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When you migrate to Office 365, the preferred configuration is to have user email addresses and UPNs the same. Having a single identity makes it easier for users to understand. If you are implementing Skype for Business in Office 365, it will take the UPN of the user as the Skype address. Again, keeping a single identity is good. However, if you have an on-premises implementation of Skype for Business, then the Skype identity is configured in the attribute msRTCSIP-PrimaryUserAddress .  This attribute contains a SIP (session initiation protocol) address that looks like an email address but with “sip:” at the start. For example: “sip: user @contoso.com”. The SIP addresses defined in your on-premises Skype for Business may or may not match the email addresses of the users. You need to verify whether the addresses match. If the SIP address does not match the email address, it is easy to change. On the Skype Server run the following PowerShell command: Set-CsUser -Identity userUPN -SipAdd

Note : Most of my blog posts are technical items that relate to performing a specific task or fixing a specific error. This one is more of an opinion piece. So, if my arguments sound reasonable, take the advice. If you disagree, by all means, go your own way. I am a big believer that I need to understand the details of any script I run in a production environment. Unless that script is from Microsoft and provided to perform a specific task (such as migrating public folders), I will go through a script line by line to verify I understand it. This even applies to my own scripts. If I haven’t used a script for several months, I’ll review it before I use it again to make sure I know exactly what it’s doing. I expect that most system administrators operate with the same requirement to understand the scripts they are running. At least I hope they do. I don’t want anyone blindly running a script I created without understanding the script and knowing what it will do in their environment. So, f