I'm sorry that you ran into trouble with this! Are you on OS X? It sounds like the Creative Cloud desktop application is unable to write to one of the files on your machine, and so the option is turned off. This usually only affects OS X machines, though.
If you are on OS X, run these steps to fix the problem:
1. quit the Creative Cloud desktop application
2. from the Go menu in the Finder, choose Go to Folder
3. paste in this path and click Go:
~/Library/Preferences/
4. In the window that opens, you should see a list of files including com.adobe.accmac.plist
5. click on com.adobe.accmac.plist and rename it com.adobe.accmac.plist.old. You'll be asked to confirm that you want to change the extension to .old.
6. start the Creative Cloud desktop application again.
If that doesn't help, or you are using Windows, please send us the recent log files from your computer at support@typekit.com and we'll look into it further:
help.typekit.com/customer/portal/articles/1649149#logs
Thank you,
— liz