When Microsoft started offering 60 free Skype minutes per month to Office 365 subscribers, they allowed the minutes to be linked either a standalone Skype account created before Microsoft acquired Skype, or a Skype account linked to Microsoft (a.k.a. live.com) account.
Microsoft has decided that they are only going to allow free Skype minutes to be linked to the Skype account associated with the same account as your Office 365 subscription. They rolled out this change on March 1, 2017, without any prior notice to affected users, by disconnecting the free Skype minutes subscriptions. Users received a misleading email notification that their subscription had “expired” with no explanation of the actual reason for the change:
Neither Microsoft nor Skype support personnel were notified that this change was coming or trained in how to respond to users who contacted them about it.
I corresponded with Skype support personnel for months trying to get a straight answer about why my subscription was disconnected from my Skype account and how to reconnect it. When they started completely ignoring my emails, I escalated by sending a letter via certified-mail to the president of Microsoft.
In response to my letter, an “escalated support request” was created on my behalf. I was then told:
I understand that you would like to connect the Skype Minutes associated to your Office 365 subscription to a specific Skype profile.
Unfortunately, this is no longer an option, the Office 365 Skype Minutes are now required to be associated to the same account that the Office 365 subscription is associated to. This is why you have been unable to attach the Skype Minutes to the Skype profile [elided].
In order to use the Office 365 Skype Minutes on the account [elided] you would need to combine this Skype profile with your Microsoft Account with the Office 365 subscription. You can combine the accounts by signing into the Skype profile on https://login.live.com/ and following the on screen instructions to combine the accounts.
Alas, these instructions don’t work either. I had to explain this to the support person who was helping me four times over the course of ten days before he finally listened to what I was saying. On June 15, he finally responded:
I wanted to thank you for the screenshot of the message you receive when you attempted to link your Skype profile to your Microsoft Account. I am currently researching this issue and will send you an update as soon as I have one.
Then, on June 21:
I am working with our back office group for both Office and Skype to come up with a resolution to the issue, but do not have any new information for you at this time. As soon as I have more information or an estimated timeframe for a resolution to be available I will immediately send you an update.
Then, on June 27:
This issue is appearing to be more widespread than we initially anticipated, causing more than just your account to not be able to choose the Skype profile associated to the Office 365 Skype Minutes. As soon as we have a resolution for this issue, I will immediately contact you.
In case it isn’t obvious, the reason why this is a problem is because people need to keep their old Skype username — which they’ve given out for years — and they have contacts, subscriptions, etc., associated with their old Skype account, so they can’t just throw away their old account and switch to the account associated with their Office 365 login.
The fact that Microsoft failed to anticipate this issue and address it proactively — informing affected customers, training support personnel, having a tested, working mechanism in place for people to combine their Skype profile with their Microsoft account — is concerning, to say the least. It’s hard to believe that Microsoft would screw up this badly if it considered Skype an important part of its product line.