It was pretty hard finding a short and precise title. Here is my problem:
The equation $$\bigg|\int_\gamma f(z)\text{d}z\bigg|\le\int_\gamma\big|f(z)||\text{d}z|$$ holds if $f$ is integrable (where $\gamma$ is a differentiable path $[0,1]\rightarrow\mathbb{C}$). However, in what cases does "$=$" apply? Some cases are clear; for example if $f(z)=$const, $\forall z\in {\rm Img}(\gamma)$.
Our second idea was that both sides are equal if (or even iff?) $f(z)$ stays within one quadrant of the complex plane for all points in ${\rm Img}(\gamma)$.
So basically, the question is, when does "$=$" apply and is our second idea correct? Use "if" or "iff" (which is if and only if). Is there a nice proof to whatever answer there is? (No need to print the full proof; the basic idea suffices)
EDIT: instead of using the path definition of the integral, here is the corrected version: $$\bigg|\int_0^1f(\gamma(t))\gamma'(t)\text{d}t\bigg|\le\int_0^1|f(\gamma(t))||\gamma'(t)|dt.$$
It suffices to consider the following reduced question: if $g:[0,1]\to\mathbb{C}$ is Riemann/Lebesgue integrable, in the following inequality $$\left|\int_0^1g(t)dt\right|\le \int_0^1|g(t)|dt,\tag{1}$$ when does "$=$" holds?
To answer this question, let us recall how to deduce $(1)$. Since if $g$ is Riemann integrable on $[0,1]$, it is automatically Lebesgue integrable, so let us focus on the Lebesgue integrable case. Denote $I=\int_0^1g(t)dt$. If $I=0$, then $(1)$ is trivially true, and "$=$" holds if and only if $g=0$ almost everywhere. If $I\ne 0$, then there exists a unique $\alpha\in\mathbb{C}$ with $|\alpha|=1$, such that $I=|I|\alpha$. Therefore, $$|I|=\overline{\alpha}I=\mathrm{Re}(\overline{\alpha}I)=\mathrm{Re}\int_0^1\overline{\alpha}g(t)dt=\int_0^1\mathrm{Re}(\overline{\alpha}g(t))dt\le\int_0^1|g(t)|dt.$$ Note that for the last inequaltiy, "$=$" holds if and only if $\mathrm{Re}(\overline{\alpha}g(t))=|g(t)|$ for almost every $t\in[0,1]$, i.e. $g(t)=\alpha|g(t)|$ for almost every $t\in[0,1]$. To sum up, "$=$" in $(1)$ holds if and only if there exists $\alpha\in\mathbb{C}$ with $|\alpha|=1$, such that $g(t)=\alpha|g(t)|$ for almost every $t\in[0,1]$. To go back to your original question, simply let $g(t)=f(\gamma(t))\gamma'(t)$.