AI Can’t Plan Your Whole Day—Not Yet—But We Found One App That Gets Close

I’ve been testing and writing about software professionally since 2010. Over that time, I’ve tested a wide range of productivity software, including once reviewing more than 50 project-management apps for a single guide.

At any given time, I manage tasks across my calendar, email accounts, to-do list apps, notes tools, and Slack while juggling three core projects and a handful of other commitments. If AI could tame any task-management mess, mine would be the one to tackle.

For this guide:

• I spent 24 hours researching and testing nine AI scheduling tools available on web, desktop, and mobile, using their automations to plan my day with integrations to pull in events and tasks from other apps.
• I consulted three time-management experts: Marc Zao-Sanders, author of Timeboxing: The Power of Doing One Thing at a Time; Nancy Colter, instructor of Emory University’s “Managing Your Time and Productivity” course; and Neha Kirpalani, a Harvard Business Review writer who focuses on productivity and timeboxing. I also corresponded with New York Times technology reporter Kashmir Hill about her experiment in putting AI in charge of her life for a week.
• Like all Wirecutter journalists, I review and test products with complete editorial independence. I’m never made aware of any business implications of my editorial recommendations. Read more about our editorial standards.

Life is messy. Rarely is everything you need to do in one place. Work tasks are scattered across calendars and project-management apps, assigned in GitHub issues and Figma comments, hidden in Google Docs suggested edits and Slack messages. Then there’s the rest of life, and all the other things you need to manage—medical appointments, grocery orders, bill payments, and so on, all of which are easy to overlook when your day is planned out on a work to-do list.

Tasks themselves contain a multitude of demands on your time. “Email your accountant” could consist of a two-minute reply or an hour-long search for a missing document. “Write an article” is a project-sized task that contains many discrete steps, from research to writing to self-editing. It has bedeviled many a writer—let alone today’s rudimentary AI models.

In theory, AI task-scheduling software is for anyone juggling life and work tasks across multiple to-do lists and calendars. If you’ve ever accidentally scheduled overlapping meetings in your personal and work calendars, or if you typically struggle to find time to fit all of your tasks in your day, AI task-scheduling software should help you avoid that. It should keep you more focused on work and allow you worry less about things falling through the cracks.

In our tests, it did those things—to a degree. These apps shine as universal inboxes for tasks, collecting everything you need to do from email and chat clients, project-management software, and more. And they can automatically determine when you should do a task and schedule accordingly.

But in our testing, AI task-scheduling software generally failed to make a difference in what I was able to accomplish. Yes, these apps scheduled time for me to do a task. But that didn’t necessarily mean I’d get to the task at that time or find myself working on the most important task at that moment.

In one sense, AI fails at scheduling tasks due to a lack of data. It can intuit, for example, that an “Email accountant” task is finance-related, or estimate that “an email” should take around five minutes to write, but it can’t divine a task’s full requirements or its relative priority unless you outline every detail.

And if you have to go to that much trouble, you might as well schedule the task yourself. After all, it’s just one additional click. But that isn’t the only reason AI comes up short.

Manual scheduling may be key to actually getting things done. Every time-management expert we spoke with told us that the act of choosing what to work on and when to work on it helps people get their most important work done.

“Scheduling specific tasks helps with focus and accountability, reducing the risk of procrastination,” said time-management expert Nancy Colter. Author and expert Marc Zao-Sanders agreed, noting, “Choosing what to do and when to do it manually fosters and affirms agency.” He added that such agency is what everyone needs “to feel worthwhile and responsible for what’s going on in our lives.”

AI promises to plan your day and save you time—and someday in the future, it may actually do so. Thinking through your tasks, though, might be the best use of your time. It’s how you can wrest agency from a schedule that may often seem out of your control.

Today’s AI task-scheduling tools are best used as a space for you to think more carefully about how you use your time. With a universal inbox for your tasks, paired with tools to review tasks before you start the day and notify you when it’s time to move on to the next one, you’ll become more keenly aware of how time flies. And when you turn everything into a scheduled task, you’ll realize how much “quick” email replies and Slack requests fill up your day with busywork instead of progress.

