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Outlook Calendar Sync

Think different. Sync different.

Synchronize a selection of your Outlook work appointments to your personal iCloud calendar.

(for Windows)
Last update: 29.03.2025

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Features

Main Use Case

As a busy professional managing both work and personal commitments, keeping track of your work schedule outside the office can be challenging. You might prefer using your personal iPhone over a company phone for convenience, or perhaps you don't have a work phone at all. However, company policies often restrict the use of personal devices for work purposes, making it difficult to stay updated with your work calendar.

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Introducing Outlook Calendar Sync - the perfect solution for employees who use Microsoft Outlook but can't sync their work calendars to their personal iPhones due to company restrictions. With Outlook Calendar Sync, you can seamlessly transfer your Outlook appointments to your personal iCloud calendar via the Outlook Desktop application.

As a long-time employee of large companies with many regulations myself, I understand the importance of maintaining both your privacy and adherence to company policies. My tool only syncs the titles and locations of your work appointments, ensuring your data remains secure. Now, you can effortlessly manage your work-life balance by staying updated with your work schedule on your personal device without compromising privacy or violating company rules.

Comparison

Stay on top of your appointments, whether you're at home or on the go, and easily hide your work calendar as separate iCloud calendar when you need personal time. Outlook Calendar Sync helps you keep your professional and personal lives in perfect harmony.

Free Trial

Try it for free for 14 days. No login or credit card required.

Flexible Configuration

Settings user interface, configuration file, blacklists, regular expressions.

Works in Background

Simply does its job in the background, no need to keep it open.

Privacy by Default

Data is handled securely and privately by design. All settings are privacy-oriented by default.

Detailed list of features


  • Seamless Outlook to iCloud Calendar Sync: Effortlessly synchronize Outlook calendar events to an iCloud calendar with one-way, filtered syncing.
  • Privacy-Focused Configuration: Default settings prioritize privacy by design.
  • Non-Intrusive Syncing: Sync seamlessly into an existing iCloud calendar without affecting current entries, whether the calendar is empty or already populated.
  • Flexible Configuration Options: Easily customize settings through the SyncSettings.json file (auto-reload feature) or a user-friendly configuration interface.
  • Selective Event Filtering: Ignore specific events using customizable blacklists with regular expressions.
  • Event Title Transformation: Apply regular expression transformation patterns to event titles through the configuration file.
  • Automation Support: Utilize command line arguments for automation (type /? for more information).
  • Automatic Startup: Enable automatic start through the Windows Task Scheduler, with the startup folder as a fallback option.
  • Localization: The user interface is available in the following languages: German, English, French, Spanish, Japanese and Simplified Chinese.
  • Wide Compatibility: Compatible with all supported versions of Windows 10 and above, tested on 64-bit Intel/ARM systems, and works with classic Outlook Desktop 2019+ with the COM interface.
  • Easy Real-Time Log Review: Review the log stream in real-time when the console window is displayed.
  • Full-featured trial version: Test the application without restrictions for 14 days without the need to sign-up.
  • Free version: Use the application with restrictions for free and forever.

A note on Data Privacy


Because I do not collect any data from the program, I am unable to see if you experience any issues while using it. I kindly ask that you appreciate this commitment to high privacy standards at a low, fixed price (with no recurring subscription fees). Instead of posting complaints publicly, please provide your feedback directly by submitting an issue on the GitHub page linked below. If you're unable to do so, feel free to send it via email.

About Me

Professionally Pragmatic.

With a university degree in computer science and over 20 years of experience in the software industry, I currently work as a Senior Software Architect at a large German company. I am passionate about software development and actively advocate for privacy by design and default settings. My expertise lies in developing and designing cloud-based services, ensuring that data protection is a top priority in all aspects of my work.

In addition to my professional work, I am also a passionate software developer in my personal life. I enjoy creating tools and utilities that are helpful in daily life. "Outlook Calendar Sync" is one such tool I developed to improve my work-life balance. I hope it can be of use to you as well.

