@oyam@aaronpk Gogo recommends turning off iMessages in their guide, so I’d assume it has to do with that. It’s probably causing iMessages to fail completely and iMessages is falling back to SMS (unless you had that explicitly disabled?).
@aaronpk I don't think they're looking at the packet but maybe iMessage has a different endpoint to which images get uploaded and that's blocked? They could very well have taken Apple's approval and blessings to do this, since that's their business plan. // @sirshannon