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I'm currently in the middle of developing an application loosely similar to StackOverflow (question/answer based)

Initially, I was using AWS (simple DB and s3) for storage, however that posed several problems, and I've opted to go with SQL - With a view to eventually hosting on SQL Azure.

I was just wondering if I opted for the 1gb database initially, could I increase the size to the 5gb / 10gb databases later on? Or would I have to create a separate new database of this size, and port my data over?

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You cannot go over 1GB, you have to allow it specifically, you will get an error after you attempt to go beyond 1GB.

To increase the max size, execute this T-SQL as shown: 

ALTER DATABASE MyDatabase MODIFY (EDITION='WEB', MAXSIZE=5GB)

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