How securely unguessable are GUIDs?

Solution 1:

UUIDs/GUIDs are specified by RFC4122. Although Version 4 UUIDs are created from random numbers Section 6 makes an explicit statement on security:

Do not assume that UUIDs are hard to guess; they should not be used as security capabilities (identifiers whose mere possession grants access), for example. A predictable random number source will exacerbate the situation.

A good discussion of the randomness of GUIDs can also be found in this question:

How Random is System.Guid.NewGuid()? (Take two)

Solution 2:

This is a perfect example of how not to think about a security issue. Unfortunately it is how a majority of developers think about security...

...potentially worth around $3,000,000...are they secure enough ?...

No. A lot of resources can be brought to bear on a problem that has a possible payout of $3M per ticket. That kind of money could attract people with a lot of resources...some very serious people. Using anything that relies on a general purpose random number generator is not very random...thus not very secure. It is more obfuscation than cryptography.

...physical security checks...had to present the passport used...

Again, with that amount of cheddar on the line... I can get you any passport you'd like.

...possible to predict futures ones?...

Yes. The question is...How long would it take ? ...per some unit of processing work.

...If so, how many would you need to see ?...

That depends on what I know about their creation...OS, CPU, etc...and I'm sure I can find somebody at your firm that would be interested in providing some information in exchange for say...$100,000 or, more likely, less.

-- This may all seem a bit overly dramatic, but you are talking about a serious amount of money and it should be protected with a serious amount security. You need a security consulting firm that can help you choose the encryption package you buy for this. Your client should be able to help via their risk management department or their insurer....If not, get your own lawyer...the one you should already have.

Of course, there is very little chance that anything would go wrong with the GUID scheme but if did go all pear shaped...How are you going to tell all those lawyers that your security plan was top notch and they should look elsewhere ?...Trust me, you do not want to be holding the bag if something goes wrong. That would really suck for you.

Edit: On teedyay's comment...

Obtaining a "Get Out of Jail Free" card from the client is always a good idea. If you tell them "We can make it secure in the case of trivial attacks...but we are not a security or cryptography firm." then your job is done and the client is left holding the bag.