Long comment This can indeed be accomplished with the help of the residue theorem, although it requires a lot of massaging of the starting integral. We can begin by rewriting
$$\begin{align*}
I &= \int_0^{2\pi} \tan\frac t8 \, dt \\
&= 4 \int_0^\tfrac\pi2 \tan\frac t2 \, dt & t\to4t;\text{ symmetry} \\
&= 4 \int_0^\infty \tan\left(\frac12 \arctan u\right) \, \frac{du}{1+u^2} & u=\tan t \\
&= 2\pi - 4 \underbrace{\int_0^\infty \overbrace{\frac{\arctan u}{\sqrt{1+u^2} \left(1+\sqrt{1+u^2}\right)}}^{f(u)} \, du}_J & \text{by parts}
\end{align*}$$
The integral of $f$ can be done by considering $f(u)\log u$ on an appropriate keyhole contour. On the other hand, we may slightly simplify the integrand by partially evaluating as follows (although the resulting integral's evaluation via residues is a bit more complicated due to introduced poles):
$$\begin{align*}
J &= \int_0^\infty \int_0^1 \frac u{1+u^2v^2} \, \frac{dv\,du}{\sqrt{1+u^2} \left(1+\sqrt{1+u^2}\right)} \\
&= \int_0^1 \int_1^\infty \frac{dU\,dv}{(U+1) \left(1+\left(U^2-1\right)v^2\right)} & \text{Fubini; }U=\sqrt{1+u^2} \\
&= \int_0^1 \left[\frac{v\arccos v}{\sqrt{1-v^2}} - \log(2v)\right] \, dv \\
&= 1 - \log2 + \int_0^\infty \frac{w \left(\frac\pi2-\arctan w\right)}{\left(1+w^2\right)^{3/2}} \, dw & w=\frac v{\sqrt{1-v^2}} \\
&= 1 - \log2 + \int_0^\infty \overbrace{\frac{\arctan w}{\left(1+w^2\right)^{3/2}}}^{g(w)} \, dw & w\to\frac1w
\end{align*}$$
Again we may consider the integral of $g(w)\log w$; see here and here for similar exercises.
Either way, this particular procedure generates more tricky integrals. Applying the residue theorem to the two cases above leads to the following integral identities that IMO are more trouble than they're worth:
$$\begin{align*}
\int_0^\infty f(u)\,du &= 1 + \frac1\pi \int_0^1 \frac{u \log u \log\frac{1+u}{1-u}}{\sqrt{1-u^2}} \, du = \frac\pi2-\log2 \\[2ex]
\int_0^\infty g(w)\,dw &= \frac1\pi \int_0^1 \frac{w \log w \log\frac{1-w}{1+w}}{\left(1-w^2\right)^{3/2}} \, dw = \frac\pi2-1
\end{align*}$$