The Obsidian-Apple Reminders Problem That Drove Me Crazy
Let me paint you a picture. You're deep in your Obsidian vault, capturing tasks with the excellent Tasks plugin. You've got due dates, priorities, recurrence rules—the whole system works beautifully. But then you're out walking the dog, and you remember something important. You ask Siri to add it to your reminders. Or you're glancing at your Apple Watch. Or checking the Reminders widget on your iPhone.
And there's the problem: two separate worlds that never talk to each other.
I lived with this cognitive dissonance for months. Maybe you have too. The Obsidian Tasks community has been asking for this integration since... well, since Apple Reminders got good. We've tried workarounds—exporting, importing, manual copying. They all suck. They break. They're not sustainable.
That's why when I stumbled upon Obsync on Reddit—a post that got nearly 700 upvotes and 92 comments of pure excitement—I knew something special was happening. Someone had finally built the bridge. And they made it free and open-source.
What Obsync Actually Does (And Why It's Different)
Obsync isn't just another sync tool. It's specifically designed for the Obsidian Tasks plugin ecosystem, which means it understands the nuances that generic sync solutions miss.
The core functionality is deceptively simple: two-way synchronization between Obsidian tasks and Apple Reminders. But the devil—and the magic—is in the details.
First, it handles due dates properly. Not just the date, but the time component too. If you have a task due at 3 PM in Obsidian, it shows up at 3 PM in Apple Reminders. This seems basic until you've tried other solutions that drop the time entirely.
Start dates work too. If you've scheduled a task to start on Friday in Obsidian, it won't clutter your Reminders list until Friday arrives. This is crucial for managing mental space.
Priorities map intelligently. Obsidian's priority levels (1-4) translate to Apple Reminders' flag system. Priority 1 becomes a flagged reminder. The mapping isn't perfect—Apple only has flagged or not flagged—but it's thoughtful.
Recurrence rules? Yep. If you've set a task to repeat every Monday in Obsidian, it'll create the appropriate recurrence pattern in Apple Reminders.
But here's the killer feature: completion writeback. Mark a task done in Apple Reminders (via Siri, your Watch, wherever), and Obsync checks it off in Obsidian. This is the true two-way sync we've been begging for.
Setting Up Obsync: The Practical Guide
Installation is straightforward, but there are a few gotchas you should know about. First, Obsync is macOS-only. If you're hoping for Windows or Linux support, you're out of luck—at least for now. The developer built it specifically for the macOS ecosystem, leveraging native Apple frameworks.
You'll download it from GitHub, drag it to your Applications folder, and launch it. It lives in your menu bar as a discrete icon. Right-click to access settings.
The configuration requires two main steps:
1. Point Obsync to your Obsidian vault. It needs to know where your markdown files live.
2. Grant it access to Apple Reminders. This happens through macOS's standard privacy permissions.
Here's what most tutorials don't tell you: Obsync works by scanning your markdown files for task blocks. It's looking for the specific syntax created by the Obsidian Tasks plugin. If you're not using that plugin, Obsync won't see your tasks. This isn't a limitation—it's by design. The developer built it specifically for that ecosystem.
Once configured, you can set sync intervals. I keep mine at 15 minutes. Some users prefer manual syncs. The menu bar icon shows sync status, which is a nice touch.
The Community's Burning Questions (Answered)
Reading through the original Reddit discussion, several concerns kept popping up. Let me address the big ones.
"Will this work with my existing Reminders lists?" Yes, but with a caveat. Obsync creates a dedicated "Obsidian" list in Apple Reminders. All synced tasks go there. This keeps things organized but means tasks won't automatically distribute to your existing lists. Some users wanted integration with their pre-existing grocery or work lists. That's not how it works—at least not in the current version.
"What about subtasks?" This was a common question. Apple Reminders supports subtasks (indented items). Obsidian Tasks doesn't have a formal subtask system, though some users create them with indentation. Obsync doesn't handle this mapping specifically. If you indent a task in Obsidian, it might not indent properly in Reminders. This is one area where the mental models differ between the two systems.
"Is my data safe?" Since Obsync is open-source, you can inspect the code. It runs locally on your Mac. Your tasks never hit a third-party server. The sync happens entirely on your machine between your Obsidian vault and your local Apple Reminders database. For privacy-conscious users (which describes most of the Obsidian community), this is huge.
"What about conflicts?" If you edit the same task in both places between syncs, Obsync uses a simple rule: the most recent edit wins. This works surprisingly well in practice, but power users might want more sophisticated conflict resolution. The developer has mentioned possibly adding conflict notifications in future versions.
Real-World Workflow: How I Use Obsync Daily
Let me walk you through my actual setup. This might give you ideas for your own system.
I keep all my project planning and detailed task management in Obsidian. Each project gets its own note with tasks embedded. I love being able to see tasks in context—right next to meeting notes, research, and documentation.
But when I'm away from my computer, I need quick access. That's where Apple Reminders shines. With Obsync, my carefully crafted Obsidian tasks appear on my iPhone without any extra work.
Here's a typical scenario: I'm in a meeting (in person, away from my laptop). Someone mentions a follow-up item. I pull out my phone and tell Siri, "Add to reminders: Email Sarah about the Q2 report." Siri adds it to my Obsidian list in Reminders. Later, when I'm back at my computer, Obsync has already synced that reminder into my Obsidian inbox note. I can then process it—assign it to a project, add details, set a proper due date.
