What is the Problem?
Any emails I send to a free email address provided by Microsoft never arrive. This affects hotmail and Outlook.com.
Currently all my emails are being dropped by Hotmail/Outlook and the solution according to Microsoft is to add a SPF record to my DNS information.
Why is this happening?
Microsoft (Including hotmail and outlook) implement something called SenderID.
This checks to see if the email was sent from the correct domain and its matching IP address. It does this by checking the SPF record for the domain, which tells them where your emails are authorised to originate from.
You are either trying to send emails out via your own internet service providers mail servers, and claiming to be from your domain name, or your internet service provider is blocking you from accessing our mail servers, which normally results in the emails not sending at all.
What's the Solution
First, you should contact your internet provider to find out if "Outgoing mail relay" is disabled for your account. If it is, ask them to enable it for you. It can be done on an account level and takes only a few minutes. It's fairly typical for residential internet services to have this blocked but not for business internet connections.
If this is already enabled, then you should change your outgoing mailserver address to your own domain name, the incoming and outgoing mail servers we gave you when you signed up.
You can also check your SPF record and update it directly within cPanel "Email Deliverability > Manage" or ask us for help.
Once the spf record has been added to the dns record, and you are using your own mail servers, not your service providers, SenderID should stop blocking your emails.
Any other reasons for hotmail blocking emails?
Yes, its well known that hotmail have an over-aggressive anti-spam setup.
Microsofts anti-spam on its free email accounts (Hotmail and Outlook.com) is incredibly agressive and does not allow you to control it. Furthermore, emails get deleted without you ever knowing it had been sent to you.
So if you have performed all of the above and emails dont arrive, try sending the email in plain text, with no links nor attachments.