This is the first time I am installing League onto this iMac and I have tried looking for solutions online but they seem to not be working. Hope you can help! Tl;dr: When I download lol for first time on new mac it launches then disappears and the icon of the league of legends application in the apps folder is a circle with a line through it.

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After fresh install of League of Legends on macOS with case-sensitive APFS volume it's not possible to start League of Legends game, after champion selection the launcher won't open the game client and is stuck with reconnect button.

Terminal method is probably more reliable as you can see real file names within terminal opposite to Finder which 'beautifies' them so you can't be sure what the actual file name is.

Note that League patcher will probably install updates under old filename so it's possible that these steps will need to be taken after every patch until Riot fixes it.

Download Mac Launcher

Terminal.app

1. Open Terminal.app from Applications
2. Browse to League contents with cd /Applications/League of Legends.app/Contents/LoL/RADS/solutions/lol_game_client_sln/releases/
3. At this point you need to list this directory's content to find most recent release number with ls
4. Navigate to release's content: cd 0.0.1.49/deploy/. Replace release with the one from step 3
5. Run mv LeagueofLegends.app LeagueOfLegends.app

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Finder

New League Launcher

1. Open Finder
2. Press Cmd+Shift+G
3. Type /Applications/League of Legends.app/Contents/LoL/RADS/solutions/lol_game_client_sln/releases/
4. Open directory with most recent release
5. Open deploy directory
6. Right click League Of Legends and choose Rename
7. Remove all spaces from the name so it looks like LeagueOfLegends and press Return
8. As mentioned before, Finder doesn't display file's real name so after renaming it will still display the old name. However, real file name should be changed

Turns out it's an issue with Apple's new APFS file system which changes handling of some filenames.Looking into client logs we can find:

This hints that launcher simply cannot find client's app.Few lines above this one we can see what path launcher is looking for:

The problem lies with client app in deploy directory. Taking a look at deploy contest after fresh install on APFS volume we'll find 'LeagueofLegends.app'. However, launcher looks for 'LeagueOfLegends.app'.

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Simply renaming app fixes the issue.