The 9 best AI scheduling assistants in 2025

Productivity starts with your calendar—but sometimes it ends there too. No one wants to reprioritize an entire week after an emergency, or play calendar Tetris to land a meeting with that busy lead sometime in the next two days. This is where an AI scheduling assistant can help: instead of working on your schedule, you can let AI calendar apps do it for you.

I've been playing around with all sorts of AI tools recently. For this article, I considered a couple dozen AI calendars and did in-depth research and testing to find the best AI scheduling assistants that can sort out the tricky bits for you.

Ready? Block a few minutes on your calendar, and let's dive in.

The best AI scheduling assistants

• Reclaim for protecting your habits

• Clockwise for syncing team calendars

• Motion for AI-assisted project management

• SkedPal for time-blocking

• Akiflow for integrations and a single task inbox

• Structured for planning with your voice

• Toki for managing your calendar via messaging apps

• Clara for having a virtual assistant in your email

• Kronologic for following up with more leads

Smart calendars vs. AI calendars

The best AI scheduling assistants help place your tasks on your calendar, reschedule conflicts, schedule 1:1s with ease, and group most of it into time blocks, so you do less context-switching. But should you move to a new app if you're already using a smart calendar or smart meeting scheduler? Here's a brief comparison to help you distinguish one from the other.

Smart calendars use deterministic algorithms—fixed rules built by developers—to make suggestions and optimize your calendar. It will always bring up the same results if you input similar data. For example: a developer may add a rule that says whenever a user adds a task called "jogging," schedule that task at that same time on every following day.

Calendar AI is more powerful because scheduling tools now connect to large language models (LLMs), passing your relevant event data along with specialized prompts. Based on this information, the model makes intelligent decisions about your schedule and sends recommendations back to the app. The app then takes action on your calendar—creating, editing, updating, or removing events and event details as needed. 

Some apps can track your preferences and usage patterns over time, using this data to refine how they schedule future events and plan your day. This creates a dynamic, personalized experience that adapts to your unique work habits and scheduling needs.

AI for scheduling: What to look for

Ready to go from smart to AI-powered? Here's what I looked for in every AI scheduling assistant I tested:

• Great user interface. You'll be looking at your schedule assistant app throughout the day—it's your calendar, after all—so it needs to be functional, intuitive, and easy to use.

• Easy to set up and offers a good set of integrations. It should take you less than five minutes to go through onboarding, which includes connecting your calendar of choice. I also prioritized apps that have integrations with other popular apps, so you can save time generating those Zoom meeting links, for example.

• More than a smart calendar. As I tested each scheduling assistant app, I was looking for true AI features. Where it was unclear if there was actual AI at work, I reached out to the support team to ask what kind of technology was running behind the scenes and learn more about the AI scheduling algorithms.

• Insights and tips. Each AI scheduler app listed here has tooltips, articles, and videos outlining how they work, so you can understand what's going on when your calendar is suddenly reorganized.

• Extras. I was looking for any innovative AI appointment scheduling features that could be game changers for the way you schedule and work through your day.

AI scheduling has two major subcategories. The first one is calendar management: everything about putting your tasks on your day, optimizing your schedule, and helping you move through it. The other is scheduling meetings: since booking time with others can be a puzzle of its own, AI steps in to handle the back and forth and lock in the slots.

Here's how I tested the apps you're about to read about: I signed up for each AI scheduling app and added my schedule, making some changes to see how the platform adapted as I did—the way it adapts shows if there's actually AI at work. I set up meetings with myself (via a bunch of separate calendar accounts) and rearranged events over the course of a week. I explored the settings, tried out all the available features, and watched the robots create my schedule for me. Based on all that experience researching and testing these tools, here are the best AI calendar apps.

The best AI scheduling assistants at a glance

Best AI scheduler for protecting your habits

Reclaim (Web)

Reclaim pros:

• Manages recurring events well

• Quickly reschedules and adjusts your calendar when it detects a conflict

Reclaim cons:

• No mobile apps yet

Strengthening habits is all about consistency, and Reclaim (now owned by Dropbox) is a great AI calendar assistant to help you build that consistency. It looks good, works even better, and it has the right balance between power and complexity.

