In order to properly configure maileater to connect to Office 365 Mail, please follow these steps:
1. We first need to obtain the proper SSL certificate for the Office 365 mail server.
Note1: As of Dec 2016, the Office 365 Certificate is signed by the "DigiCert Global Root CA". Information on this certificate can be found here. If outlook.com gets signed by a different root certificate in the future, you would need to obtain the new root certificate from Microsoft or find out what the root certificate is and grab it from the vendor.
Note2: If the Certificate file name has format <name>.txt, it should be renamed as <name>.cer
2. After gathering the information for your root certificate, create a file using Notepad with the certificate's information. For the example below, we are using the DigiCert Global Root CA which is valid for Office 365 as of Dec 2016:
3. Save the file and copy it to the primary server and make note of the path.
4. Use the following settings in the mailbox details screen (making sure to populate your full email address and file path to the certificate that you saved):
NOTE: Microsoft's recommended hostname/port values changed recently - Look at below link to obtain correct name/port numbers to be used, depending on the type of Outlook/Office365 account is being used:
Name: Default (or the name of your mailbox)
Check Interval (in Sec): recommended value is 30
Email Type: IMAP4
Hostname: outlook.com (This is NOT outlook.office365.com)
Port Override: 143 (It should be set to 143 and not the other ports like 993. This is because 143 is IMAP's STARTTLS port and maileater only supports STARTTLS)
User Name: The User ID of the Office365's account. (If it does not work, try and use the full email address)
Password: Fill in the password for the account
Security Level: Clear Text
Attachment Repository: Default is "Service Desk"
Attach Entire Email: Default is "No"
Force Attachment Splitout: Default is "No"
Allow Anonymous: Default is "Yes"
Save Unknown Emails: Default is "Yes"
Use Reply To Emails: Default is "Yes"
Use TLS: Yes
CA Certificate Path: Path to the Certificate file you just created.