We have had nothing but problems since the roll out of office 365.
We run a local mail server for our BT hosted domain up till march we had all our users set-up as alias names on our one domain based e-mail mail@domainname.co.uk our local server then collected this mail and fowarded to correct person.
This worked fine until march when alias accounts stopped working and e-mail rejected back to sender, replaced all alias names with real outlook accounts as name@domainname.co.uk and advised by BT got the accounts to all foward mail to main account and it was then working.
Have allways sent mail via smtp.btconnect.com which stopped working last week,
Now changed to smtp.outlook.com with correct ssl etc and all mail rejected as logon "btconnect" details do not match with @domainname.co.uk details. if i try to connect with user@domainname.co.uk then it fails to authenticate or states "550 5.7.1 Client does not have permissions to send as this sender."
We also have a fixed IP address with BT but cannot always send mail direct due to MX record/reverse DNS issues, I am therefore having to relay via gmail with forced reply address which then oftens fails spam checks.
Can anyone advise on settings that will work before we transfer everything to a host with working email facilities, on-line chat sent me a link to how to setup outlook!! and then said they could not give anymore advise