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I'm trying to restore a database backup made in SQL Server 2008 R2 to the 2014 Express version. Is this even possible? If I choose restore from device and select my backup file, I see no database in the drop down.

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Yes, you can, as long as the database is < 10 GB and doesn't use any features not supported by Express (you didn't mention what edition was being used in 2008 R2).

Stop using the broken point-and-click UI, and instead use a proper RESTORE DATABASE command:

RESTORE DATABASE DBFrom2008 FROM DISK = 'C:\backups\2008backup.bak'
  WITH REPLACE, RECOVERY,
  MOVE 'data_file_name' TO 'C:\...\database_name.mdf',
  MOVE 'log_file_name'  TO 'C:\...\database_name.ldf';

If you get errors from that (after replacing all of the obvious bits that are specific to your database and system), post those.

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Depends on what edition. What you're doing is basically a side-by-side upgrade. See full list of supported upgrade paths at https://technet.microsoft.com/en-us/library/ms143393(v=sql.120).aspx

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