A retinal imaging system includes an eyepiece lens assembly, an image sensor, a dynamic fixation target viewable through the eyepiece lens assembly, and a controller coupled to the image sensor and the dynamic fixation target. The controller includes logic that causes the retinal imaging system to perform operations including: acquiring a first image of the eye, analyzing the first image to determine whether a lateral misalignment between the eye and the eyepiece lens assembly is greater than a threshold misalignment, in response to determining the lateral misalignment is greater than the threshold misalignment, adjusting a visual position of the dynamic fixation target to encourage the eye to rotate in a direction that compensates for the lateral misalignment, and acquiring the retinal image of the eye while the eye is encouraged to rotate towards the direction that compensates for the lateral misalignment.