I am having a scenario where the AutomaticMigrationDataLossAllowed property of my Configuration class is not working in Entity Framework 6.
I set both the required properties to true, but yet I receive an update exception which states that potential data loss could occur. Ironically, it advices me to set the properties to true that I have already set to true.
Here's how I instantiate my model container (context).
Database.SetInitializer(new ModelInitializer());
Entities = new ModelContainer();
Here's the relevant part of my ModelInitializer class.
internal class ModelInitializer : IDatabaseInitializer<ModelContainer>
{
    private static bool _usedBefore;
    public void InitializeDatabase(ModelContainer context)
    {
        ...
        var migrateInitializer = new MigrateDatabaseToLatestVersion<ModelContainer, Configuration>();
        migrateInitializer.InitializeDatabase(context);
    }
}
And finally, here's my Configuration class.
internal sealed class Configuration : DbMigrationsConfiguration<ModelContainer>
{
    public Configuration()
    {
        AutomaticMigrationsEnabled = true;
        AutomaticMigrationDataLossAllowed = true;
    }
    protected override void Seed(ModelContainer context)
    {
    }
}
My ModelContainer class (the context) basically just has a few properties and classes in it, so I don't think that's relevant to the problem. Here's the declaration though.
internal class ModelContainer : DbContext
{
    ...
}
                Have you tried using the '-Force' parameter in the package manager console?
E.g.
Update-Database -Force -Verbose
                        Are you using separate library for data access??
if yes then you need to provide its name when running query:
Add-Migration -StartUpProjectName "Your DAL Project" MyNewMigration
Update-Database -StartUpProjectName "Your DAL Project" -Verbose
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