Getting the Calendar Power Up Working
So here is what actually happened when I first tried to use the Trello Calendar Power Up for keeping deadlines straight. I enabled it, expected a magical calendar to appear, and nothing did. Or so I thought. The problem was that the little Calendar button doesn’t scream at you, it just sort of hangs out quietly in the top bar of your Trello board. I was staring at the cards thinking my dates would rearrange into a timeline. Nope. You need to click that Calendar view option at the top, otherwise nothing changes. Once you do, all your cards that actually have due dates suddenly lay themselves out across proper calendar days. It can be weirdly satisfying, like watching puzzle pieces fall into place 🙂
But here’s the catch — if you forgot to set a due date on a card (which is easily half my cards), it won’t show up at all. So the first step of actually making this useful is fixing your own bad habits. Every card that should have a deadline needs an actual date. Otherwise your calendar will look way too empty and you will think the tool is broken again.
Adding Due Dates Without Losing Your Mind
This is where things can get mildly annoying. If you make cards one by one and add dates straight after typing the card title, it works fine. But when you dump ten new cards quickly during a meeting, now you have ten cards with no dates. The fastest way to catch up is opening the card, clicking the due date button, and picking a date from the little popup calendar. Unfortunately there’s no bulk set option built into Trello’s base features. I checked twice hoping maybe they slipped something in for this, but nope.
One silly workaround I sometimes do involves exporting the board to a CSV, editing all the dates in a spreadsheet where you can drag down cells quickly, and then reimporting using another Power Up or automation app. But honestly that’s too much if you just have a handful to edit. Instead I just force myself to do the repetitive clicking because it is less risky than messing up my import. And yes, I have permanently misplaced cards by botching an import ¯\\_(ツ)_/¯.
Syncing Trello Calendar With Google Calendar
At some point, someone in your team is going to ask “can I just see these deadlines on my actual Google Calendar so I don’t forget?” And you can. The Power Up gives you an iCalendar feed link. You copy that link and subscribe to it in Google Calendar, Outlook, Apple Calendar, etc. I pasted mine into Google, waited a few seconds, and boom — all the Trello due dates appeared on the same screen where I keep meetings and personal stuff.
Here’s the catch though. It’s not instant sync. Sometimes I update a Trello date and Google Calendar doesn’t reflect that change for several hours. The first time this happened, I thought I messed something up, but turns out Google only refreshes calendar feeds on its own schedule (totally irregular). So if you change a bunch of due dates and then panic because they’re not showing up, just give it some time. If you are like me, you’ll also check the “Refresh” option three times even though it doesn’t guarantee anything.
Automating Deadline Reminders
Having due dates show on a calendar is nice, but if you actually want reminders, you need to tell Trello to send them. By default, Trello sends a notification about a day before a card is due. That’s sometimes fine, but I personally work better if I get a heads up maybe three days before. You can change this per card when setting the due date reminder. It’s a little dropdown where you pick “at time of due date,” “5 minutes before,” “1 day before,” etc. There is no custom option like “2 days” or “4 hours” unless you set up a heavier automation outside Trello.
I ended up building a Zap that looks for soon-to-be-due Trello cards and then posts messages into Slack. Of course, one week it worked perfectly, then next week it fired twice for each card. I had duplicate Slack messages and kept thinking I missed something. After logging into Zapier, I saw it had received duplicate webhook triggers from Trello. No clear reason why. Disabling, re-enabling, and reauthenticating the Power Up fixed it mysteriously. This is why I never really trust these things to run without me staring at them like a hawk :P.
Viewing Deadlines In Calendar Layout
The moment it clicked for me was dragging a Trello card directly across the calendar screen. If a task was on a Friday but I knew I needed more space, I just dragged it to next Monday. The date updated automatically inside the card. That felt so much faster than opening the card, clicking “Due Date,” and scrolling around in the little pop up. So if you are mostly adjusting deadlines for planning purposes, try living in the calendar layout instead of the list layout.
I sometimes keep one browser window open purely on the calendar view and another on the main board view. This way I can drag cards around like a timeline while still managing the checklist details. It’s not fancy but it honestly makes deadline shuffling way easier than trying to think in list form.
Displaying Multiple Boards Together
One frustration, especially if you manage multiple Trello boards, is that the Calendar Power Up only shows deadlines from that single board. I went digging for a master view thinking surely there had to be a way to see all boards in one calendar. Sadly, no. To get a combined view, you either subscribe each iCalendar feed into Google Calendar or pay for a bigger tool that sits on top of Trello.
I ended up adding the feeds from three separate boards into one Google Calendar. They each came in with different colors, so I could distinguish them easily. The only gotcha is you need to keep track of which iCalendar feed corresponds to which board. I labeled mine carefully, otherwise I’d move a card date and later wonder why it was still showing up wrong in Google.
Solving the Silent Breaks
Here’s the part that drives me crazy. Sometimes the Calendar Power Up is running, looks fine, and then suddenly it just stops pushing updates to the external feed. You open Google Calendar and see everything is a week behind. There is no big error message in Trello, no red warning icons. It just silently breaks. My fix when that happens is to disable the Calendar Power Up, wait a second, and re-enable it. Usually that regenerates the feed and then Google eventually starts pulling fresh data again. I keep one old system log note that literally shows “ICalendar feed endpoint 503 error” when I checked it — but that got buried in Trello’s backend and they never really explained it.
So if you’re wondering why your Google Calendar looks stuck in the past, don’t waste hours clicking refresh. Just assume something silently broke and toggle the Power Up off and back on. It feels dumb but it usually works.
Comparing With Other Tools
I did run a test using Asana’s built in calendar side by side. Asana shows all tasks in calendar mode instantly without needing a Power Up. It’s slicker in that sense. But because I already have so many boards and automations in Trello, I’m not migrating just for that. Trello with Calendar Power Up is a little more fragile but still workable if you know the quirks. If you want to read straight from the source, Trello’s main site at trello.com has the cleanest explanation of features available, though real issues like feed lag or sync failure are not really highlighted there.
If you like to fiddle, Trello’s Power Up gives you enough freedom to bend it around your habits. If you want something that “just works” out of the box without babysitting, the experience might frustrate you. I personally live with the imperfections because I like dragging cards around my little digital calendar as if I’m arranging fridge magnets 🙂