“At any given moment of any given day, there’s one thing you’ve said you should be focused on, not two or three or seven or a hundred,” said Zao-Sanders. How should you decide which task to do at that time? “My advice is to do it yourself.”

AI doesn’t understand context. In our testing, when I carefully defined tasks, listed their priority, and categorized them into goals, AI was good at scheduling them. But it was less accurate at guessing how long they would take, let alone the effort required to accomplish them.

Structured, for example, estimates an “energy level” for how much effort a task requires. But in my experience, it listed “going for a run” (something that I find gives me mental energy) as high energy, while listing a two-hour writing sprint (a task much more likely to leave me feeling drained) as low energy. Such results, of course, vary wildly from person to person.

AI tools are “helpful for automating routine scheduling, and identifying open time blocks,” said Colter, but they lack “the human judgement needed to prioritize based on urgency, energy levels, and strategic goals.” That prevents them from effectively choosing what’s most important for you to do next.

Popular to-do and project-management apps are rapidly adding AI features. Most task- and project-management mainstays do not use AI to schedule tasks today. But it would be naive to assume that they won’t in the future.

The kanban app Trello recently announced a universal task inbox to aggregate work from Gmail, Slack, and more. That Trello feature and our to-do list app pick, Todoist, both offer AI-powered tools for you to brainstorm ideas and break tasks into more actionable sub-tasks. And smart features such as natural-language parsing and recurring tasks have been standard in to-do list apps for years. It would be a small stretch to imagine their offering AI task scheduling in the future, as well.

We do not recommend switching productivity systems solely for automated task scheduling—not today, anyhow. ChatGPT, Claude, and other AI large language model (LLM) tools are improving so quickly, today’s recommendations could become obsolete tomorrow. But the features that may be worth the switch—a universal task inbox and meeting-scheduling tools—require only AI’s close cousin, automation.

The AI premium is not worth paying yet. Todoist costs $5 a month. TickTick—Wirecutter’s budget-pick to-do list app—costs $36 a year. Both also offer free, basic plans.

Every AI task-scheduling app we tested was priced higher than that, ranging from $5 per month for Structured’s Pro plan with AI features to as much as $29 per month for Motion or $34 per month for Akiflow. (The only exceptions were Reclaim AI’s free Lite plan and Antispace, which is free in beta.)

That premium may be worth paying for anyone who’s juggling an especially busy schedule, if the integration-powered universal task inbox keeps you from forgetting critical tasks. But the price is difficult to justify for the AI features alone.

“Copilot is a mixed bag,” Wirecutter senior staff writer Max Eddy wrote about the AI button built into many newer PC laptops. “So far I’ve found it slow, unpredictable, and questionably useful.” He found the same with the iPhone’s AI features, saying, “They’re (mostly) unremarkable.”

After testing today’s AI task-scheduling apps in depth, we came to the same verdict.

Sunsama promises that it can “make work-life balance a reality.” No app can actually do that for you—at least, not on its own—but after I tried managing my schedule in Sunsama for a few weeks, I found that it did push me to build a healthier relationship with work.

It does the tedious task management for you, pulling tasks and appointments from email, calendar, and productivity apps, reminding you to plan your day, and rescheduling tasks when you can’t finish everything. Then it’s up to you to prioritize the tasks, organize them, and ask Sunsama to move them into available time slots.

It isn’t as automated as competing AI task-scheduling apps, and both learning the app and planning out your daily schedule take time. It’s also expensive in comparison with traditional to-do list apps, at $20 per month. For that investment, you get a calmer, journal-focused take on task management that won us over in testing—even as we concluded that AI-powered task scheduling is not the best option for most people today. Instead of attempting to automate everything, it helps you approach work more mindfully and prevents critical work from falling through the cracks.

