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difarris: So, I have a new and fully updated mac, and LoTR 1 runs perfectly on my machine. For some reason, when I try and start LoTR 3 it just immediatley closes with no error message, and when I try to run LoTR 2 I am getting some weird Wine/Gecko messages indicating a failure. I have no clue how to troubleshoot this, so any help would be appreciated. Thanks!
Hello difarris!

There is a known issue with running Mac games using Wineskin, such as games from Lords of the Realm series on macOS 10.13 High Sierra. We are actively working on updating them, but there is no ETA I can provide.

For now, you can try using the workaround described here: http://wineskin.urgesoftware.com/tiki-view_blog_post.php?postId=87