Never Lose a Receipt Again With This Easy System! | Asana File Management

Aug 6

I was audited by the CRA in my first year of business, and I was not prepared.

Since then, I’ve learned my lesson—I now save every receipt right inside my Asana Income & Expenses Tracker.

If I ever get audited again (which, fingers crossed I don’t because it's still a lot of work), but if I did then I would be able to pull all my documentation in just a few clicks, and know exactly where to find everything.

No stress, no digging through emails.

If you've ever spent more time trying to find a file than actually working on it, I've been there too.

It used to drive me crazy—until I finally got smart about how I use attachments in Asana.

And today, I’m walking you through exactly how to upload, organize, and connect files to your tasks in a way that saves time, prevents chaos, and keeps your business super organized behind the scenes.

I’ll show you all the ways you can upload files—and I’ll share how I set things up so I always know exactly where to find what I need.

Either keep reading or watch the video below:

I’ve helped dozens of clients set up workspaces—and let me tell you, attachments are one of those little details that make a huge difference.

When they’re used well, you can find everything you need in a flash. When they’re not? It’s a total mess. So let’s fix that.

Why Attachments Actually Matter

I know attachments might not seem like the most exciting feature inside Asana, but hear me out—it makes such a difference for keeping things organized and easy to manage, especially when you’re juggling lots of moving pieces or working with a team.

Here’s why I love them:

They keep everything related to a task in one place—so you don't have to dig through email or Slack trying to find the file someone swears they sent.
They cut down on the back-and-forth and make feedback easier to manage.
And most importantly? They help you stay ready for anything—even an audit.

Like imagine this: Your designer uploads a few fresh logo options, your copywriter adds the draft sales page copy, and your VA includes a Tella video with your client’s feedback—all right there inside the same task.

That’s what I mean when I talk about having a central hub where everything lives.

Two Ways to Attach Files from Your Computer

Let’s start with the basics: how to actually add a file to a task from your computer.

There are two main ways to do this, and honestly, they’re both super easy:

Option 1: Browse for the file

Just click the little paperclip icon in the task, choose “From Computer,” and pick the file you want to attach.

Option 2: Drag and drop

If you’re a drag-and-drop kind of person like me, just grab the file from your desktop and drag it right into the task details pane.

Asana will take care of the rest. It uploads the file, saves it to the task, and logs it in the activity feed, too.

It’s these little wins that make such a big difference when you’ve got a lot going on.

Clipboard Magic (Copy + Paste)

Here’s a sneaky little trick that not everyone knows: you can actually copy and paste images or files right into a task description too.

Like, let’s say you just grabbed a screenshot of your analytics or your Stripe dashboard, or even a snippet from a PDF. Just hit Ctrl + C (or Command + C on Mac), go into the task’s description field, and paste it.

Asana will turn it into an attachment right then and there.

It’s perfect for quick feedback or saving reference materials that don’t need their own upload process.

Or if it just makes more sense to have it right there, in between your paragraphs.

Add Text + File in One Seamless Comment

One of the best features when giving feedback or leaving a note for your team? You can add a block of text and one or more files in the same comment.

This is especially handy when you’re reviewing designs, editing copy, or dropping a revised file in.

You don’t have to write a note, then upload the file in a second comment. Just do it all in one go—it keeps everything so much cleaner.

So, for example, you can leave a comment like “Hey! I updated the PDF based on our last chat—see attached. Let me know what you think!”

Simple, clear, and easy to follow.

Syncing Files from Google Drive, Dropbox & More

Now if you’re using cloud storage—like Google Drive, Dropbox, OneDrive, or Box—you can connect those directly to Asana, too.

Here’s why I personally love this:

I use Google Workspace, so my Drive is already organized with all my business docs. When I attach a file from Drive into Asana, I don’t have to download or re-upload anything. I just select the file, and it shows up instantly in the task.

Even better? If someone comments inside the Google Doc, Asana will notify me in the task. No more jumping between tabs or digging through email. It just shows up right where I need it.

File Size & Storage Limits

Here’s the lowdown on size limits:

You can upload any file from your computer as long as it’s under 100MB.
For larger files—like big video recordings or design files—just link them from Drive or Dropbox. Easy workaround!
There’s no limit to the number of files you can upload to a task. So if you’re anything like me and attach all the things… you’re good.

When Attachments Go Wrong (My Mistake = Your Lesson)

Okay… let me take you back to a moment I do not want to relive.

The first year of my business, I got audited by the CRA—and I had nothing in order. Receipts were in random folders, emails, and maybe even buried in a pile of paper on my desk.

I spent days trying to find everything and rebuild the trail. It was stressful, overwhelming, and it took way longer than it should’ve. Aaaand shocker - I couldn't find everything I needed to - which resulted in me owing money to the CRA.

Bummer. But it taught me a valuable lesson.

Now, the second I log an expense in my Income & Expenses Tracker in Asana, I attach the receipt right to the task. Every single one. I don’t even let myself move on until it’s done.

It takes two seconds—but it saves hours later. Future me is so grateful.

And it saves a ton of time during income tax season as well!

Track It & Stack It

And I actually made a full detailed workshop walking you through exactly how to set up the same kind of system.

It’s called Track It and Stack It—and it’s super affordable, super practical, and super satisfying once it’s done.

If you’re watching this thinking, “Okay wow, I need this setup ASAP,” check out Track It and Stack It here.

It walks you through building your Income & Expenses Tracker in Asana, step-by-step.

It’ll help you feel more calm, confident, and organized—especially around tax season.

Final Recap + Tips

Let’s wrap up with a few quick reminders:

Always group your files and feedback in one spot.
Use cloud storage for larger files and automatic version control.
Use the mobile app when you’re on the go (even if you’re hiding at the beach while your kid digs holes in the sand 😄).
And above all? Don’t leave future-you hanging. Organize your files now and thank yourself later.
Aaaand if you're ready to stop chasing receipts across your inbox, grab Track It and Stack It.