It forces you to think about your tasks. Sunsama is more a planner than a to-do list. Each morning, it reminded me of tasks I didn’t complete the previous day, along with tasks I had planned to work on that day, helping me prioritize which tasks to work on and which ones to save for later.

It then showed my predicted workload for the day, counting both tasks and meetings, along with my preferred shutdown time—and it would warn me if my day was overbooked. It also nudged me to write down anything important for the day, in addition to offering a space for me to think about any obstacles impeding my progress.

Throughout the day, Sunsama pushes you to put the same level of thought into each task. At first, I would check off tasks in the calendar view, similar to my approach in other to-do list apps. But I quickly came to like its Focus mode, which hides all other tasks, giving you instead a space to add notes, check off sub-tasks, and track the time you’re spending on that task. Complete a task, and the next task automatically comes into view.

It’s a universal inbox for tasks. Sunsama integrates with lots of external apps that today’s professionals commonly use, including:

• Gmail and Outlook for both email and calendars
• Microsoft Teams and Slack for turning chat messages into tasks
• GitHub, Jira, and Linear for working on developer-focused issues
• Notion for working on notes
• Apple Reminders, Asana, ClickUp, Todoist, Toggl, and Trello to pull in tasks from those popular to-do list apps

Pulling in tasks from Todoist and Trello worked as expected, and being able to add pull requests and issues from GitHub or messages from Slack to my task list was a nice extra. The Gmail integration was the one I came to find most indispensable, though, since it allowed me to drag actionable emails onto my to-do list and see the full message contents without needing to open Gmail separately.

When you’re wrapping up the day, Sunsama pulls in anything you worked on in integrated apps to build a full picture of your workday. This feature helped me see where the time went on a day in which I had cleared off a number of emails and pushed a couple of GitHub pull requests but hadn’t added any tasks directly to Sunsama.

It has small, useful AI integrations. Auto-scheduling tasks is the headline feature for AI task-scheduling apps—but Sunsama doesn’t schedule all of your tasks automatically. Instead, when planning your day, you hover your mouse over a task and then press X on your keyboard to prompt Sunsama to schedule it in the next available slot.

If you check off a task earlier than expected, if tasks take longer than anticipated, or if something comes up and you schedule a new task on top of an existing task’s time, Sunsama adjusts your task schedules as appropriate. And it can automatically add gaps between tasks for a buffer to catch your breath.

AI plays a role when you’re adding new tasks, too. After it learns which tasks you add to which projects (Sunsama calls them “channels”) and how much time they tend to take, it automatically categorizes and estimates the time for new tasks.

Sunsama also surprised me at times. One day, I scheduled a Gmail email as a task. When I opened my daily report to make a journal entry about what I’d worked on, Sunsama produced an AI-generated summary of the email for a quick reminder of what the task had entailed. It was an unexpectedly delightful use of AI that made my journal entry more complete—even if it wasn’t exactly critical to my workflow.

Other features are more subtle automations. Sunsama will keep you from overbooking your schedule, suggesting that you push tasks to tomorrow instead. And if you don’t find time to get to a task four days in a row, it moves the task to your Archive—suggesting that the task may not be a core priority.

As for deeper AI integration, Sunsama is currently testing an AI-powered voice and text assistant to plan your day over a call or add tasks via SMS.

It’s a Pomodoro timer, journal, and habit-tracking app, too. You can start your day with what Sunsama calls a “ritual” to plan and jot down thoughts. Then, when it’s time for you to wrap up, the app logs the day’s work and recommends that you journal the day’s highlights.

With a full schedule of tasks planned out each morning, it would be easy to disappear into work, clearing out tasks one after another. That nearly happened to me—until a gong rang out in the background and Sunsama’s Pomodoro timer popped up, suggesting that I take a break. The app did the same thing when it was time for me to switch focus to another task, as well as when it was time for me to finish up for the day, offering another journal space for me to reflect on how the day went.

