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One of the issues that can spoil your day is being unable to send emails. Just imagine the frustration of having your most important communication sitting in your outbox. We have seen many Mac users grappling with this issue, especially after upgrading to the Mojave. Some have complained that their Mail app in Mojave can receive email but can’t send; every time they send an email, it ends up in their outbox. In this post, we will help you troubleshoot the email issue in Mojave and hopefully get your Mail app working again.

There is a close correlation between this problem your iCloud account. But typically the issue is in the form of an SMTP server connection error. The first thing that the Mail app does before sending a mail is to perform a DNS search for the IP address of the receiving email server. So, if the search is successful, the app will send your email credentials to that mail server to confirm that you have a valid account there. After that, it will establish a TCP connection. If any of the processes fails, your email won’t be sent.

Here are other common causes of the problem:

• Network connection errors
• Bad passwords
• Email ports and ISP blocks
• SSL connection problems

Now that you know the culprits, it is time to fix the issue.

What to Do If You Can Receive but Cannot Send Email Using Mail App?

If your Mail app in Mojave can receive emails, but it can’t send them through the outgoing mail server, try these tricks:

• Check if the outgoing mail server (SMTP) is set as specified by your email service provider. Most SMTP servers require valid login information for it to send emails. So, if your outgoing mail server settings are inaccurate, you may experience difficulties while sending emails.
• Establish if there are restrictions placed upon your accounts. Sometimes the administrators of your Mac may have activated parental controls for your usage of the app, which means you have to request permission to send emails.
• If the above tricks don’t work, consider checking your connection in the Mail Connection Doctor. It will reveal more information about the problem. To launch this utility, go to Windows and select Connection Doctor. Sometimes, your firewall software may block email traffic on ports 25, 465 or 587. Other times, your systems could be affected by another firewall, such as a firewall software built into an internet sharing router. In such instances, the best thing to do is to contact the relevant party for information.

Check If Your Email Provider Is the Problem

If the Mail app says that your account is offline, the first thing to check is your network. If your Mac is connected and you still can’t send email using the Mail app in Mojave, the problem could be your email provider, which could be experiencing a service outage. To resolve the issue, you can visit their websites to check system status. For instance, if you are using iCloud Mail, Apple’s system status page will show the status of this service.

Sometimes, your email service provider may only allow you to send emails under stricter settings. In such a case, you can contact your provider, and then adjust your outgoing mail settings to your preferences.

Rectifying Missing or Outdated Settings

Outdated or missing settings in the Accounts option of Mail Preferences could be the culprit. If that is the case, your account will appear to be offline even when you are connected to the internet. To rectify this anomaly, launch Mail and select the Preferences option from the Mail menu, then click Accounts and choose your email account. You can get the mail settings from your provider or use the Mail Settings Lookup tool to view your settings. After that, compare these settings with what you have in your Mail Preferences.

SMTP Authentication

As mentioned earlier, the Mail app issue is closely linked to incorrect SMTP authentication settings. The best way to rectify the problem is to re-authenticate and provide the outgoing server with the right password and login information. Here is how to do it:

• Launch the Mail App.
• Go to the Mail menu and choose Preferences.
• Highlight the Accounts tab from the Preferences window.
• Choose the affected email account and choose the Account Information tab, then tap on the Outgoing Mail Server (SMTP) option.
• From here, select Edit SMTP Server List.
• Under Edit SMTP Server List, choose the Advanced tab.
• Now re-enter your password and login credentials for the problematic email account on this section.
• After that, hit OK and close the Preferences If prompted, select Save to confirm the changes.
• Your Mail app should now work as usual. To confirm if it works, try sending a new email to yourself or a friend.

If the test email goes through, you shouldn’t worry about the unsent messages in your outbox because the app will re-send them.

Check SSL Connection Settings

As a security measure, most email service providers now require that you connect to SMTP via a secure connection. For this reason, you should send your emails through SMTPS since it uses SSL to secure connection between the server and your email client.

Likewise, some servers may also force you to connect on port 465, instead of port 25. But if both port 465 and port 25 fail, try port 587.

Scan for and Clean Junk on Your System

Sometimes there could be a bug in the Mail app that causes email accounts to lose or modify outgoing mail server (SMTP) information. Unless you are a tech-savvy, manually removing such a bug can be a bit advanced. For this reason, you need a robust Mac repair toolkit to help you remove junk on your Mac.

On top of this, ensure that you have installed the latest MacOS updates, especially if the issue occurred after upgrading to the Mojave.

That’s it. We hope this troubleshooting guide was helpful to you. Please let us know how it goes in the comments.

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.

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).

Mail App On Mac Wont Authenticate Iphone

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

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.

Xbox One Authenticate Mac Address

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

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

Mail App On Mac Wont Authenticated

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.

Mail App On Mac Wont Authenticate Windows 10

See also: macOS Mojave Draining Your Mac Battery Life? Here Is How To Fix