The platform now supports both Google Calendar and Outlook Calendar (in beta). During onboarding, you set up your work hours, weave in your habits, and choose how Reclaim's AI Time Defense should prioritize your to-dos. You can set each habit to be Most flexible, Let Reclaim decide, or Most defensive. This means your morning workout can be rock-solid while your "learning time" can shift when urgent meetings pop up.

As you move through your day, all the action is on the Planner screen. It has a calendar view in the center with three lists on the right side: priority habits, open tasks, and low-priority habits. You can keep track of what's left to do with just a glance, great to keep your focus as you work.

You can enter all the tasks you have to tackle manually, and Reclaim will start dropping them on your schedule on its own. Better yet, you can integrate a wide range of task management apps and turn on sync, automating the whole process. As it populates your near future, it'll keep an eye out for deadlines, defending the time needed to complete critical tasks from an out-of-the-blue 1:1. Speaking of 1:1s, Reclaim empowers your weekly catch-ups by rescheduling any recurring meetings if someone has to cancel, finding the best time slot for both and sending the appropriate notifications.

If you're having a hard time sticking to your morning meditation or that brisk afternoon walk, Reclaim will get you back on track easily, without scheduling headaches.

Reclaim.ai price: Free plan available for 1 habit, 1 calendar sync, 1 scheduling link, 1 smart meeting, and 1-week scheduling range. Paid plans from $8/user/month.

Best scheduling AI tool for syncing team calendars

Clockwise (Web, Chrome and Firefox extensions)

Clockwise pros:

• Flags disruptive meetings in the calendar

• Plenty of in-app context and explanation

Clockwise cons:

• Can't be used with personal Google accounts, only Workspace

Clockwise's mission is simple: give teams back time by orchestrating everyone's calendars simultaneously. Its AI continuously moves flexible meetings, resolves conflicts, and "finds time where there is none." This way, everyone gets longer, uninterrupted focus time without sacrificing collaboration.

Clockwise has lots of knobs and levers. It's definitely the most customizable engine on this list, but now it's working at team scale. The onboarding experience (along with the Your ideal day settings you can revisit anytime) lets you fine-tune everything from working hours and meeting windows to lunch breaks and travel time. When teams set this up together, Clockwise creates and maintains real focus time blocks of 2+ hours by automatically shifting meetings to less disruptive slots.

When you propose a meeting, Clockwise calculates the "Focus Time cost" for every attendee and recommends times that minimize fragmentation across the entire team. It honors shared norms like no-meeting days, lunch breaks, and working hours, so the plan works for people and calendars. This is true for both internal and external meetings.

While Clockwise feels strong for solo players, it truly shines with teams. Connect it to Slack, and it updates everyone's status based on what's on their calendar, prevents non-urgent messages during focus time, and lets you schedule directly from internal comms. The effect compounds as more teammates adopt it: everyone protects each other's deep work time.

Unsure if it's actually doing anything for your team's productivity? The analytics dashboard shows organization-level metrics like focus time created, conflicts resolved, and total schedule assists, so leaders can see real impact and spot trends.

Clockwise price: Free plan available for basic features; paid plans from $6.75/user/month for advanced features, team productivity tools, and more security and support.

Best AI schedule assistant for project management

Motion (Web, Windows, Mac, iOS, Android)

Motion pros:

• It's becoming an AI-driven workspace

• Great task priority controls

Motion cons:

• A bit too complex

Motion started as a smart calendar with strong project management features. Over the years, it's grown to cover a lot more ground, including AI employees and a breadth of features that look to automate the work-about-the-work.

To be clear, all the good project management capabilities are still here. Clicking on the Projects & Tasks tab gives you a detailed breakdown of everything you and your team have to do, with ways to assign tasks based on roles. There's risk management for tasks, with labels that update as they degrade from being on track to at risk or even missing the deadline entirely. Your calendar and daily agenda updates are based on what you have to do, so you always have maximum clarity without digging into and working on your calendar manually.

So, how do the AI employees add to this core experience? Since there's a lot of productivity data stored on Motion, these AI agents use it to optimize schedules, take notes on your meetings, draft documents about your projects, and even document standard operating procedures to make sure everyone stays consistent.

There's definitely a learning curve in setting these up and understanding how they work. The payoff isn't instant, but compounds: the more you offload to these agents and they respond in the way they should, the more you can have peace of mind and forget the admin. Of course, be sure to test them thoroughly before relying on them.

