Is it possible for ASP.NET to mix up which user is associated with which session variable on the server? Are session variables immutably tied to the original user that created them across time, space & dimension?
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To answer your original question: Sessions are keyed to an id that is placed in a cookie. This id is generated using some random number crypto routines. It is not guaranteed to be unique but it is highly unlikely that it will ever be duplicated in the span of the life of a session. Even if your sessions run for full work days. It would probably take years for a really popular site to even generate a duplicate key (No stats or facts to back that up).
Having said all that it doesn’t appear that your problem is with session values getting mixed up. The first thing that I would start to look at is connection pooling. ADO pools connections by default but if you request a connection with a username/password that is not in the pool it should give you a new connection. Hint that may be a performance bottleneck in the future if your site is very large. It has been a while since I worked with SQL Server, in Oracle there is a call that can be made to switch the identity of the user. I would be surprised if there was no equivalent in SQL Server. You might try connecting to your DB with a generic username/password and then executing that identity switch call before you hand back the connection to the rest of your code.