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Pricing

Pricing Plans

Currently, there is only a lifetime license available for Outlook Calendar Sync. The price is a one-time payment and it includes all future updates within the same major version of the product. I'm planning to add an option for a monthly subscription in the future.

POPULAR

PERSONAL

€ 14.99*
(lifetime licence)

  • One user
  • Up to 5 Devices
  • 14-day unlimited trial
  • Lifetime license
  • Full-featured
  • Free updates
  

FREE

€ 0.00

  • One user
  • 14-day unlimited trial
  • Then limited features
  • Free updates

*) Including VAT. The price may vary depending on your location.

After the trial period ends, you will be prompted to purchase a license. If you choose not to purchase a license, the program will switch to the free version with limited functionality. Currently, this means that it will only sync the current day's and the next day's appointments. The lifetime license includes all future security and feature updates for the same major version of the product.

Payment is possible with credit card or PayPal, in many cases even in your local currency. You will receive an invoice with VAT included by email. You can use this to deduct the expenses from your taxes.

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FAQ

Any Questions? Answered.

I will include the most frequently asked questions here.

Download the Outlook Calendar Sync installer to your Windows desktop and run the installation program. Once installed, open the program from the start menu. You will be prompted to enter your iCloud credentials and select the iCloud calendar you want to sync to. Customize the other settings according to your preferences and click on the "Save" button. The calendar synchronization will begin immediately.
The synchronization is one-way, meaning that appointments are only synced from Outlook to iCloud and not the other way around. Only the appointment subject (title) and location are synced according to the configured settings. No other data, such as attachments or detailed descriptions, is included to prioritize privacy. The synchronization process runs in the background and does not require the program to be open. Any changes made to appointments in the target iCloud calendar will not be reflected back to the source Outlook calendar and will be overwritten during the next synchronization.
After installing the program, the trial period will begin automatically. No sign-up or credit card information is required during the trial. Once the trial period ends, you will be prompted to purchase a license. You can easily complete the payment transaction within the application.
Currently, only a personal license is available. Each employee of your company would need to purchase their own personal license. I'm planning to introduce a business license option in the future.
Currently, the application is only compatible with the classic Outlook Desktop application. I'm planning to add support for the new Outlook soon. Until then, it is also possible to install both the classic and the new Outlook apps in parallel and to perform synchronization with the classic app. Microsoft is planning to replace the classic Outlook with the new Outlook starting 2025. According to latest information the classic Outlook Desktop application will be supported at least until 2026.
The application has been extensively tested and is designed to work on all officially supported versions of Windows (10/11+) and Windows Server (2019+) in all editions on x64/ARM-based systems. It is compatible with Outlook Desktop (classic) versions 2016/2019/2021/365. However, please note that the application is currently not yet compatible with the new Outlook app for Windows or the web-based version of Outlook and is not able to use the Microsoft Graph API directly. I'm working on that now, the plan is to support the new Outlook app way before the classic Outlook Desktop app is discontinued.

To alleviate your employer's security and privacy concerns, it is important to highlight that the app's installation strictly adheres to privacy settings, ensuring that no information is unintentionally shared outside the company. The selected calendar data is also directly transferred between the local Outlook calendar and your personal iCloud calendar via an encrypted HTTPS connection.

Furthermore, the company could save a significant amount of money by eliminating the need for company-provided smartphones for a large number of employees who actually only require access to their schedules, even when working remotely. A smartphone may not be essential for their job responsibilities.

Testimonials

What our Customers Say

Here are some testimonials from satisfied users -
translated for better readability.

"At first, I thought this approach would be too limited since there are tools out there that perform complete bidirectional calendar sync, including details and attachments. But this is brilliant—there are many situations where this is an absolute advantage."

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Amélie Dupont

Project Manager

"Even though the program doesn't yet support the new Outlook app, I was able to use it easily by installing the classic Outlook app in parallel. It automatically uses the classic app in the background, and I still only use the new Outlook app."

