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Long-time user of "Google Apps for Your Domain".....what's the easiest way to migrate 10 family members to regular Gmail?

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I don't think there is a good option here because I don't think you can use the same domain. You would need to switch to a service that can have multiple mailboxes on a domain.

I can handle setting up new email that still uses the domain. The issue is all the data/purchases/etc with the Google Apps account that can't be transferred to a regular Gmail account.

Ah yes. That is also the problem I have and I don't think there is any option here. There was an internal experiment but I guess that didn't go anywhere before they decided to just close all of the accounts.

The wording sounds like non-"Workspace" services will still be available so i guess you can theoretically still access purchases. Not great, because now I have half of my stuff in different accounts but not too bad.

Add "Cloud Identity Free" to your subscription, seems to have let me keep all my purchases. (I canceled my legacy subscription today to avoid future charges)

It seems it's not possible to add "Cloud Identity Free Edition" to your account while the legacy subscription is still active, and I don't want to risk cancelling it before the deadline in case it has other unintended consequences :(

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