Why are WordPress emails being blocked by Outlook, especially for the same domain?

Email marketer from WP Mail SMTP shares that if the 'From' email address in your WordPress settings is a free email address (like Gmail or Yahoo), Outlook may be more likely to block the email. Using an email address associated with your domain can improve deliverability.

Email marketer from MailPoet recommends checking your email logs for any error messages or clues about why emails are being blocked. Many SMTP plugins provide logging features that can help you diagnose the problem. Also, test different email subjects and content to see if specific words or phrases are triggering spam filters.

Email marketer from Reddit says the key is to use a proper SMTP service for sending WordPress emails. Hotmail/Outlook are very strict and if your emails aren't properly authenticated, they will be blocked. Using a plugin to relay emails through a service like SendGrid or Mailgun will fix this.

Email marketer from Email Geeks suggests using an SMTP plugin with an external SMTP relay, suspecting the web host IP reputation might be the issue.

Email marketer from DigitalOcean Community mentions that shared hosting environments often have poor IP reputations due to other users' actions. Outlook may be blocking emails based on the IP address of the hosting server. Switching to a dedicated IP or using a transactional email service with a good reputation can help.

Email marketer from Email Geeks suggests running a message trace in M365 if the Outlook recipient is an M365 mailbox.

Email marketer from StackOverflow says that if you're sending emails from a WordPress site on the same domain as your Outlook email, you might be running into a loop or conflict. Outlook might see the email as coming from itself and block it. Try sending from a different domain or subdomain.

Email marketer from Namecheap says to ensure that your domain's DNS records are configured correctly. Incorrect MX records, missing SPF records, or misconfigured DKIM settings can lead to email deliverability issues with Outlook. Double-check these settings with your hosting provider and email service.

Email marketer from WPBeginner suggests that WordPress emails often end up in spam because they aren't properly authenticated. The default WordPress email function uses the `wp_mail()` function, which doesn't always include the necessary headers for proper authentication. Using an SMTP plugin to connect to a dedicated email sending service can resolve this.

Email marketer from Kinsta explains that some security plugins can interfere with WordPress's ability to send emails. If you're using a security plugin, try temporarily disabling it to see if it's causing the issue. Also, check the plugin's settings for any email-related configurations.

Email marketer from A2 Hosting notes that Outlook has strict spam filtering. Certain words or phrases in your email's content or subject line could be triggering spam filters. Experiment with different content to see if that improves deliverability.

Expert from Email Geeks explains the issue may stem from using a Godaddy-purchased O365 instance, which has extra security measures, and suggests contacting Godaddy for assistance with custom settings.

Expert from Spam Resource explains that your domain's reputation is critical for deliverability. If your domain has been associated with spam in the past or has poor sending practices, Outlook is more likely to block your emails.

Expert from Spam Resource explains that sending to old and unengaged addresses increases your chances of bounces and spam complaints, damaging your sender reputation. Cleaning your list regularly helps improve deliverability.

Expert from Email Geeks asks if the emails are being properly authenticated.

Expert from Email Geeks suggests the problem sounds like an authentication issue or a security setting issue in O365.

Expert from Word to the Wise explains that missing or misconfigured SPF and DKIM records are common reasons for deliverability problems. Make sure these authentication methods are properly set up to verify your email's legitimacy.

Documentation from RFC Editor (Request for Comments) explains that having a valid Reverse DNS (rDNS) record for your mail server can help improve email deliverability. An rDNS record maps an IP address to a domain name, and it's used to verify that the mail server is legitimate.

Documentation from EasyWP SMTP Plugin explains that a Sender Policy Framework (SPF) record is crucial. It specifies which mail servers are authorized to send emails on behalf of your domain. If the WordPress server isn't listed in the SPF record, Outlook may flag emails as suspicious, especially if the 'From' address uses the same domain as the recipient's Outlook address.

Documentation from Microsoft explains that Outlook.com uses filtering technologies that might block legitimate email. Factors include sender IP reputation, domain reputation, content, and authentication. Sending from a domain that also has Outlook.com mailboxes can create internal confusion and filtering issues if not properly configured.

Documentation from Postmark explains that a DomainKeys Identified Mail (DKIM) record adds a digital signature to outgoing emails. This signature verifies that the email hasn't been tampered with during transit and confirms the sender's identity. Missing or misconfigured DKIM records can cause Outlook to treat emails as spam.