Usage of Teams once, breaks ability to use Skype
Dear Admins, please get on the same page as your design teams and support staff, they’re giving users contradicting information.
I just had a conversation with Microsoft Support about the ability for a Skype user to talk to a Teams user…basically at this time there is no such thing as interoperability despite their documentation regarding coexistence modes.
The very minute a user even tries Teams just once…they break the ability to use Skype to talk to you if you’re using Teams. Apparently it’s been in this broken state for months and is “by design.”
Here’s the quote from the rep, “Teams is designed to only send messages to Skype for Business if the recipient has NEVER used Teams. Once the recipient like USER B has signed into Teams (even just once), all messages from other Teams user like USER A, would ONLY be sent to Teams.”
The support rep even admitted Microsoft’s documentation does not match this current broken system. There is no actual migration path from Skype to Teams, there is no actual interoperability. If you have a 1,000 users and just one tried out Teams then you have to decide either everyone uses Skype or everyone uses Teams, nothing in between.
It’s crazy but the truth is you can safely disregard everything in this article: docs.microsoft.com/en-us/microsoftteams/tea..
I’m desperately trying to keep Slack at bay in my organization, but this just gives Slack users more ammunition.
Microsoft, please get it together and provide us true interoperability that matches up with your documentation.

5 comments
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Matt commented
This has recently been changed somewhat I think? Seems to be more a case of if User A initiates a conversation from Teams to User B using Teams and then logs out of Teams, the private chat window becomes disabled (showing User A that User B is no longer active in Teams) though can restart another private chat which will then allow their message to be sent to the user via SFB.
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Charles Chang commented
We are facing the same issue. We either have to roll back Teams completely or move everybody to Teams ASAP. The one thing holding us back has been the audio/video call requirement for screen sharing.
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John Barnes commented
In the article, "Migration and interoperability guidance for organizations using Teams together with Skype for Business," Microsoft explains exactly what you just described. In the "Detailed mode descriptions" section, Islands mode reads, "A single user runs both Skype for Business and Teams side-by-side. This user receives chats initiated in Teams by another user in: 1.) Skype for Business, provided the recipient is homed online and never logged in to Team, and 2.) Teams in all other cases.
Skype/Teams interop to functions as designed, so long as the person using Skype never logs into Teams; If they do, there's no turning back.
Link to the article: https://docs.microsoft.com/en-us/MicrosoftTeams/migration-interop-guidance-for-teams-with-skype
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Nathan Berger commented
The information on this suggestion is now outdated. "Islands" and "Sfb Only" are the only available upgrade configurations at the moment.
If I recall correctly, the update got pushed out for a Coexistence setting, but was not kept due to an error that occurred. Coexistence is supposed to be here soon, based on MS documentation from July.
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Anonymous commented
A person having both Teams and Skype installed on the machine but, has logged out of Teams and currently using Skype application.
Other users of Teams can not get messages from such a person.
This support should be provided because many of the new Teams users may face familiarity issue and would prefer to stick with Skype in peak working hours.