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Q: When Microsoft in its infinite indifference decided to abandon Skype (which I often used) and tell the faithful to shift to its Teams, it promised that the address book would automatically transition.

 Well, it didn’t. My son in Colorado didn’t have any problems but neither of us could figure out where dear old dad went amiss.

 My only guess is that it wants me to upgrade my MS 365 Family to something more expensive. My current Family subscription doesn’t expire until next September.

 – Doug B.
Niceville, Florida

A:  Ah, yes.  A true “Thanks, Bill!” moment.  It was supposed to be a seamless digital handshake. You click a button, the gears of the Microsoft cloud grind for a moment, and your decades-long rolodex of Skype contacts migrates effortlessly into Microsoft Teams. Instead, you’re staring at an empty “People” tab, wondering where your great-aunt’s video link and your freelance designer’s contact card disappeared to.

If it feels like your address book vanished into the ether, don’t panic. As of December 2025, we are navigating the final sunset of the consumer Skype era, which is a shame, because I for one, liked Skype, and there is a lot about Teams that I could do without. Nevertheless, while Microsoft officially retired the classic Skype brand in May 2025, they’ve left the lights on—just barely—until June 2026 for data recovery, and, yes, transfer of contacts to Teams.  If you are experiencing a failed transfer, it’s probably not a “broken” button; rather, it’s a synchronization mismatch. Let’s see what we can do ti get those contacts moving.

The most common reason for a failed migration is an identity mismatch. Back in the day, Skype users created “Skype Names” (like TechWizard82). Later, Microsoft forced everyone to link those to a Microsoft Account (an email).  If you are logging into Teams with an email address, but your Skype contacts are tied to an old, “unlinked” Skype Name, Teams won’t see them. To fix this, try signing out of Teams and signing back in using your original Skype Name as the username. If the migration prompt finally appears, you’ve found the culprit.

For reasons known only to the software engineers in Redmond, the standard version of Teams sometimes “forgets” to trigger the migration script. A reliable workaround in 2025 is to join the Teams Insider Program.  Think of this as getting the “beta” version of the app. It often includes more robust syncing tools that the stable release lacks. Click the three dots (…) by your profile picture in Teams, head to Settings, and look for the Teams Insider program tab. Join, restart the app, and you may find that the “Sync Skype Contacts” prompt miraculously appears on the next launch.

If neither of these automated methods work for you, there is a fully manual path that you can take that will bypass any “Transfer” buttons entirely.  It’s a fairy simple “Export, then Import” operation.

Head over to the Skype Data Export Portal at TinyURL.com/IGTM-0962. You’ll need to be logged-in, of course.  Check the box for “Contacts” and hit “Submit Request.” Within a few minutes, you’ll receive a download link for a Comma-Separated Values, or .csv file.  This file format is not specific to any platform or software, and can be used in situations like this to exchange data across apps.

Once you have the .csv file, you might think that the next step is to head over to Teams.  You would be mistaken.  Teams is notoriously picky about directly importing .csv files – and that’s okay. The cleanest way to handle this is to import that file into your Outlook Contacts, using the same Microsoft account. Once the contacts are in Outlook, they will automatically populate the “People” section of Teams. 

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 Well, my dear readers, this brings a close to the 19^th year of It’s Geek To Me.  I fear that 2026 may see the end of this experiment, as the quantity of questions has slowed to almost nothing.  If you’re not ready to see it end, you can do your part by heading over to the column’s website and feeding it a question or two.  Remember, I answer questions on all aspects of technology – not just computers and Windows.  In the meantime, I wish you all a very happy and prosperous New Year! 

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