Adding Emails

Question

I am trying to add emails but when I do it denies them and does not send them to people with emails like icloud.com and gmail.com.

Answer 1

Hi Marley Brathwaite

I understand you're able to send emails, but messages to domains like Gmail and iCloud are being rejected.

Have you already tried the Q&A Assist suggestions? To help me guide you correctly, could you please confirm:

• What type of account are you using? (Outlook.com / Gmail / iCloud / ISP email / custom domain)
• Do you see any error message or code when sending? (e.g., “550 relay denied”, “5.7.1 rejected”)
• Does sending to non-Gmail/iCloud addresses work normally?

In the meantime, please try the following:

1, Check if your email address matches the sending account

Sometimes Outlook allows sending from an address that doesn’t match the authenticated account, which external providers reject.

• Go to “File” > “Account Settings” > “Account Settings”
• Double‑click your account
• Make sure “Email Address” matches your actual mailbox login

2, Test sending from Outlook Web

This helps confirm if the issue is with Outlook app or the account itself.

• Sign in to Outlook on the web via a browser
• Send a test email to a Gmail address
• If it works, issue is in Outlook app configuration
• If it fails, account/provider-side restriction

3, Check if your account is being flagged for spam protection

Some providers silently block outgoing emails to major domains if the account sends too many messages or looks suspicious. Try to:

• Send a simple email with no links or attachments
• Use a short subject + plain text

4, Re-add the account in Outlook (quick reset)

If settings look correct but still fail:

• Go to “File” > “Account Settings” > “Account Settings”
• Remove your account
• Add it again using “Add Account”

Note: If you're using POP, emails stored locally may not sync back, please confirm before removing.

Please feel free to let me know how it goes after trying these steps. Thank you for your time and understanding.

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Answer 2

The most likely cause is that the outgoing (SMTP) server is rejecting messages as “relaying” when sending to domains such as icloud.com and gmail.com. This happens when the SMTP server does not recognize the sender as an authorized user.

To fix this in Outlook for Windows (classic):

1. Open the account settings
   • In Outlook, go to File > Account Settings > Account Settings.
   • Select the email account and choose Change.
2. Verify outgoing server (SMTP) settings
   • Confirm the Outgoing mail server (SMTP) name and port match the values provided by the email provider or ISP.
   • Select More Settings….
   • On the Outgoing Server tab, select My outgoing server (SMTP) requires authentication.
   • Choose Use same settings as my incoming mail server.
3. Check encryption and port
   • On the Advanced tab, verify the SMTP port and encryption type (SSL/TLS or none) match the provider’s documented settings.
   • If unsure, contact the email provider/ISP for the correct SMTP port and security settings.
4. Test sending
   • After saving changes, send a test email to an icloud.com or gmail.com address.
   • If errors still occur, capture the exact error text (for example, 550 or 553 relay denied) and provide it to the email provider or admin for further diagnosis.

If the account is an iCloud mailbox being used on a Windows 8/RT Mail app or Windows Phone 8 (older devices), ensure the documented iCloud IMAP/SMTP settings are used (imap.mail.me.com on port 993 with SSL for incoming, smtp.mail.me.com on port 25 without SSL and with authentication for outgoing) as incorrect settings can also cause send failures.

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References:

• I receive a 550, 553, or relay-prohibited error when sending email messages
• You experience issues when you add Kerio or iCloud email accounts