With this AI infrastructure in place, you can connect even more data sources to Motion using the Zapier integration, offloading even more manual work to the machines by connecting Motion to thousands of other apps you use at work. Learn more about how to automate Motion, or try one of these pre-made workflows.

Motion price: From $29/month for all core AI features for projects, tasks, and calendars.

Best AI scheduling assistant for time-blocking

SkedPal (Web, iOS, Android)

SkedPal pros:

• Great onboarding

• Easy natural language input

SkedPal cons:

• Time blocking feature takes some getting used to

Time-blocking: the art of placing tasks on your schedule so you can actually do what you need to do. This is the main advantage, but there are others: you'll know how long each task takes, you can group up to-dos based on cognitive intensity or topic, and you'll have a more organized day in general. SkedPal is the best app to support you through this.

With a thorough and interactive onboarding track, you'll have all the skills you need to start using it in less than 20 minutes. The app has a collection of videos mixed with hands-on tutorials to help you interact with the app. You can add all the tasks you have to do: add the name and then the duration and due date in natural language. For example, if you write "Send outline 5m due Friday," the app will recognize that this task takes five minutes and you have until Friday to do it. Due dates are color-coded with the task, so you know if you need to pick up the pace with a glance.

The time-blocking feature takes a bit of getting used to because you have to set it up first—once you do it, it's a breeze to use. Click on your profile picture at the top right of the screen, and then click on Time Maps. SkedPal already separates your day into Mornings and Evenings—among others—so you can use those to funnel your tasks into time slots. But when you click Add, you can create a new time-blocking label and paint the appropriate calendar regions.

You'll notice you can paint in different colors: green slots will get filled up first, yellow will be next, and red ones are the last resort. This lets you customize how much the app will cram your tasks in a single day or push it out to the next week. To assign tasks to a time map, after you write the duration and due date in natural language, type a forward slash, and choose the one you want to lock it to.

If you want to get really into the nitty-gritty, you can set up time budgets as well. For example, I've decided to have five hours every week that I spend studying no-code development—whether that's in one sitting or one hour a day depends on what I have to do. SkedPal lets you create and keep track of these time budgets. So, in my example, I wouldn't accidentally schedule seven hours of studying, which would impact my productivity somewhere else. Time is a zero-sum game, so be sure to play it well.

SkedPal is the best AI scheduling assistant for time blocking—for people who want to group up their tasks by cognitive impact or topic, without having to meddle manually with the calendar. If meddling manually is an ick for you, connect SkedPal to Zapier and automate all the tasks around scheduling.

SkedPal price: From $9.95/month for core features and 1 connected calendar

Best AI calendar for integrations and single inbox

Akiflow (Web, Windows, Mac, iOS, Android)

Akiflow pros:

• Strong cross-platform sync and features

• Great at time-blocking and daily planning

Akiflow cons:

• Expensive; no free plan

With every productivity app producing an avalanche of data, it's really easy to turn a simple day into tracking a rocket launch operation. Dozens of dashboards, notifications, and entry points are a recipe for overwhelm, getting nothing done, and somehow feeling even more tired than if you did. Akiflow pipes all digital chatter into a single channel and lines everything up so you can bat it out of the park consistently.

The onboarding track personalizes the experience even before you register for an account. After you do, you can connect your calendar and move on to integrating other platforms such as Notion, Asana, and Slack. The more you bring in, the more you'll be able to see your entire day at a glance in a single place. From there, drag and drop what you need to do onto the calendar to block the time.

Whenever you add a new task, Akiflow's AI labels it automatically. This is good to understand what's personal, work-related, or pure boring admin. On top of that, you can browse each label on the left side and see all tasks grouped up, good to dump even more there, or see how far along (or not) you are in each area of your life.

The AI engine can manipulate your calendar based on your commands: on the bottom-right side, click to open the chat interface and command it to reschedule events, drop tasks on the calendar, or rearrange your day. It sometimes needs explicit controls, such as "look at my task list and place the overdue tasks on my calendar," to know where to look and where to take data to, but it's a minor obstacle.

Since Akiflow also has time-tracking with focusing features, it can deliver a daily report of how you're doing. You can see the hours you've worked and what you worked on in a simple pie chart, good to track where you're investing your time—and to explain why tasks from a certain project are disappearing fast while others sit untouched.

