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Microsoft Teams | Microsoft Teams Free | Chats
Text-based conversations between users with searchable history in Microsoft Teams Free
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Have you used this site to export your Skype chat history?
https://teams.live.com/dataexport/skype
If so, then you should know that data exported using this site do not cover any Skype chat history. The downloaded messages.json file contains only history of Skype Dial Pad phone calls. If you have not made any Skype Dial Pad calls within the last 30 days, then this .json file will be empty.
You can try to export Teams chat history:
https://teams.live.com/dataexport
This export file should contain both chats from Skype as well as the newer Teams chats. However, Microsoft has recently removed names of the older Skype contacts, so they will appear as "Unknown User", even though, the chat data should be still available.