Can WitnessWork remind me to log time for a day I planned?

Yes. Go to Preferences → Plans, turn on Remind Me to Log Time, and choose a Remind At time (8:00 PM unless you change it). If a day has a plan but no time logged, you get one reminder at that time after the day's plans end: a morning plan reminds you that evening, and a plan still going at your Remind At time reminds you the next day. Several plans on the same day give one reminder, and when two days' reminders would arrive at the same time they're combined. Logging any time for that day stops its reminder and clears one you've already received; removing that day's plans or turning the setting off does too. A day planned with no time doesn't remind you, and days you missed before turning the setting on aren't included. Tapping the reminder opens Add Time with the date, planned time, and type already filled in. The reminder is also listed in the Home bell for a week, even if system notifications are off. The setting appears when you track hours; Regular Publishers turn on Log my hours first. Turning it on asks for notification permission, or opens your device settings if you've declined before. Reminders are worked out on your device from your own plans and time and aren't sent anywhere. Each device schedules its own reminders up to two weeks ahead, so open WitnessWork at least every two weeks to keep them coming. If you log time on another device, open WitnessWork on this one so it can cancel that day's reminder. On Android, the system may deliver a reminder a few minutes late to save battery. If reminders don't arrive, check that notifications are allowed for WitnessWork in your device settings (on Android, including its Reminders category) and that Focus or Do Not Disturb isn't silencing them. If they still don't arrive, report the problem from the Help Center without including names or other private details.