diff --git a/src/auth.zig b/src/auth.zig
index 8bd7621..afc54ef 100644
--- a/src/auth.zig
+++ b/src/auth.zig
@@ -501,14 +501,25 @@ fn executeCmd(global_log_file: *LogFile, allocator: std.mem.Allocator, shell: []
     return std.posix.execveZ(shell_z, &args, std.c.environ);
 }
 
-fn redirectStandardStreams(global_log_file: *LogFile, session_log: []const u8, create: bool) !std.fs.File {
-    const log_file = if (create) (std.fs.cwd().createFile(session_log, .{ .mode = 0o666 }) catch |err| {
+fn createSessionLogFile(global_log_file: *LogFile, session_log: []const u8) !std.fs.File {
+    // Create parent directories for the session log file if they don't exist
+    if (std.fs.path.dirname(session_log)) |session_log_dir| {
+        try std.fs.cwd().makePath(session_log_dir);
+    }
+    return std.fs.cwd().createFile(session_log, .{ .mode = 0o666 }) catch |err| {
         try global_log_file.file_writer.interface.print("failed to create new session log file: {s}\n", .{@errorName(err)});
         return err;
-    }) else (std.fs.cwd().openFile(session_log, .{ .mode = .read_write }) catch |err| {
-        try global_log_file.file_writer.interface.print("failed to open existing session log file: {s}\n", .{@errorName(err)});
-        return err;
-    });
+    };
+}
+
+fn redirectStandardStreams(global_log_file: *LogFile, session_log: []const u8, create: bool) !std.fs.File {
+    const log_file = if (create)
+        (try createSessionLogFile(global_log_file, session_log))
+    else
+        (std.fs.cwd().openFile(session_log, .{ .mode = .read_write }) catch |err| {
+            try global_log_file.file_writer.interface.print("failed to open existing session log file: {s}\n", .{@errorName(err)});
+            return err;
+        });
 
     try std.posix.dup2(std.posix.STDOUT_FILENO, std.posix.STDERR_FILENO);
     try std.posix.dup2(log_file.handle, std.posix.STDOUT_FILENO);