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I just upgraded the to Google Apps Unlimited from the free version of Gmail, the free version of Google Photos, and the free version of Google Drive.

I'd like to transfer all my settings, photos, and emails, along with future emails (my entire Gmail) to my new, paid account. All the documentation I've found is outdated or seems way to complicated for an app that I just paid for. Does Google have an app or documentation that I'm not seeing that covers this entire process of migrating and forwarding all of my old account's settings and assets?

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If you didn't find a good solution yet, for the Drive part - you can try Cloudsfer.com.

Cloudsfer is a web service for content migration between clouds and can migrate your files between the two Drive accounts

disclosure - I'm part of the Cloudsfer team

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From Migrate data between Google Apps accounts - Google Apps Help

Migrate data between Google Apps accounts

If you create a new Google Apps account for your organization, you can migrate your Gmail and Contacts data as well as information in Google Calendar, Drive, and Sites from your old Google Apps account to your new one. You can also migrate a personal Gmail account to your new Google Apps account.

Data transfer options are available for the following types of data:

See follow the above link see the details for each item the the following list:

  • Email
  • Contacts
  • Calendars
  • Drive files
  • Sites
  • Other Google Apps
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