Trying to restore 2008 backup to 2016 I backed up a 2008 R2 database and copied to a server with a 2016 SQL Server. I tried using the restore database dialog but it does not seem to want to work. When I use the dialog I have the following:



The drop down for Database is empty. Also when I grabbed that sibk file the open dialog was looking for *.bak, *.tm and *.log and the backup created in 2008 is none of those. So I chose All Files. Not sure that's a clue to the problem.
The fact that he database drop-down is blank suggests to me that the backup file is invalid/corrupt in some way.

First, try and restore the backup file header to confirm that the file is a valid SQL backup. In Management Studio, connect to your SQL 2016 instance and open a new query window. Run the following:

RESTORE HEADERONLY FROM DISK = 'C:\Users\nasscribe\Documents\sibk\sibk'


If you receive an error from this query, either it is not a valid SQL backup file (possible that there was a write error during the backup process on your 2008 R2 instance, or you just grabbed the wrong file), or it is a permissions issue where the SQL Service account cannot access the file, and you'll see something similar to below:


  Msg 5120, Level 16, State 101, Line 1 Unable to open the physical file
  "C:\Users\nasscribe\Documents\sibk\sibk". Operating system error
  5: "5(Access is denied.)".


If you receive the above message, copy the backup file to somewhere like C:\Temp\ and retry.

If instead you see an error like this:


  Msg 3241, Level 16, State 0, Line 3 The media family on device
  'C:\Users\nasscribe\Documents\sibk\sibk' is incorrectly formed. SQL Server cannot process
  this media family. 
  
  Msg 3013, Level 16, State 1, Line 3 RESTORE
  HEADERONLY is terminating abnormally.


Then the backup file is not a valid SQL backup. Provided you still have access to your old server, connect to it and re-run the backup:

BACKUP DATABASE TO DISK = '[Backup path here]\sibk.bak' WITH STATS=5


Once done copy it over to your 2016 server and run the restore again.