In chrome you can often force auto play by playing a sound (and having that fail) and then playing another sound right after that. Maybe IOS has a similar loophole?
Is there some kind of legitimate reason it has to work this way that this workaround takes advantage of, or is it just an oversight/bug?
How you're describing it it sounds like they only block the first sound you try to auto play - if the latter is the reason then that's really surprising.