While the native integrations cover some of the biggest productivity apps on the market, the developer team hasn't had time to cover all the bases yet. But since Akiflow already connects to Zapier, you can connect your single inbox to thousands of other apps you use for work anyway. Get started with one of these templates.

Akiflow price: From $34/month for all features (there are also some flash sales)

Best AI calendar for planning with your voice

Structured (Web, iOS, Android, smartwatch)

Structured pros:

• Very easy task entry

• Smartwatch app available

Structured cons:

• Occasional sync issues

Wish you could talk it through to get a project planned and set on the calendar? With Structured, you can: open the mobile app, get to the AI tab, and talk your plans away.

The best thing about talking to AI is that you can ramble. Instead of having to organize everything inside your mind, typing it out, and organizing it on the schedule, you can talk everything out and let the machine sort it. Structured's engine will think for a bit and then lay out task suggestions that you can add one by one to your task list or all at once for convenience.

Beyond using your voice, you can use a prompt to start planning events or multiple tasks at the same time. For example, one of the suggested prompts is to plan a trip to Porto in Portugal. Instead of a response in free-flowing text, you also get a list of tasks that you can add to your list. These AI features only seem to be available on the mobile app: I couldn't find them on the web app, which is better for managing your calendar in-depth.

When placed on the calendar, Structured adds pauses and breathing room between events and tasks automatically. If you don't want those spaces, you can easily tap and drag to change the start times; for deeper editing, you can tap the task and then change the time, date, duration, or color.

The app is very geared towards personal use. The smooth user experience shows at every step. The wake-up time's graphic tops the day, with all your events lining up with cute and helpful icons to separate every event, task, and moment of your day. It all wraps up with your bedtime. If you want to stick to the schedule, all you have to do is take a look at the timeline.

Beyond calendars, Structured doesn't integrate with any major productivity apps in the space, so it's a bit of a data island. Still, the way it works makes it a nice central hub for all your personal tasks, with a nice side of AI-powered features to flesh out your days.

Structured price: Free plan includes most features; paid plans from $2.99/month, but prices might vary by region

Best AI scheduler for managing your calendar via messaging apps

Toki (WhatsApp, Telegram, Apple Messages, LINE, iOS)

Toki pros:

• Accepts multimodal inputs

• Call alert reminders for tasks available

Toki cons:

• Not available on Android nor as a web app

Using a new app always means a new browser tab you have to take care of, another interface to manage. Toki aims to reduce the burden by helping you manage your day straight from your messaging apps.

When you sign up, you can connect your preferred channels, such as WhatsApp, Apple Messages, or Telegram. This unlocks a new contact there that you can text and send commands to in order to change anything about your day. You can send commands to create an event ("schedule dinner for 7pm lasting for 2 hours"), change existing events ("let's move the event to 8pm"), or cancel it outright ("I can't do dinner after all, please cancel").

Toki accepts text messages, but you can also control it with your voice. You can speak your commands as voice notes, and it will parse them and translate them into the appropriate actions. It also accepts images as starting points, so you can upload a photo of a train ticket and it can add it to the schedule based on the information.

A unique feature here is how Toki can actually call you to alert you of tasks, just as a person would. You can set this up on a per-event basis. When the date and time come, you'll get a call from Toki so you can drop what you're doing and get on the task at hand.

The mobile app is very simple, offering a chat window where you can run the back and forth to manage your calendar as you go. When you tap on the bottom-left side icon, you can see your calendar at a glance, just to get a refresher or to make sure the changes you made carried forward. Everything is synced to your connected calendars, so you can view the event blocks in your calendar app of choice.

Toki price: Free plan available; from $10/month to increase scheduling allowances.

Best AI scheduling assistant for having a virtual assistant in your email

Clara (Web, via email inbox)

Clara pros:

• Advanced natural language processing handles complex scheduling intents

• Doesn't add an extra browser tab to your workflow

Clara cons:

• Still in beta

When it's time to meet anyone from your team or externally, so it begins: juggling meeting links, looking at your calendar, browsing theirs, and going through the click click click to reserve your slots. And if either you or they can't make it last minute, the dance begins again. Keep it in your inbox: Clara handles everything just by being cc'd on the conversation.