The reverse flow works just as well. If I complete a task on my Apple Watch while commuting, it gets checked off in Obsidian by the time I sit down at my desk.
This bidirectional flow has eliminated so much friction. I'm no longer maintaining two separate task systems or doing manual transfers.
Limitations and Trade-Offs (Being Honest)
No tool is perfect, and Obsync has its limitations. Understanding these will help you decide if it's right for you.
First, it's macOS-only. If you use Obsidian on Windows but Reminders on iPhone, you're stuck. The developer has mentioned this is due to using native macOS frameworks. A cross-platform version would essentially be a complete rewrite.
Second, it only syncs with the Obsidian Tasks plugin format. If you're using another task system in Obsidian (like plain checkboxes or a different plugin), Obsync won't see them. This is intentional—the developer built it specifically for Tasks plugin users.
Third, there's no selective sync. It's all or nothing. You can't choose to sync only certain notes or folders. All tasks in all markdown files get synced. For users with massive vaults, this could mean a lot of tasks flowing into Reminders.
Fourth, custom metadata in Obsidian Tasks doesn't always map to Reminders. If you use custom fields like "estimation" or "energy," that data won't transfer. Apple Reminders has a fixed data model, so there's nowhere to put custom fields.
Finally, there's no web version of Apple Reminders sync. If you use iCloud.com to access Reminders, you'll see the synced tasks there, but that's it. No direct Obsidian web integration.
Are these dealbreakers? For most users, probably not. The core functionality works so well that these limitations feel minor. But it's good to know what you're getting into.
Alternatives I've Tried (And Why I Stuck with Obsync)
Before Obsync existed, I tried everything. Let me save you some time.
Manual export/import: Export tasks from Obsidian, convert to a format Reminders understands, import. This works once. Then it breaks. Maintaining it is a part-time job.
Shortcuts automation: Apple Shortcuts can do amazing things. I built a shortcut that would parse my Obsidian tasks and create reminders. It was fragile. It broke with updates. It couldn't handle two-way sync.
Third-party task managers: Tools like Todoist or Things 3 have better integration options. But then you're leaving Obsidian's native task system, which defeats the purpose. The whole point is keeping tasks in your notes.
Obsidian mobile apps: The official Obsidian mobile app is great, but it doesn't have Siri integration or Apple Watch complications. You can't tell your watch to complete an Obsidian task.
What makes Obsync different is its singular focus. It does one thing—sync Obsidian Tasks with Apple Reminders—and does it exceptionally well. It's not trying to be a general sync tool or support every possible workflow. That focus is its strength.
Pro Tips from the Community
After watching the Reddit discussion evolve and testing Obsync extensively, here are some pro tips you won't find in the official documentation:
Use a dedicated inbox note: Create a note called "Inbox" in Obsidian where all quick-captured tasks land. Tell Obsync to monitor this note specifically (though it monitors all notes). This gives you a clear processing workflow.
Leverage Siri location-based reminders: This is a game-changer. Since tasks sync to Apple Reminders, you can use Siri's location features. "Remind me to review the proposal when I get to the office" works perfectly. The reminder syncs back to Obsidian when completed.
Watch your battery: Obsync is lightweight, but if you set sync intervals too frequent (like every minute), you might notice battery impact. I found 15-30 minutes to be the sweet spot.
Backup before major changes: This is just good practice with any sync tool. Before making massive changes to your task system, ensure you have backups of both your Obsidian vault and Apple Reminders.
Use it with focus modes: In macOS and iOS, you can set focus modes to show only certain reminder lists. Create a focus mode for work that shows only your Obsidian work tasks. The integration here is seamless.
The Future of Obsidian-Apple Integration
Where could this go from here? The developer has been active in the Reddit thread, taking feedback and suggesting future directions.
Selective sync seems to be the most requested feature. Users want to choose which notes or folders get synced. This would help manage task overload in Apple Reminders.
Better subtask handling is another area. As both Obsidian Tasks and Apple Reminders evolve their subtask features, Obsync could bridge them more intelligently.
I'd love to see tags sync properly. Obsidian has a powerful tagging system. Apple Reminders has tags too (as of recent iOS versions). Mapping these could preserve more context.
But honestly? Even as-is, Obsync solves 90% of the pain points. It's that rare tool that feels complete on version 1.0.
Should You Try Obsync?
If you're a macOS user who lives in both Obsidian and Apple Reminders, absolutely. It's free. It's open-source. It solves a real problem elegantly.
The setup takes 10 minutes. The payoff is immediate. That cognitive load of maintaining two separate task systems? Gone. The frustration of not being able to capture tasks via Siri? Solved. The inability to check off tasks from your Apple Watch? Fixed.
Is it perfect? No. But it's remarkably good for a version 1.0 from a solo developer. And because it's open-source, the community can contribute improvements.
In my testing, it's been stable. It hasn't corrupted data. It hasn't crashed. It just works quietly in the background, bridging two worlds that should have been connected years ago.
The Obsidian community has been asking for this integration since the Tasks plugin first gained popularity. Now we have it. And it's free. Sometimes the best solutions come from someone scratching their own itch—and then generously sharing the scratch with everyone else.
Give it a try. You might just find, as I did, that it transforms how you think about task management across devices. No more compromises. No more workarounds. Just tasks where you need them, when you need them.
