diff --git a/source/common/initfs.cpp b/source/common/initfs.cpp
index 597c476da..3c566d97c 100644
--- a/source/common/initfs.cpp
+++ b/source/common/initfs.cpp
@@ -320,13 +320,14 @@ void InitFileSystem(TArray<GrpEntry>& groups)
 			FString newname = fn + fname;
 			D_AddFile(Files, newname);
 		}
+		bool insert = (!insertdirectoriesafter && &grp == &groups[0]) || (insertdirectoriesafter && &grp == &groups.Last());
 
 		// Add the game's main directory in the proper spot.
-		if ((i == (insertdirectoriesafter ? 0 : dependencies.Size() - 1)) || grp.FileInfo.loaddirectory)
+		if (insert)
 		{
 			// Build's original 'file system' loads all GRPs before the first external directory.
 			// Do this only if explicitly requested because this severely limits the usability of GRP files.
-			if (insertdirectoriesafter && i == 0) for (auto& file : *userConfig.AddFilesPre)
+			if (insertdirectoriesafter) for (auto& file : *userConfig.AddFilesPre)
 			{
 				D_AddFile(Files, file);
 			}
diff --git a/source/common/searchpaths.cpp b/source/common/searchpaths.cpp
index 085ff873b..06d67703d 100644
--- a/source/common/searchpaths.cpp
+++ b/source/common/searchpaths.cpp
@@ -1086,7 +1086,7 @@ const char* G_DefaultConFile(void)
 
 	if (g_gameType & GAMEFLAG_WW2GI)
 	{
-		if (fileSystem.FindFile("ww2gi.con")) return "ww2gi.con";
+		if (fileSystem.FindFile("ww2gi.con") >= 0) return "ww2gi.con";
 	}
 
 	if (g_gameType & GAMEFLAG_SW)
@@ -1094,14 +1094,14 @@ const char* G_DefaultConFile(void)
 
 	if (g_gameType & GAMEFLAG_NAM)
 	{
-		if (fileSystem.FindFile("nam.def")) return "nam.def";
-		if (fileSystem.FindFile("napalm.def")) return "napalm.def";
+		if (fileSystem.FindFile("nam.con") >= 0) return "nam.con";
+		if (fileSystem.FindFile("napalm.con") >= 0) return "napalm.con";
 	}
 
 	if (g_gameType & GAMEFLAG_NAPALM)
 	{
-		if (fileSystem.FindFile("napalm.def")) return "napalm.def";
-		if (fileSystem.FindFile("nam.def")) return "nam.def";
+		if (fileSystem.FindFile("napalm.con") >= 0) return "napalm.con";
+		if (fileSystem.FindFile("nam.con") >= 0) return "nam.con";
 	}
 
 	// the other games only use game.con.