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This may not be a perfectly generalized solution, but is it possible to structure your system such that when upgrading from version i to version i+1, version i of your app is compatible with both versions i and i+1 of your database and vice versa?

Say, for example, your factoring a column into it's own table. Don't just drop the column, set up a trigger to synchronize the original column value with a value from one of the rows in your new table.

You could then finally drop the column in version i+2.

I seem to remember finding a book on database refactorings that covered this technique in more detail. It was online so you could try Googling for it.



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