I've had this issue before and when i switched to HLSR i stopped having the issue, so I never found a fix. My livesplit will not start automatically and it will also not finish automatically. All other maps will autosplit, just not first and last. Are there known fixes? I know other people have had this issue.

You can check if autostart/end is enabled in the autosplit settings. Try running splits as administrator. If just as an administrator does not help, try going to the splits editor and activate/deactivate AutoSplit several times.

Thanks for the suggestions! It turns out downloading the 3.3.3 version of Sourcesplit fixed the problem.