Outlook Calendar Sync

Think different. Sync different.

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

This Windows desktop program synchronizes your (work) appointments from your Microsoft Outlook Desktop (classic) calendar selectively and one-way to your (personal) iCloud calendar with data protection and privacy in mind.

I created this program a long time ago and it's been doing a great job for me personally. Recently, I decided to make it available for others as well. I have polished it for being usable by a wider audience. I hope you find it useful, too.

And here's the typical use scenario for the tool (see also the homepage for a more detailed presentation):

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.

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.

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 😄

Let me know whether this fits your needs or if you have any suggestions for improvements.

Features

• Synchronizes Outlook calendar events to an iCloud calendar (one-way, filtered)
• Default configuration settings are privacy by default and design (see data privacy policy)
• Syncs reliably into an existing iCloud calendar (empty or not) without affecting existing entries
• Flexible configuration via SyncSettings.json (auto-reload) and/or config UI
• Selectively ignores events based on blacklists of regular expressions
• Configure regular expression transformation patterns for event titles in config file
• Supports command line arguments for automation (start with /? for more information)
• Support automatic start via Windows task scheduler (or startup folder as fallback)
• Should work on all supported Windows 10+ versions (tested on 64 bit Intel/ARM, classic Outlook Desktop 2019+ with COM interface)
• Allows to reviewing the log stream when the console window is shown

Usage tips

Many users might not be familiar with regular expressions, so here is a brief introduction:

In the settings fields where regular expressions are supported, you can easily exclude an event by using specific patterns. Here is an example to illustrate:

Example:

Suppose you want to ensure that events (i.e. Outlook appointments) with subjects (i.e. titles) containing the word "Lunch" are not getting synchronized. You would add the following line to the appropriate settings field:

Lunch

This pattern will match any title containing "Lunch" and exclude it from syncing.

If subjects shall only match when starting with "Lunch", you can use:

^Lunch

The ^ symbol indicates that the word "Lunch" must be at the beginning of the title to match.

"Lunch" at the end of a title would match with Lunch$.

An exact subject of "Lunch" would match with ^Lunch$.

Please note that these patterns are case-sensitive. To match both "Lunch" and "lunch," you have to use one the following ways to match in a case-insensitive manner:

^(L|l)unch

Important Aspects of .NET Regular Expressions

• Case Sensitivity: By default, .NET regular expressions are case-sensitive. To perform a case-insensitive match, you can use the (?i) option. For example, (?i)Lunch will match "Lunch," "lunch," "LUNCH," etc.

• Special Characters: Certain characters have special meanings in regular expressions (e.g., ., *, ?, +). To match these characters literally, you need to escape them with a backslash (\). For example, to match a period, use \..

For a deeper understanding of .NET regular expressions, you can refer to a comprehensive quick reference guide or search online for resources using terms like "Learn .NET regular expressions."

This online tool will help you to write and test .NET regular expressions.

By familiarizing yourself with these basics and critical aspects, you can effectively use regular expressions to manage your appointments and other tasks.

Download

You can find the latest version of the program on the Homepage or directly download it from here.

Roadmap

• Support the new Outlook app by directly using the Microsoft Graph
• Option to exclude appointments with certain Outlook categories or private flag
• Support multiple full sync target configurations in parallel
• Support more target calendar types than iCloud (e.g. Google calendar, Exchange)
• Introduce support for UI dark mode with update to .NET 9
• Configure a specific time period (start/end date) for sync instead of a floating time window (+/- 7 days)
• Option to sync appointments to different sync targets depending on their Outlook category
• Use the Windows Copilot Runtime to remove personal information from event titles before sync
• Further improvements based on feedback

Technology

• .NET 8 / C#
• WinForms
• iCloud.Dav.Calendar (.NET library for iCloud calendar access)
• Microsoft Azure Cloud (for hosting the backend service for licence handling)
• Paddle (for global payment processing)
• WebView2 (for enabling in-app purchase)