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Linda Moore

IT Specialist

"With this tool, I don't have to worry about my kids messing up my work calendar when they play with my personal phone. ;-) The one-way sync is exactly what I wanted. My work calendar should be the only place where I manage my planning. I hate it to deal with bidirectional sync issues."

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Helga Prinz

Product Manager

"Since I started syncing important meetings from my work calendar with my wife’s personal iCloud calendar, our evening and weekend planning has been so much smoother."

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David Wilson

Team Leader

"I'm working on a voluntary project alongside my job, and the people there need to know when I’m busy or free at work to coordinate accordingly. This tool lets me share exactly the relevant information from my work calendar with them, without any privacy concerns."

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Michael Johnson

Volunteer Coordinator

"This was the missing piece in tool support for managing a good work-life balance!"

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Greg D.

Manager R&D

"I don’t want to pay for it, but even the free version, which syncs for today and tomorrow, is valuable to me. I sync my appointments to our family calendar so everyone knows when I’m coming home today, and it helps us plan for tomorrow together."

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Carlos García

Finance Analyst

"I like it! It perfectly solves my problem. I’d love it even more if it had an option to sync into both an iCloud and a Google calendar in the same sync!"

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张伟 (Zhāng Wěi)

Data Analyst

"I asked my IT administrator if it was okay to use a tool like this. He was skeptical at first, but after taking a look, he said it should be absolutely fine. The tool doesn’t do anything critical and seems to be very well designed with data protection in mind."

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Kevin Brown

Developer

"At first glance, I wondered what regular expressions were and why I should know about them. Sounded like techie stuff. But this is brilliant. It allows you to fine-tune the sync to your very specific needs and is still easy enough to use for simpler tasks."

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Jessica White

Business Analyst

"Sometimes I need to make my planning available to different people. I use the tool to sync some meetings to a dedicated iCloud calendar and then share that with those people. I can perfectly filter the appointments and limit the sync to exactly the right time period. It hit the nail on the head for me."

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Laura H.

Project Coordinator

"Now I can plan my public relations events in my normal Outlook calendar, and the tool syncs them to my publicly shared iCal automatically. Big time-saver!"

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Matthew Green

PR Specialist

"There’s a lot of room for additional features, but it’s a perfect starting point. I support it and am really looking forward to new features soon."

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艾丽 (Ài Lì)

Frequent Traveler

"I’m an event planner, and in my team, we use the tool to sync calendars of multiple people to a central iCloud calendar for a comprehensive view of all appointments and deadlines. Very helpful."

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Andrew Lee

Event Planner

"As a consultant, I work for multiple large companies where I have additional calendars to manage. Now I can sync all of them into one iCloud calendar and keep everything organized."

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Linda Müller

Consultant

"I always get into trouble with my family when I’m late for a flight. I’m a frequent traveler and very conscious of my personal family time. Now I can’t forget to share my flight appointments with my personal calendar—the tool reliably takes care of it."

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Mark Thompson

Frequent Traveler

"I’ve been looking for something like this for ages. It works flawlessly and keeps my personal and work life organized."

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Rachel D. Harris

Operations Manager

"Works well. I haven’t tried it yet, but it might even allow me to use Outlook Add-ins now with my iCloud calendar :-)"

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Just_me

Systems Engineer

"I’m a fan of the advanced recurrence features in Outlook. The tool supports them well, and I can now use them with my iCloud calendar!!"

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Anna Martinez

IT Consultant

"Unfortunately, this tool isn’t available for Outlook on macOS. I tried it on Windows, and it’s super! Please make it available for Mac as well."

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David König

Graphic Designer

"I’ve always wanted to regularly copy just the titles of my work appointments into my personal calendar, which I use as a sort of diary. This tool finally gives me that option in a very simple way, including a history of the past few months."

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Olivia Sánchez

Marketing Executive

CONTACT ME

Let's talk about Outlook Calendar Sync.
Love to hear from you!

My Location

Erlangen, Germany

Further questions?

support@thomas-gossler.de

Want to report a problem or submit a suggestion for improvement?