Sunsama pushes you to focus on what’s important, with recurring tasks—good for routine work tasks as well as personal things you should do, such as exercising and reading—and “objectives” to keep your largest goals in mind as you plan each day’s agenda.

Instead of acting as an autopilot, it’s a copilot for your schedule, providing step-away-from-the-grind reminders that create a thoughtful balance between focused productivity and staying aware of the time.

It’s privacy-focused. Sunsama’s AI features are powered by an “open-source AI model hosted securely in our cloud environment,” according to Sunsama’s privacy policy, which adds that “[your] data is processed privately and is never used to train external systems.”

Additionally, all data in Sunsama is encrypted in transit and at rest, and it is not shared with third parties who don’t already have access to it.

Flaws but not dealbreakers

• It takes time to learn. Sunsama requires fewer clicks to set up than competing tools, but its vocabulary requires acclimation. Sunsama organizes tasks into “channels,” what other apps call projects. You can group channels into “contexts,” creating a relationship between a project and a sub-project. It doesn’t, however, offer task prioritization, which seemed like a miss to me after I used the competing Motion and Reclaim AI apps to schedule tasks based on priority. Instead, Sunsama lets you tie tasks to “objectives” to focus on work that moves your goals forward. None of this is too difficult to grasp, but it does require changing how you think about tasks.
• Automation doesn’t work on mobile. Sunsama’s mobile apps (Android, iOS) are well designed but do not include full integration with external apps or task-scheduling support. Whereas the desktop apps show, say, your full Todoist inbox, the mobile app shows only the Todoist tasks you’ve already scheduled in Sunsama. (To schedule a new Todoist task on the go, you have to copy it from the Todoist app and then paste it into Sunsama). Automatically scheduling tasks into your next available slot is, similarly, a desktop-only feature. The mobile app does offer AI features to file tasks into channels and estimate their duration, though.
• The app lacks a meeting scheduler. Sunsama’s core focus is your personal work; it doesn’t provide any team-focused, collaborative features. As such, it lacks a Calendly-style scheduling tool, which is a feature that many competing apps offer. You won’t find any tools to view schedules in multiple time zones, either. However, since Google Calendar now includes a built-in tool to share your availability and book meetings, Sunsama’s omissions are less of a downside than they might otherwise seem.
• It’s expensive. At $20 per month at this writing, Sunsama costs four times as much as Todoist and is double the price of a subscription to Microsoft 365’s Office suite. It does more than Todoist, but the value proposition makes sense only if you juggle complex schedules across multiple calendars and project-management tools and commit the time daily to plan and then review your work.

AI task-scheduling apps still offer a lot to like. With many of the apps we tested, you could ignore the headline AI features and still get value from the ability to organize tasks from all your apps, schedule them alongside events in your calendar, and let other people book meetings without overbooking your schedule. Those features—not AI—are the core reason to use task-scheduling software today.

They can show you a unified task inbox

Most of the apps we tested can sync tasks from popular work software, including project-management apps like Todoist and Asana, developer-focused tools like Jira and GitHub, notes apps like Notion and Obsidian, and team-chat software like Slack and Microsoft Teams.

Commonly, they also can turn messages from your email inbox into tasks and work with automation software such as Zapier and IFTTT to create tasks from their extensive libraries of integrations. Even the most limited apps show tasks alongside your calendar.

With that bird’s-eye view of everything you need to do—or, at least everything you’ve logged in an app—you’re less likely to overbook your schedule or forget a critical task.

You could build something similar in any to-do list app manually, by reviewing every app in your portfolio each morning and then adding your commitments to the day’s itinerary. Or you could build automations to copy new tasks into your primary to-do list app for you. But having a unified view of all your tasks synced across apps is valuable. If the software you use is supported, that alone could be a reason to use one of these tools, regardless of its AI features.

However, you would still have to manually add tasks from unsupported software or from one-off requests in tools like Google Docs or Figma where comments require work but aren’t a task per se.

