Free-space optical systems are emerging for high data rate communication and transfer of information in indoor and outdoor settings. However, free-space optical communication becomes challenging when an occlusion blocks the light path. Here, we demonstrate, for the first time, a direct communication scheme, passing optical information around a fully opaque, arbitrarily shaped obstacle that partially or entirely occludes the transmitter's field-of-view. In this scheme, an electronic neural network encoder and a diffractive optical network decoder are jointly trained using deep learning to transfer the optical information or message of interest around the opaque occlusion of an arbitrary shape. The diffractive decoder comprises successive spatially-engineered passive surfaces that process optical information through light-matter interactions. Following its training, the encoder-decoder pair can communicate any arbitrary optical information around opaque occlusions, where information decoding occurs at the speed of light propagation. For occlusions that change their size and/or shape as a function of time, the encoder neural network can be retrained to successfully communicate with the existing diffractive decoder, without changing the physical layer(s) already deployed. We also validate this framework experimentally in the terahertz spectrum using a 3D-printed diffractive decoder to communicate around a fully opaque occlusion. Scalable for operation in any wavelength regime, this scheme could be particularly useful in emerging high data-rate free-space communication systems.