Wolfram says, there are only two roots, but $\sqrt{i}$ already gives two roots. So if we express them in Cartesian form we can take square roots of them separately and end up with four roots.
$$\sqrt{i}=e^{\frac{i\pi}{4}}=\frac{1}{\sqrt2}+i\frac{1}{\sqrt2}$$ But also $$\sqrt{i}=e^{\frac{-3i\pi}{4}}=-\frac{1}{\sqrt2}-i\frac{1}{\sqrt2}$$ Then take square roots of each of those and you end up with $$\sqrt{\sqrt{i}}=e^{\frac{i\pi}{8}},e^{\frac{5i\pi}{4}},e^{\frac{-3i\pi}{4}},e^{\frac{-7i\pi}{4}}$$
It works, doesn't it? Raise each of those to the power of 4 and you get $i$. What am I missing here?
Your list of four solutions only has two - as has been pointed out you listed two of them twice. (In the original post, anyway...) But there are four roots.
First, $i=e^{i\pi/2}=e^{i5\pi/2}$ leads gives two values for $\sqrt i$, namely $e^{i\pi/4}$ and $e^{i5\pi/4}$. Each of these has two square roots: Since $e^{i\pi/4}=e^{i9\pi/4}$ it has the two square roots $e^{i\pi/8}$ and $e^{i9\pi/8}$. Similarly $e^{i5\pi/4}=e^{i13\pi/4}$ has the two square roots $e^{i5\pi/8}$ and $e^{i13\pi/8}$. For a total of four values of $\sqrt{\sqrt i}$, namely $$e^{i\pi/8},e^{i5\pi/8},e^{i9\pi/8},e^{i13\pi/8}.$$
NOTE Others have suggested that although a complex number has two square roots, the notation $\sqrt z$ refers to only one of them. I think it's wrong to put it that way; that notation refers to only one of them if we have clearly stated in advance which "branch" we're referring to. But Wolfram is wrong in any case. By my lights, $i$ has two square roots, each of which has two square roots, for a total of four as above. But if we are saying that the notation $\sqrt z$ refers to one square root, then Wolfram should say there's only one value for $\sqrt{\sqrt i}$, namely the one square root of the one square root.
I think four is the right number. With that convention there's only one; there's no sensible way to give exactly two values, as WA does. You can't believe everything they tell you.