They can schedule tasks on your calendar

AI scheduling—often paired with automatic task categorization and time estimation—is the headline feature for this category. The apps’ landing pages typically mention that AI will schedule your tasks but tend not to share much in the way of details. In every app we tried, we had to search around to find how to get tasks automatically scheduled on the calendar. Typically, we discovered, it works in one of two ways:

Fill in the gaps: In this approach, the AI adds tasks to your calendar in any available time slot, ordering them by priority and scheduling around your standard work hours and existing meetings. Such apps also may reschedule tasks when tasks run over time, when overlapping meetings are scheduled, or if you don’t get to a task within the day. That’s how Sunsama, Motion, Reclaim AI, and other apps work, each with slight differences in their auto-rescheduling. Motion also includes a tool to clear out your day’s schedule, moving everything to the next available slot, and lets you block hours to keep the AI from scheduling tasks during your focus time.

Timebox tasks: In some other apps, you first break the day into timeboxed segments; perhaps your morning is for admin tasks, while your afternoon is for focused work. The AI then fills relevant tasks into the times automatically. That’s how Morgen and Akiflow manage your work, with Morgen automating the scheduling and Akiflow handling the categorization.

The best results come when you add more data to tasks. If you set the priority, detail your sub-tasks, and categorize work, the AI is more likely to schedule tasks in a way that will make your work flow together. For the most part, when the apps we tested supported task priority, they would consistently schedule a higher-priority task before one with a lower priority. And with timebox apps, you have to categorize tasks before the app will automatically add them to a relevant timebox.

They can sync tasks and events between calendars

Every AI task-scheduling app shows your to-do list and calendar together and blocks time on your calendar when you’re scheduled to work on a task. Typically they also let you sync multiple calendar accounts to see, for instance, your work Outlook calendar and your personal Google Calendar events in a unified view.

You can then check your agenda on the go from your calendar app. You’ll also avoid situations where people book meetings on your calendar for times when you’ve planned a focused-work session.

Reclaim AI and Morgen can sync events between your work and personal calendars, with options for you to obscure task or event names. That feature allows you to keep your personal time blocked out on your work calendar without sharing exactly what you’re doing.

That’s another core feature that could make this category of apps worth considering. Again, you could approximate something similar by setting up automations to add each new event from one calendar to another. You can also do this natively in Google Calendar and other calendar apps, with separate calendars for personal and work tasks that combine into a unified agenda. Having your calendars automatically synced, though, is a cheat code for people who juggle multiple calendar ecosystems.

They can allow other people to book time on your calendar

Another common feature—available in Akiflow, Morgen, Motion, and Reclaim AI but not in our top pick, Sunsama—is a Calendly-style meeting-scheduling tool with a link where other people can book meetings in openings on your schedule. Instead of emailing to ask someone if they can meet you at 3 p.m. today or 10:30 a.m. tomorrow, for example, you share your meeting-scheduling link and let them pick the open slot in your schedule that works better for them.

Google Calendar includes a similar built-in tool, as does the aforementioned Calendly and other competing apps. Booking links are a nice bonus if you’re already using an AI task-scheduling tool, but they’re not enough reason to switch to such an app on their own.

If you really want AI to schedule your meetings: Consider using ChatGPT, Claude, or any other chat-based LLM directly. While testing the task-scheduling apps, I stumbled upon this approach as an easier way to attain the same core functionality that most of the contenders provided, at minimal cost.

First, I copied and pasted existing events from my calendar and wrote out everything I needed to accomplish that day. I didn’t tell Claude how long I thought each task would take, but I did ask it to group similar tasks, and I did mention when a task needed to be completed before another. Seconds later, Claude gave me a detailed plan for the day, complete with reasonably good time estimates and longer tasks automatically broken into segments to fit around meetings.

I then updated the plan throughout the day, adding new tasks and meetings as needed, and Claude rearranged my schedule to fit everything in. It even turned the agenda into a CSV file that I could import into a to-do list app.

