Make sure your mail app isn't set to check for new email too frequently. Try signing in directly on the Gmail app. When I authenticate using the Outlook I chose to use Kerberos Authentication not domain. Outlook 2011 for Mac uses the virtual directory of EWS. You may have to experiment with either 3DES or AES-128 depending on the certificate. The email client's sign-in method might be insecure. Port: 465 with SSL or Port: 587 with TLS Require Authentication: Yes. On my user accounts, I chose authentication using AES-256 Kerberos because it matched my certificate on my server. If the tips above didn't help, visit and follow the steps on the page. 
If you recently changed your Gmail password, you might need to re-enter your Gmail account information or completely repeat your Gmail account setup on your other email client. Allow less secure apps: If you don't use 2-Step Verification, you might need to allow less secure apps to access your account. Important: If you sign in with OAuth, use your regular Google password. In the Port field, enter one of the following numbers: If youre using SSL, enter 465. Remember anyway that if you use a normal SMTP server like the ones that come with your Gmail or Hotmail account. On your device or in the app, enter as the server address. IMAP and SMTP ports should be set to standard plain text IMAP and SMTP ports. These extensions work by enabling encryption on plain text service ports. STARTTLS extensions are enabled by selecting use of them in 'Secure IMAP (TLS)' or 'Secure SMTP (TLS)' selection menu. The first reason is that your outgoing mail server (SMTP) doesn't allow to send emails without user authentication and the other reason is that your email address is marked at spam lists as a source of spam. Secure SMTP servers use tcp 465 port by default. Solution 1: Patient's email address is invalid. The server responses was: 5.1.0 Address rejected. The server response was: you must authenticate first (5.5.1). No wonder that the iPad has become one of the most used tool to send emails on-the-go: its practicality and its beautiful design make it an excellent device for emailing. The 'Server Error: Relay Access Denied 554 5.7.1' in Outlook occurs for two main reasons. The server response was: 5.1.0 Authentication required. Use an App Password: If you use 2-Step Verification, try signing in with an App Password. To make your iPad mail client work and correctly deliver your emails, you need to configure its SMTP settings. Then when you reconnect, accept the Cert., and re-authenticate (you may have to temporarily disable password-saves until you are re-prompted). OUTLOOK FOR MAC 5.1.0 AUTHENTICATION REQUIRED PORT COMCAST 465 UPDATE
Update your email client to the latest version.If you have these problems or can’t sign in, first check to make sure you’re using the right password.
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