Privilege authentication systems and techniques for communications to confinement institution inmates

A system comprising:

• a processor;
• a non-transitory computer readable medium comprising instructions that, when executed via the processor, cause the system to perform operations comprising:
• receiving an electronic communication via a computing network from a sender, wherein the electronic communication comprises a first image depicting a postal item to be sent to an inmate of a confinement institution, the first image captured prior to sending the postal item to be sent;
• determining that the sender is a person having a privileged status;
• receiving a second image captured after a received postal item is received at a receiving facility, the second image depicting the received postal item;
• verifying, via an image-to-image comparison, that the received postal item depicted in the second image matches the postal item to be sent depicted in the first image, wherein the verifying comprises segmenting the first image and the second image to remove background and non-postal item portions, identifying features within postal item portions of the first image and the second image, comparing the identified features, and requiring a threshold confidence level in a match;
• and
• based on the determining that the sender is a person having the privileged status and the verifying that the received postal item depicted in the second image matches the postal item to be sent depicted in the first image, determining to apply a privileged communication status to the received postal item.