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Outbound email server issues

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If you're getting errors and/or you're email is not sending out. Please follow the steps below to make sure you have TLS/SSL activated.

 

Configuring TLS/SSL for your email clients is crucial for securing your email communications, protecting your login credentials, and ensuring the privacy of your messages. TLS (Transport Layer Security) and its predecessor SSL (Secure Sockets Layer) encrypt the data exchanged between your email client and the mail server.

Most modern email clients automatically attempt to configure secure connections (TLS/SSL) when you set up a new account. However, if you're experiencing issues or want to verify your settings, here's how to manually configure TLS/SSL on Mac Mail, Outlook (Mac and Windows), and Thunderbird.

Before You Begin:

  • Consult Your Email Provider: The exact server names (incoming and outgoing), port numbers, and authentication methods can vary depending on your email provider. It's always best to check their support documentation for the most accurate settings. Common secure ports are:

    • IMAP (Incoming): 993 (with SSL/TLS)

    • POP3 (Incoming): 995 (with SSL/TLS)

    • SMTP (Outgoing): 465 (with SSL/TLS) or 587 (with STARTTLS)

  • Your Email Address and Password: Have these ready.

  • Server Hostname: This is usually something like mail.yourdomain.com or imap.yourprovider.com/smtp.yourprovider.com.


 

1. Mac Mail (Apple Mail)

 

For existing accounts:

  1. Open Mail.

  2. Click Mail in the top menu bar, then select Settings (or Preferences on older macOS versions).

  3. Click on the Accounts tab.

  4. Select the email account you want to configure from the left-hand pane.

  5. Click on the Server Settings tab.

  6. Uncheck "Automatically manage connection settings" for both Incoming Mail Server and Outgoing Mail Server (SMTP). This will allow you to manually adjust the settings.

  7. Incoming Mail Server (IMAP or POP):

    • Port:

      • For IMAP, typically change to 993.

      • For POP3, typically change to 995.

    • Use TLS/SSL: Ensure this checkbox is checked.

    • Authentication: Typically "Password" or "MD5 Challenge-Response."

  8. Outgoing Mail Server (SMTP):

    • Port: Typically 465 (for SSL/TLS) or 587 (for STARTTLS).

    • Use TLS/SSL: Ensure this checkbox is checked.

    • Authentication: Typically "Password" and ensure your full email address is used as the username.

  9. Click Save or OK to apply the changes.

  10. Close the Accounts window.

When adding a new account:

When you add a new account, Mail will attempt to automatically discover the settings. If it fails or you want to ensure secure settings from the start:

  1. Open Mail.

  2. Click Mail > Add Account...

  3. Select "Other Mail Account" and click Continue.

  4. Enter your Name, Email Address, and Password, then click Sign In.

  5. If Mail can't verify the account, it will prompt you to configure it manually.

  6. Select the Account Type (IMAP or POP).

  7. Enter the Incoming Mail Server (e.g., imap.yourdomain.com) and Outgoing Mail Server (e.g., smtp.yourdomain.com).

  8. Click Sign In.

  9. After the account is created, go to Mail > Settings > Accounts > Server Settings (as described above) to fine-tune the port numbers and ensure "Use TLS/SSL" is checked for both incoming and outgoing servers.


 

2. Microsoft Outlook

 

 

a. Outlook for Mac (2016 and newer)

 

  1. Open Outlook.

  2. Click Tools in the top menu bar, then select Accounts.

  3. Select the email account you want to configure from the left-hand pane.

  4. In the account settings window:

    • IMAP (Incoming) / POP (Incoming):

      • Ensure the Incoming server (e.g., imap.yourdomain.com or pop.yourdomain.com) is correct.

      • Port: For IMAP, typically 993. For POP3, typically 995.

      • Use SSL to connect (recommended): Ensure this checkbox is checked.

      • Username: Often your full email address.

      • Password: Your email password.