Before I dive into it, a quick filter: this app focuses exclusively on booking meetings with others, not on optimizing your schedule or getting your tasks on the calendar. You set it up the first time by setting your preferred meeting time boundaries (say, blocking your Saturdays and Sundays from any action at all), connecting your calendars and video conferencing, and you're ready to go.

The next time you're trading emails with anyone and you're ready to meet, simply cc Clara on the email thread (it has a dedicated email address) and state that you want to find a time to meet. It comes back to you almost instantly with up to five options based on open slots in your calendar. From this point on, everyone else on the email thread can send their availabilities or pick a slot in English, without having to click any booking link interfaces. You don't have to do anything else: once others pick the slot, it'll appear on your calendar, and video conferencing links will be rolled out automatically.

The previous Clara 2.0 relied on a mix of AI and humans-in-the-loop to make the magic happen. It would handle most of the scheduling automatically and hand off the more complex use cases to an internal team of human employees who would review and correctly schedule meetings based on the intent. The newer 3.0 version is fully powered by machine intelligence, with a custom engine that handles anything from an easy coffee meet to a 1-on-1 rescheduling marathon.

In addition to having tested and used Clara, I've worked on a couple projects with them, so I got a sneak peek at the behind-the-scenes and at the release calendar. Clara 3.0 is going through the finishing touches and is set to launch soon to a market that has no robust competitors in its class, especially after Gokatch is no longer available. Curious? If you're tired of booking links, join the waitlist and leave them behind.

Clara price: Not available yet

Best AI scheduling assistant for following up with leads

Kronologic (Web)

Kronologic pros:

• Automated meeting scheduling

• Can replace Calendly

Kronologic cons:

• Parts of the interface could be better

Kronologic is on a different plane when compared with the rest of the tools on this list. It's built to help sales teams schedule more calls with interested leads, increasing conversion rates across your sales pipeline. To fully explain what it does, I'll walk you through a few situations.

I've been testing software for a while. Most of it involves self-service registration, leading to a free trial or a free plan. But every now and then, there are a few apps that require filling out a form and waiting for a phone call to schedule a demo. And that's the beginning of the touchpoint roulette: Will they call me in five minutes? Two days from now? Will it take one phone call? Three? It's impossible to know.

After having a sales team from a CRM app call me at 2 a.m. in the cold British morning, I wish these apps would use Kronologic. Instead of filling the form and putting that lead on a queue, so a sales rep can pick it up whenever they can, the app automatically schedules a date and time when both parties are likely to be available. If the lead objects via email, Kronologic's natural language processing features will detect if there's a rescheduling intent and, if so, will update the invite to match. Sales team involvement during this process? If you want, zero.

This is the beginning of what Kronologic's AI engine can do. Let's imagine you've put together a list of 200 interested leads. It'd be great to schedule a call with them as soon as possible, right? But do you want to get your sales team in a frenzy trying to get hold of everyone?

Within the app, you can create the meeting type with the email template, and set the AI behavior to High-density scheduling. Emails will start going out to these leads, inviting them to a meeting at a specific time and date within a time period. Most of these meetings will overlap, but since the app keeps track of conversion rates over time, it knows your specific percentage. So even though you sent out 200 invites for 200 meetings in three days, not all of them are actually interested, so you can identify and get to talk to all the leads that are.

Kronologic price: From $112/user/month

How to find the best AI meeting scheduler

AI calendar management is the future—and I'm not sad about it. As I was researching each AI scheduling app, I started paying attention to how much time I spend on scheduling every day: it added up to about 45 minutes. That's 10% of my day (and maybe yours) spent on scheduling. 

If you're in the same boat—or in rougher waters—pick up the AI calendar app that speaks to your pain the most. Try it out for a few weeks and see if it helps you spend your time more productively. I'd be surprised if you didn't notice the difference after even a few days.

You can also try Zapier Agents, where you can build your own AI agents without any code. Train your agent to do things like meeting prep and follow-up tasks, or have it do a web search of everyone you're meeting with in a given day and create agendas for each one. Equipped with your live business data, Zapier Agents can manage your calendar even while you sleep. Learn more about how it works.

Related reading:

• The best AI productivity tools

• How to automatically manage your meetings with Zapier

• How to use Scheduling Assistant in Outlook

• The best AI email assistants

• Enterprise AI: How to leverage AI across your organization

• Make AI your new assistant

This article was originally published in August 2023. The most recent update was in September 2025.