How to Solve Hotmail Deliverability Problems with Salesforce
Outlook.com's spam filter, which includes hotmail.com and live.com, is sometimes a little bit too smart. Legitimate emails can easily end up in the spam filter. Even the popular site StackOverflow had problems with this.
Figuring out what happens is difficult because the email sometimes doesn't even end up in the junk folder. It vanishes in the void.
If you want to be confident that your email will be delivered, you should use a well respected mail provider like SendGrid or Mailgun to take care of this.
SMTP Relay is middleware between Salesforce and your outgoing email server and can be used to greatly improve email deliverability and reliability.
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