxying Settings (Proxy menu).
  9. Add a new location with Host: people.googleapis.com
  10. Go to the Tools menu and then choose Rewrite and click Add.
  11. Add a new location with Host: people.googleapis.com.
  12. Add a new action:

Type: Body

Where: Response

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Replace Value: {“names”:[{“metadata”:{“primary”:true},”displayName”:”Your Name”}],”emailAddresses”:[{“value”:”your@email”}]}

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  1. And now on your Mac, open System Settings and Internet Accounts and re-authorize your account.
  2. Now test to see if it is working, if your issue is resolved now, feel free to remove the Charles app.
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See also: macOS Mojave Draining Your Mac Battery Life? Here Is How To Fix

So make an effort to keep your inbox relatively clear by filing incoming messages as soon as possible.Check Mail Less FrequentlyMail always slows down a bit when checking messages, so if you set it to do so less often, it will feel faster. Best speed up software for mac. The inbox is especially sensitive to large numbers of messages, and more so with IMAP accounts than with POP ones. If your Previous Recipients list gets too long, addressing can get pretty poky. If you have a mailbox with more than 1,000 or so messages, consider splitting it into two or more smaller mailboxes. Choose Mail: Preferences, click on the General button in the toolbar, and choose a less frequent schedule from the Check For New Mail pop-up menu (see “Patience, Patience”).Check Previous RecipientsMail maintains a list of everyone to whom you’ve sent a message, and it consults this list when you address new messages.