    • SMTP (Outgoing):

      • Ensure the Outgoing server (e.g., smtp.yourdomain.com) is correct.

      • Port: Typically 465 (for SSL/TLS) or 587 (for STARTTLS).

      • Use SSL to connect (recommended): Ensure this checkbox is checked.

      • Authentication: Often "Use Incoming Server Settings" or "Username and Password" (where you provide your email address and password again).

  5. Close the Accounts window. Outlook should automatically save the changes.

 

b. Outlook for Windows (2013 and newer)

 

  1. Open Outlook.

  2. Click File in the top-left corner.

  3. Click Account Settings, then Account Settings... from the dropdown menu.

  4. In the "E-mail" tab, select the email account you want to configure and click Change....

  5. In the "Change Account" window, note your Account Type (IMAP or POP3).

  6. Click More Settings...

  7. Go to the Advanced tab.

  8. Incoming Server (IMAP or POP3):

    • Port:

      • For IMAP, change to 993.

      • For POP3, change to 995.

    • Use the following type of encrypted connection: Select SSL/TLS (or simply "SSL" on older versions).

  9. Outgoing Server (SMTP):

    • Port:

      • For SSL/TLS, change to 465.

      • For STARTTLS, change to 587.

    • Use the following type of encrypted connection: Select SSL/TLS or STARTTLS (depending on your provider's recommendation). If 465, use SSL/TLS. If 587, use STARTTLS.

  10. Click the Outgoing Server tab.

    • Ensure "My outgoing server (SMTP) requires authentication" is checked.

    • Usually, "Use same settings as my incoming mail server" is sufficient, but your provider might require "Log on using" with your full email address and password.

  11. Click OK, then Next, and Finish. Outlook will test the settings.


 

3. Mozilla Thunderbird

 

  1. Open Thunderbird.

  2. Click the menu icon (three horizontal lines) in the top-right corner, then select Account Settings.

  3. Select the email account you want to configure from the left-hand pane.

For Incoming Server (IMAP or POP3):

  1. Click Server Settings under your account name.

  2. Server Type: (IMAP Mail Server or POP3 Mail Server)

  3. Server Name: (e.g., imap.yourdomain.com or pop.yourdomain.com)

  4. Port:

    • For IMAP, change to 993.

    • For POP3, change to 995.

  5. Connection Security: Select SSL/TLS.

  6. Authentication Method: Typically "Normal password" (the password itself is encrypted over the secure connection).

For Outgoing Server (SMTP):

  1. Click Outgoing Server (SMTP) at the bottom of the left-hand pane.

  2. Select the SMTP server associated with your account and click Edit...

  3. Server Name: (e.g., smtp.yourdomain.com)

  4. Port:

    • For SSL/TLS, change to 465.

    • For STARTTLS, change to 587.

  5. Connection Security: Select SSL/TLS or STARTTLS (depending on your provider's recommendation and the port you chose).

  6. Authentication Method: Typically "Normal password" and ensure your full email address is used as the User Name.

  7. Click OK to save the SMTP settings.

  8. Click OK again to close the Account Settings window.


Troubleshooting Tips:

  • Double-check everything: Even a single typo in the server name or port number can prevent the connection.

  • Firewall/Antivirus: Temporarily disable your firewall or antivirus software to see if they are interfering with the connection. If it works, you'll need to configure an exception for your email client.

  • Old TLS versions: If your email client or operating system is very old, it might not support the latest TLS versions (like TLS 1.2 or 1.3), which newer servers may require. Update your software if possible.

  • Provider-specific issues: Some email providers have unique setup instructions or require specific authentication methods. Always refer to their official documentation.

  • Test: After making changes, send a test email to yourself to ensure both sending and receiving are working correctly.

By following these steps, you should be able to successfully configure TLS/SSL on your Mac Mail, Outlook, and Thunderbird email clients, ensuring a secure and encrypted email experience.


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