MIT's Open Courseware initiative, more than a decade old, makes the content of virtually the entire curriculum, more than 2,000 courses in 33 academic disciplines, freely available. The content , released through education on MIT's academic campus, is excluded from the EAR and ITAR export controls, and is generally authorized under OFAC sanctions (no specific authorization required) as information and informational material.
Massive Open Online Courses, such as those delivered by edX and Coursera, are different: the courses are actively delivered, forums for interaction among students and teachers are provided, homework is assigned and evaluated, quizzes and tests are administered and graded, and evidence of successful completion is provided.
OFAC sanctions programs reflect the 1988 Berman Amendment (USC 50 §1702(b)(3)) to the International Emergency Economic Powers Act::
(b) The authority granted to the President by this section does not include the authority to regulate or prohibit, directly or indirectly...
(3) the importation from any country, or the exportation to any
country, whether commercial or otherwise, regardless of format or
medium of transmission, of any information or informational materials,
including but not limited to, publications, films, posters, phonograph
records, photographs, microfilms, microfiche, tapes, compact disks, CD ROMs, artworks, and news wire feeds.
Since the sanctions also generally authorize transactions "necessary and ordinarily incident" authorized transactions, it might seem reasonable to assume that MOOC delivery is generally authorized: providing information is generally authorized; course material is information; course-related interaction doesn't create substantive alteration of the course material, and is incidental and necessary for the generally authorized activity.
However, OFAC's guidance is that delivering courses is providing a service, which is not generally authorized, and requires a specific authorization for students in or ordinarily resident in Cuba, Iran, Sudan, Iraq and the Crimea area.
The Iran sanctions include General License G, authorizing US academic institutions to deliver online undergraduate courses ordinarily required for the completion of undergraduate degree programs in humanities, social sciences, law, or business, including introductory science, technology, engineering and math. Iran General License G also allows the transfer of EAR99 technology.