First an example: suppose we are on a $2$-sphere, and we have two vector fields $X,Y$ on it. Then, suppose that we want to rotate all vectors of $X$ by $\frac{\pi}{2}$ with respect to the outer normal:
in spherical local coordinates ($\theta\in (0,\pi)$, $\varphi\in (0,2\pi)$), this rotation corresponds to the matrix $R(\theta)=\begin{bmatrix}0 & -\sin(\theta)\\\frac{1}{\sin(\theta)}& 0\end{bmatrix}$. We would like to compute $\nabla_Y(R(\theta)X)$.
My question: is there any property of the covariant derivative that allows me to compute easily $\nabla_Y(A(x)X)$, where $A$ is some coordinates dependant matrix acting in local coordinates on $Y$?
Something that generalise $\nabla_Y(fX)=Y(f)X+f\nabla_Y(X)$ to matrices.
Here the problem is that the matrix actually mix together the vector components $\frac{\partial}{\partial X_i}$.
To answer your question about rotation: First, the rotation $R$ by $\pi/2$ along the normal vector $\vec n$ is given by
$$ R (X) =\vec n \times X,$$ where $\times $ is the cross product in $\mathbb R^3$. For any other $Y$,
\begin{align} Y( R(X) ) &= \nabla_Y (\vec n \times X) \\ &= Y(\vec n) \times X + \vec n \times Y(X). \end{align}
By $Y(R(X))$ and $Y(X)$ I mean the componentwise differentiation. Note that $\nabla _YX = (Y(X))^T$ by definition of $\nabla$. For the $2$-sphere, $x\mapsto \vec n(x)$ is indeed the immersion $\mathbb S^2 \subset \mathbb R^3$. Thus $Y(\vec n) = Y$. Also, $\vec n \times Y(X) = \vec n \times \nabla_Y X$, so
$$Y(R(X)) = Y\times X + R(\nabla_YX)\Rightarrow \nabla_Y(R(X)) = R(\nabla_YX).$$
We can do something similar for any immersed surface $M$ in $\mathbb R^3$. We still have $R(X) = \vec n \times X$ and
$$ Y(R(X)) = Y(\vec n) \times X + \vec n \times \nabla_YX. $$
This time $Y(\vec n) = A(Y)$, where $A$ is the shape operator, which maps tangent vectors to tangent vectors. In particular, $A(Y) \times X$ is orthogonal to your surface, thus we also have $$ \nabla _Y(R(X)) = R(\nabla_YX).$$
In general, for any $\theta$, the rotation $R(\theta)$ is given by
$$R(\theta) X = \cos \theta X + \sin \theta R(X).$$
Thus
\begin{align} \nabla_Y ( R(\theta)(X)) &= \cos \theta \nabla _Y(X) + \sin\theta \nabla_Y( R(X)) \\ &= \cos \theta \nabla _Y(X) + \sin\theta R(\nabla_YX) \\ &= R(\theta) (\nabla_YX). \end{align}
Thus for any immersed surface $M$ in $\mathbb R^3$, the rotation $R(\theta)$ commutes with covariant derivatives.