Debugging Toggl Time Tracking Glitches for Freelancers

Debugging Toggl Time Tracking Glitches for Freelancers

ByUS Stacked

1. Creating a Toggl project that matches how humans actually work

This is the first thing I screwed up. When I started using Toggl, I set up projects like they’re folders: one for each client. Easy. “Client A,” “Client B.” Boom. Except that doesn’t work when you split a day across four types of work for the same client. My design billables are not the same as my post-launch maintenance, but they all funnel into “Client A.” And then I’d forget what task I was even timing because the descriptions blurred together.

The fix: separate projects by activity type instead. So now I have projects like “Design Work,” “Bug Fixes,” and “Client Admin” — and tags for which client it was. Counterintuitive, but it makes reports readable. Now I can group by tag to see total hours per client, or group by project to see how I’m spending my brain.

Also: delete default workspace. Mine was sitting there sucking in random entries from old Zaps without me realizing. Wasted two weeks billing to “Default Project” before a client asked me where the report was.

2. Automating Toggl start and stop using Keyboard Maestro on macOS

You’d think the Toggl desktop app could handle smart behavior like auto-starting when I open Figma or Notion. Nope. It’s dumb. Looks nice, but dumb. So I chained it up with Keyboard Maestro.

Here’s the stack:

  1. When I open Figma, KM triggers a Toggl AppleScript to start a timer with “Design Work” project.
  2. When I close the window or switch apps for 10+ minutes, KM stops the timer automatically.
  3. Slack idle status also acts as a secondary trigger if I’m inactive too long (via a shell script pinging the API).

Toggl’s AppleScript dictionary is limited, but the critical command is:

tell application "Toggl Track"
  start new time entry with properties {description:"Figma session", project name:"Design Work"}
end tell

Don’t ask how many times I ran that and nothing happened. Turns out: if the Toggl app is open but not in focus at least once, AppleScript silently fails. Found that via Console.app logs after 45 minutes of thinking my syntax was broken.

3. Zapier workflow for logging Toggl entries automatically into Notion

This was my Monday night rabbit hole. I needed a Notion database that logged all Toggl time entries per week, grouped by project and by day. Using the Toggl Zapier integration directly is fine until you try to do splits across dates or adjust summaries — the toggl-to-notion integration flattens hierarchy.

What works:

  • Zap trigger: New time entry in Toggl
  • Formatter step: Convert start time to date string (e.g. Monday)
  • Filter: Ignore entries shorter than 3 minutes (accidental misfires)
  • Action: Create Notion page in “Time Log” database with project name, duration, and notes

What doesn’t: updating existing pages. Each entry creates its own line. If I pause/start a timer twice in a day for the same project, I get two logs. Aggregating into a single row requires either Make, or you hold Zapier hostage with a Notion Search step and some janky conditional logic. Even then, Notion sometimes just drops the traffic — I got a 429 via webhook that wasn’t documentated on the Zapier end at all.

4. Inconsistent Toggl rounding behavior when exporting weekly reports

You ever bill a client for 10 hours, feel weird because Toggl says 9:58, export the report, and it rounds to 10.1? That number’s not even consistent.

Spent an entire morning frustrated because I thought I was underreporting — turns out: export rounding is based on the display format setting at the time you generate the report. If you’ve been toggling between HH:MM and decimal (see what I did there?), it’ll round differently each time. But Toggl never shows you the exact source minutes in that screen. Only way to get consistent data was dumping the raw export as JSON and parsing myself.

Also found this line buried in a response JSON:

{“roundedUp”:true,”durationInSeconds”:359}

That ‘roundedUp’ flag only appears if you request decimal output via the reporting API — it’s NOT available from the dashboard export. One of those things where the API is safer than the GUI.

5. Unexpected resets when switching between mobile and desktop Toggl apps

Was commuting and toggled a timer via the Android app, then got to my laptop and opened Toggl Desktop. Timer gone. Not stopped — gone. No history of it. It showed up two hours later in the browser with a timestamp five hours in the past.

Turns out the mobile app caches entries locally until sync. If battery saver is on or you have spotty signal, it might delay pushing to the cloud. Then, when you open desktop, the sync conflict defaults to the more recent login. You lose the mobile one entirely unless you do a forced refresh on desktop, which is hidden under File → Sync Now.

Shouldn’t be this fragile, but it is. Since then I’ve added a backup IFTTT Zap that logs all started timers to Google Sheets immediately. It uses phone OS triggers rather than Toggl ones, which is a weird workaround — basically, every time I open the Toggl app on Android, it writes a row with timestamp. Not elegant, but it saved me from an embarrassing timesheet gap last Thursday.

6. Using Toggl tags to trigger branching behavior in Make workflows

Got obsessed with this for a week. If I tag an entry with “deep” or “shallow,” I can branch that into completely different logging behaviors — like logging “deep” work to Slack every 25 minutes, Pomodoro-style, and discarding “shallow” entries under 10 minutes.

Make (the former Integromat) has a Toggl module that lets you watch time entries and pull tag arrays. But — here’s the glitch — if the entry uses a default tag added by the mobile app, the tag comes across as null in the webhook. Only way to get it consistently is to manually re-save the entry in web view. Not documented anywhere.

This snippet from a Make log helped me catch it:

“tags”: null,
“duration”: 783,
“description”: “Email Cleanup”

Once I started forcing tag edits via the desktop app, webhook payloads stabilized, and I could branch workflows again. One branch posts time blocks to an accountability Discord. Another adds “deep” entries to a separate Notion DB for later reflection. Ridiculous? Yeah. But it works, and made me spot that half my afternoons vanish into shallow-tagged Slack wanderings.

7. Combining calendar events and Toggl data to identify missing logs

This one stung. Client pointed out I hadn’t logged a 2-hour client call last Thursday. I swore it was on the calendar. It was. But with no Toggl entry, I had no invoiceable item. So, I rigged a cross-check that highlights gaps.

How it works

  • Google Calendar API pulls events with a specific label: “billable”
  • Toggl reports API pulls time entries by date range and project name
  • Compare entries by timestamp overlap (within 10 mins)
  • Any calendar event without a matching Toggl log = warning email with subject line: “MISSING LOG?”

Ran into a stupid timezone issue. Calendar exports as RFC3339 UTC, but Toggl sends local time in browser interface. They overlap visually, but offset by 5 hours if you just compare raw data.

Once I added a moment.js format conversion with explicit timezone declaration in the middleware script, it clicked. Now I get a daily email with bold red text if there’s a 15+ minute calendar event logged with no matching Toggl time. Last week caught three gaps that would have cost me like an hour of billables total.

8. Renaming Toggl descriptions in bulk using their unofficial API

This is off-books. I don’t recommend it unless you’re desperate — which I was, after realizing half my entries had the client initials instead of full names and weren’t showing up in filtered reports.

There’s no bulk rename function in the GUI. But the API docs mention a PUT request to /time_entries/{id}. Couple that with a cURL loop and you’ve basically got what you need.

curl -v -u "api_token:api_token" \
  -X PUT "https://api.track.toggl.com/api/v8/time_entries/$id" \
  -H "Content-Type: application/json" \
  -d '{"time_entry":{"description":"Fixed Description"}}'

Ran into 429 rate limiting when updating more than 50 entries in a few seconds. Knocked it down with a 500ms delay between cURL calls and wrapped it in a bash loop run overnight. Felt dirty. But it worked.

Note: if the entry was running (active), Toggl rejects the PUT silently — no error, just no change. Logs said 200 OK but nothing updated. Entry has to be stopped before edit. That missing error message wasted a whole debugging session till I spotted it via a test entry I knew I’d stopped.