Upsizing an Access database only works on a local network. You would need to install SQL Server Express and Access on your PC, do the upsize and then backup the database and have it restored to your web hosts servers.
The only reason for this loop to keep occurring is if the files in the database folder can not be written to to record your database connection properties. This would be caused by a permission issue and you should check that the user account for the application pool your website runs under has read, write and modify permissions both on the directory itself and the files within.
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