root = logging.getLogger()
root.addHandler(TimedRotatingFileHandler("test.log", when="S", backupCount=2, delay=True))
root.addHandler(TimedRotatingFileHandler("test.log.json", when="S", backupCount=1, delay=True))

import logging
import datetime
from logging.handlers import TimedRotatingFileHandler
from tempfile import TemporaryDirectory
from pathlib import Path
from time import sleep

with TemporaryDirectory() as td:
    tmp_path = Path(td)
    filename = "test.log"
    filename_json = f"{filename}.json"
    logfile = tmp_path / filename
    logfile_json = tmp_path / filename_json

    h1 = TimedRotatingFileHandler(logfile, when="S", backupCount=2, delay=True)
    h2 = TimedRotatingFileHandler(logfile_json, when="S", backupCount=1, delay=True)
    times = []
    for log_str in ("hi1", "hi2", "hi3", "hi4"):
        times.append(datetime.datetime.now().strftime("%Y-%m-%d_%H-%M-%S"))
        for h in (h1, h2):
            h.emit(logging.LogRecord("name", logging.INFO, "path", 1, log_str, (), None))
        sleep(1)
    assert logfile.is_file()
    actual = set(f.name for f in tmp_path.iterdir())
    expected = {
        "test.log",
        f"test.log.{times[-3]}",
        f"test.log.{times[-2]}",
        "test.log.json",
        f"test.log.json.{times[-2]}",
    }
    assert actual == expected, (
        f"\n\texpected:\t{','.join(expected)}" f"\n\tactual:\t\t{','.join(actual)}"
    )
    assert logfile.read_text() == "hi4\n"
    assert logfile_json.read_text() == "hi4\n"
    assert (tmp_path / f"{filename}.{times[-3]}").read_text() == "hi2\n"
    assert (tmp_path / f"{filename_json}.{times[-2]}").read_text() == "hi3\n"