> > Under no circumstances it should ever happen that "high secret 
> > attachment" of user A has the same checksum of "funny pic" 
> from user 
> > B, and the DB makes a link for user B to "high secret 
> attachment" of 
> > user A.
> 
> Definitely. We need an algorithm that will prevent collisions 
> at all cost. Such checksums will only be calculated during 
> insertion to ensure uniqueness of the attachment so they will 
> not affect the retrieval processes (pop/imap).
> 
> That said, "high secret" stuff should of course have been 
> encrypted to begin with.

How about just taking x size hunk from start and from end of the file, then
md5sum both of them? I think that possibility that you will get 2 exactly
same md5 hash is quite zero..

Bonus comes that you don't need to do md5 hash from whole file, so server
should not suffer performance loss because of this.

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