With free space optical (FSO) communication systems, information is generally transmitted to minimize diffraction. Here, we demonstrate an alternate paradigm, "diffractal space-division multiplexing" (DSDM), in which the diffraction of fractals enable a wider cone for reception to support roaming transceiver. As a result, DSDM is robust to misalignment over longer-distance links. We examine the consequence of mid-field, non-far-field propagation and the result on kernel bit error rates. The sparse and redundant encoding of information in DSDM may be relevant to other FSO acquisition, pointing, and tracking.