It’s a manual process, sure, but it also turned out to be a smarter AI scheduling workflow than most AI task-scheduling software offers. And it’s a glimpse of the future that makes it difficult for us to offer clear recommendations of AI-specific features today.

Reclaim AI, acquired by Dropbox in August 2024, offers the best value of any of the apps we tested—it’s the only one with a free plan that includes AI scheduling. It’s free for individuals and reasonably priced for teams, starting at $10 per month per user at this writing. It schedules tasks around existing events based on the prioritization you add to tasks, and it splits larger tasks into smaller chunks of time to fit them in. It can also sync events between work and personal calendars, which is helpful if you’d like to avoid having people book meetings when you’re focused on work. Reclaim AI took less time to set up than other tools, and its meeting-booking tool—something that typically requires at least a few clicks in other apps—required zero additional setup. However, it works only on the web and offers no native desktop or mobile apps. In some ways, it comes across like a simpler, more corporate-friendly take on Sunsama.

Morgen automatically schedules tasks based on timeblocks. After you categorize tasks and add categorized timeblocks to your day, Morgen’s AI slots them in. It can import tasks from other apps, it includes a Calendly-style tool to book meetings, and it has a workflow tool to sync events between calendars or add buffers between tasks. Its AI scheduling feature isn’t available on mobile, though, and it lacks Sunsama’s review tools for more introspection about your day.

Motion automatically schedules tasks around gaps in your workday, based on task priority, and it does that well. It reorders your schedule if you change a task’s priority or when meetings are added to your calendar, too. We liked its timezone feature, which allows you to see the time in two places on your calendar, as well as its tool to clear out your schedule for the day. But it was one of the most expensive apps we tested—$29 per month at this writing—and it took far more clicks to set up than the competition.

Structured is a well-designed to-do list app, with GPT-powered chat for planning projects, adding tasks, and scheduling personal work. Its AI chat tool does far more than those in other apps: It can selectively move tasks around (“clear out my schedule other than the airport pickup today,” for example) or schedule tasks based on existing ones (“book time to send emails before I head to the airport”). But we found that such power carries with it the ability to quickly mess up your schedule, as you can’t undo changes once they’re accepted. Structured offers fewer features and integrations than the competition, and it works only on Apple and Android devices, but even in its incomplete state it offers a glimpse at what smarter AI may bring to project management in the future.

Akiflow provides a universal inbox that can schedule tasks from a variety of apps onto your calendar. It uses AI to categorize tasks (it added an “Email accountant” task to a finance project in my tests), but it does not automatically schedule tasks on your calendar. Instead, it offers daily rituals for you to plan work, produces notifications before you’re scheduled to start a task, and gives you a keyboard-driven interface to keep you focused on work. Its website hints at more GPT-powered features in the offing, though. It was also the most expensive app we tested, at $34 per month.

Trevor AI is built around Todoist, which (for now) does not include its own scheduling AI. Its user interface requires more steps than competing tools to complete similar tasks, though, and it doesn’t automatically reschedule times if you have overlapping commitments.

Day Flow is an iPhone-and-Android-only, chat-powered to-do list app. It can add tasks to your personal to-do list via voice or dictation, but it can’t import tasks from apps other than Apple Reminders, nor can it automatically schedule tasks already in your to-do list.

Antispace is task management turned into a game, complete with AI-generated avatars and a backstory for your character. It too lets you chat with AI to add tasks and plan your day, but it has no integrations to manage tasks across multiple apps.

This article was edited by Ben Keough and Erica Ogg.

1. Neha Kirpalani, Harvard Business Review writer about productivity and timeboxing, LinkedIn interview, February 27, 2025

2. Marc Zao-Sanders, Filtered.com founder and author of Timeboxing: The Power of Doing One Thing at a Time, email interview, February 6, 2025

3. Nancy Colter, instructor of Emory University’s “Managing Your Time and Productivity” course, email interview, February 14, 2025

4. Kashmir Hill, writer, The New York Times, email interview, February 12, 2025