A to-do app with file attachments on every task

Plenty of tasks come with paper. “Renew the passport” needs a photo that meets the rules and a form you printed once. “Tokyo: three days” needs the ryokan confirmation, the itinerary a friend sent, and the packing list you reuse every trip.

Without a place for them on the task, the files scatter: a downloads folder, an email thread, a photo somewhere in the camera roll. The task says what to do, and the thing you need to do it is three searches away, usually at the moment you have the least time, at a check-in desk or on the phone with someone.

Open a task and its files are a row of square tiles under the notes and the checklist. A picture shows a thumbnail. Anything else shows its type, so a PDF, a Markdown file and a text file are told apart at a glance. The name and the size sit under each tile.

A task holds up to 20 files. In a list, a paperclip after the title tells you which tasks have them, next to the icons for notes and checklists.

In the web app, a task with no files has an “Add attachment” button next to “Add checklist”. Once a task has files, the last tile in the row adds more. You can also drag files from your desktop onto the open task, and you can add files while you write a new task, before it is saved.

Each file uploads with its own progress bar, and a cancel button stops it. Pick five files at once and they go up side by side. If one fails, it stays as a red tile that says why, with a Retry when a second try can help, so the others aren’t held up by it.

The app checks a file before it uploads: its type, its size, and the room left on your plan. The server checks all of it again, and reads the first bytes of the file, so a file renamed to look like a picture is turned away.

Click a picture and it opens in a viewer over the task, with the other pictures of the task in a strip below it. The arrow keys move between them, and Download keeps a copy.

A text or Markdown file opens in the app too. Markdown is shown formatted, with its headings and lists, and a switch shows the plain text. A text file saved in an older Windows encoding still reads correctly.

A PDF opens in a new browser tab, where the browser’s own viewer shows it. Word, Excel, PowerPoint, Pages, Numbers, Keynote, OpenDocument, RTF, CSV and ZIP files download, and so do HEIC photos, which most browsers can’t show. Nothing is edited in place: change the file on your computer and attach the new version.

Files are on every plan. The plans differ in how big a file can be and how much you can keep in total:

• Free: 10 MB a file and 100 MB in total. That is a lot of PDFs and phone photos, and not many scans at full resolution.
• Premium: 100 MB a file and 5 GB in total. The 5 GB is a hard cap on the lifetime plan too, because storage keeps costing money after a one-time payment.

Settings → Storage shows how much you use, how many files you have, and how much of it sits in the Trash. Every file is in one list, largest first or newest first, with a download button and a remove button, so you can clean up without hunting through tasks.

A removed file comes back with Undo, and the files of a task in the Trash count until you empty the Trash. If you stop paying, nothing is deleted: every file stays and opens, and new uploads wait until you are under the free limit again. The same rule covers projects and areas on the free plan.

The iPhone app shows the same files in the task, and “Add attachment” opens a menu with three sources: the photo library, the camera, and Files, which reaches iCloud Drive and the file providers of other apps. Photos taken in the iPhone’s HEIC format are converted to JPEG on the way, so they preview on the web too.

Tap a picture for a full-screen viewer that swipes between the task’s pictures. A text or Markdown file opens as plain text, a PDF opens in an in-app browser, and anything else opens in the share sheet, where Quick Look previews Office files and Save to Files keeps a copy. A long press on a tile offers Share and Remove.

Two things are different on the phone. The rest of the iPhone app works offline, but files don’t: adding or opening one needs a connection. And the iPhone has no storage screen; use Settings → Storage on the web for that.

Files are stored in a private bucket. Nothing in it is public, and nobody can list it. The app gets a link to a file when it needs one, and the link stops working after a few minutes, so a link copied from your browser doesn’t keep working for anyone else. Picture thumbnails are made on the server, so the original never has to load just to show a tile.

The JSON export lists every file with its name, type and size, but it doesn’t contain the files themselves. Download the ones you want from Settings → Storage. Deleting your account deletes every file with it. The privacy policy has the details.

Most task apps take files in some form, and the differences are in where a file goes and what the free plan allows. The table states only what each vendor documents.

Todoist takes more kinds of file than TaskPocket, video included, and documents no cap on the total. Its files go on comments, one per comment, so a task with five files has five comments. If you keep video with your tasks, Todoist or TickTick fits better. TickTick also takes voice recordings, and its free plan counts uploads: one a day. More in TaskPocket vs Todoist and the TickTick alternative page.

Apple Reminders can hold photos and scanned documents, and it scans paper with the camera straight into a reminder, which TaskPocket can’t. Things 3 doesn’t attach files to a to-do: a file shared from the Finder becomes a link to where it sits on that Mac. The full comparison is in TaskPocket vs Things 3.