Problem

When trying to communicate with external Skype people our Skype for Business Office 365 users were getting the message “This message wasn’t sent to … due to company policy”

Skype - This message wasn't sent to ... due to company policy

When we tried to add an external contact we would get the message “..or it is outside your organization and is not federated with your company..”

or it is outside your organization and is not federated with your company

Cause

My External Sharing rules for Skype in the admin center underĀ Settings => Services & add-ins => Skype for Business were set to allow external sharing.

skype_external_01

The clue was in the message “not federated with your company”. I went back to basics and used the Check DNS option under Settings =>Domains to verify configuration on the DNS for the domain. I found there was issues with the service locator SRV records for Skype.

skype_external_03-copy

Resolution

Skype requires two SRV records on the name server for the domain and without them external communication will not work as expected.

For my SRV records the target was correct but my domain name was appended to the the end of the target. The strange thing was when I looked at the configuration on the name server for this domain the settings seemed fine. For this domain my name server was daily.co.uk

skype_external_04

In the end it turned out I was missing a period (.) at the end of the targets. Daily.co.uk and maybe some others will append the domain name to the end if you don’t add a period after the .com making the values invalid and Skype external communications fail.

skype_external_07