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If you are sent to Wolfskull Cave as part of a radiant quest (such as Shalidor's Insights), you will not be able to complete the radiant quest while The Man Who Cried Wolf is active. You will need to first finish The Man Who Cried Wolf and wait for the dungeon to reset.
https://en.uesp.net/wiki/Skyrim:Wolfskull_Cave
Anyway, it turns out that other people have experienced this issue in the past - mostly *years* in the past, but the solution there worked for me:
"found it... somehow the hole was sealed with ice.. I actually had to cheat (with tcl) and float through the floor. Then I was able to finish the quest. "
https://steamcommunity.com/app/72850/discussions/0/846944689740134820/
So this issue has been resolved.
I usually hit it prior to starting the quest to get a shot at loot.
Follow up. Does anyone elses companions not come in with them (Either before or during quest). They will show up in the next area but not the first one.