I don’t like Septembers (plural). When I was a boy, they reminded me that summers were over and it was time to get back to school. Later, they became a bitter reminder that I needed to start thinking about heating bills for our family home and the costs of a new school year for my daughter.

Now, Upwork has joined the Black September “party” with a new fee for something that used to be free:

“Direct to U.S. Bank withdrawals are free for freelancers with a United States tax address. Starting September 1, 2026, a $2.99 fee will apply to each Direct to U.S. Bank withdrawal if your tax address is outside of the United States.”

That’s me, and millions of fellow international freelancers on Upwork.

As (un)expected, Upwork freelancers expressed their frustration on Reddit because the good old Community was eliminated to minimize operational costs. Oh, how ironic and iconic, at the same time.

As you can see, there’s no conspiracy to silence the voices of revolt. It’s simple. There have been too many almost identical new threads about this new Upwork fee in the biggest sub on Reddit.

As you probably can’t see, there’s so much more here at play than just $2.99 to pay for each withdrawal.

There was one post on LinkedIn, which I can’t find, with a haunting closing line: “This is the last straw that broke the camel’s back.”

Is it? I had to go way back and dig deep into the history of Upwork fees. Fair and square, I don’t like to use AI when writing. This time, I really didn’t have a choice. As you will see for yourself, there have been so many changes and “introductions” that I wanted to make sure I’m not missing a thing (read: fees).

So, here you go, in all of its glory, because Upwork never said, here’s a new fee; we’re sorry:

Upwork Fees Evolution, Corporate Greed Problem With No Solution

It’s amazing, but not in a good way, that Upwork has left no stone unturned when it comes to monetization. This picture (table) is worth a billion dears to Upwork and a million tears to freelancers.

I should’ve called it a day right there, but I was furious and curious. Is there anything left to squeeze for extra profit on Upwork? I don’t want to be blamed for giving Upwork suits any new fee ideas, but it is what it is. ChatGPT came up with an idea for this table’s title.

Upwork: What Comes Next?

All of the following bad scenarios for Upwork freelancers are still hypothetical, but that doesn’t mean it’s impossible for them to become painfully real.

While we’re at it, why don’t you have a look at the performance of Upwork stock prices:

Upwork increased existing and introduced new fees when they were doing okay in the stock market. I can only imagine what’s going to happen now, when they’re in full business survivor mode. There’s some Upwork corporate dude asking ChatGPT, hey find me new ways to additionally charge freelancers.

This Story’s Post-Credit Scenes:

I had something different in mind as an illustration for my story.

Yes, my design “skills” are primitive. No, I’m not sure how many of my readers would recognize this Disney character. So, I asked ChatGPT for help. I have to admit that Upwork Gordon Gekko is awesome. Google Gemini also did a nice job:

Grok let me down. I’m not going to share the “result.” I used the identical prompt, just so you know, Elon Musk.

I would also like to express my gratitude to Sam Altman for the lovely tables. In the meantime, “Upwork integrated directly with ChatGPT, allowing users to find and hire vetted independent AI/ML professionals and draft job posts directly from chat conversations.”

Talking about the AI bubble and Upwork fees trouble.

I didn’t ask the Critical Drinker’s permission to use this picture. He didn’t ask Sony, so we will be fine. If you know, you know. Watch “Brand New Day,” skip “The Odyssey.” You don’t have to thank me later.