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Mar 27, 2019 Users say they end up bouncing between macOS and Google sign-in pages in Safari. Screenshot via Apple Support Forum User WesleydeSouza. One user says the issue “puts me in an endless loop. I get a notification ‘Google requires completing authentication in Safari.’” The user is then taken to a sign in dialog where he enters his login info.
Apple on Monday released macOS 10.14.4 to the public. The new Mac operating system provides new features such as automatic Dark Mode in Safari, Apple News+ and more. Unfortunately, the update seems to be causing some users to be unable to authenticate their Gmail accounts in the Apple Mail Account.
A growing number of users on the Apple Support Forums are complaining that macOS 10.14.4 breaks the ability for the Mail app to authenticate their Gmail account. Users say they end up bouncing between macOS and Google sign-in pages in Safari.
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One user says the issue “puts me in an endless loop. I get a notification ‘Google requires completing authentication in Safari.’” The user is then taken to a sign in dialog where he enters his login info. The password is accepted, but he then is taken back into the loop, where he is asked again to enter his Google password.
The sign-in issue appears to be limited to the Apple Mail app. Other apps that use Google information, such as Calendar, don’t seem to be affected.
Users report attempting to fix the issue by removing and re-adding accounts, changing passwords, removing two-step, and more, none of which resolve the issue.
The issue appears to affect both new and existing Mail accounts on macOS. Once a user has installed macOS 10.14.4 and has rebooted, they are prompted to authenticate their Google account, placing them in the dreaded authentication loop.
So far, it isn’t know whether or not the bug affects every mac 10.14.4 user, or just a particular group of users. The full Apple Support thread is available here.
Add your email account
If you don't have an email account set up, Mail prompts you to add your email account.
To add another account, choose Mail > Add Account from the menu bar in Mail. Or choose Apple menu > System Preferences, click Internet Accounts, then click the type of account to add.
- When adding an account, if you get a message that your account provider requires completing authentication in Safari, click Open Safari and follow the sign-in instructions in the Safari window.
- If necessary, Mail might ask you for additional settings.
Learn more about how to add or remove email accounts.
Send and reply
Mail App In Mac Google Requires Completing Authentication In Safari Park
Learn how to compose, reply to, and forward email.
Send new messages
- Click New Message in the Mail toolbar, or choose File > New Message.
- Enter a name, email address, or group name in the 'To' field. Mail gives suggestions based on your contacts and messages on your Mac and devices signed into iCloud.1
- Enter a subject for your message.
- Write your email in the body of the message.
- To add an attachment, drag an attachment to the body of the message. Or choose File > Attach Files, choose an attachment, then click Choose.
- To change your font and format, use the options at the top of the message window.
- Beginning with macOS Mojave, it's even easier to add emoji to your messages. Just click the Emoji & Symbols button in the toolbar at the top of the message window, then choose emoji or other symbols from the character viewer.
- Send or save your message:
- To send, click the Send button or choose Message > Send.
- To save your message as a draft for later, close the message, then click Save.
Reply and forward
To reply to a single person, click Reply , type your response, then click Send .
To reply to everyone on a group email, click Reply All , type your response, then click Send .
- To forward a message to other people, click Forward , type your response, then click Send .
Organize and search
Sort your emails into folders and use multiple search options to find specific messages.
You can create Mailboxes to organize your emails into folders.
- Open Mail, then choose Mailbox > New Mailbox from the menu bar.
- In the dialog that appears, choose the location for the Mailbox.
- Choose your email service (like iCloud) to access your Mailbox on your other devices, such as an iPhone signed into the same email account.
- Choose On My Mac to access your Mailbox only on your Mac.
- Name the mailbox and click OK.
If you don't see the mailboxes sidebar, choose View > Show Mailbox List. To show or hide mailboxes from an email account, move your pointer over a section in the sidebar and click Show or Hide.
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Sort your emails
To move a message from your Inbox to a mailbox:
- Drag the message onto a mailbox in the sidebar.
- In macOS Mojave, you can select the message, then click Move in the Mail toolbar to file the message into the suggested mailbox. Mail makes mailbox suggestions based on where you've filed similar messages in the past, so suggestions get better the more you file your messages.
To delete a message, select a message, then press the Delete key.
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To automatically move messages to specific mailboxes, use rules.
Use the Search field in the Mail window to search by sender, subject, attachments, and more. To narrow your search, choose an option from the menu that appears as you type.
Add and mark up attachments
Attach documents and files to your messages and use Markup to annotate, add your signature, and more.
Attach a file
To attach a file to your message:
- Drag an attachment to the body of the message.
- Choose File > Attach Files, choose an attachment, then click Choose.
Use Markup with your attachments
You can use Markup to draw and type directly on an attachment, like an image or PDF document.2
- Click the Attach button or choose File > Attach Files in the message window.
- Choose an attachment, then click Choose File.
- Click the menu icon that appears in the upper-right corner of the attachment, then choose Markup.
- Use the Sketch tool to create freehand drawings.
- Use the Shapes tool to add shapes like rectangles, ovals, lines, and arrows.
- Use the Zoom tool in the Shapes menu to magnify and call attention to a part of an attachment.
- Use the Text tool to add text.
- Use the Sign tool to add your signature.
- Click Done.
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- Contact Apple Support.
1. All devices signed into iCloud with the same Apple ID share contacts. Contacts addressed in previous messages that were sent and received on those devices are also included. To control this feature, turn Contacts on or off for iCloud. On Mac, choose Apple menu > System Preferences, then click iCloud. On iOS devices, go to Settings, tap your name at the top of the screen, then tap iCloud.
2. Markup is available in OS X Yosemite and later.