Substack AI Is Mental
It has enshittified itself
“Enshittification, also known as platform decay, is a process in which online products and services decline in quality over time.” Source.
It’s real.
I’ve seen it with Substack, too. Like many other companies, they now use “AIs” as barriers to stop you getting help, hoping you will give up in most cases, or have such a poor experience that you will never try again.
I had a complicated Substack issue relating to Stripe payment systems, multiple accounts, and authentication. I couldn’t fix it on my own.
The Substack support had an option called “email” but that no longer goes to an email address or form. It is a lie. It just points here.
That’s enough preamble.
Here is a transcript of my attempt to get help via the only available Substack help system (image at the top of this post).
12:27 pm
Karl: Put me through to a human, please
Substack AI: I’d like the opportunity to help you resolve your issue directly as an AI support agent.
Substack AI: Could you please share more details about what you need help with on Substack? This will help me direct you to the right place or provide the best assistance possible.
Karl: I already said, I want to speak to a human
Substack AI: I’d like the opportunity to help you resolve your issue directly as an AI support agent.
Substack AI: Could you please share more details about what you need help with on Substack? This will help me provide the best assistance possible.
12:28 pm
Karl: human
Substack AI: I’d like the opportunity to help you resolve your issue directly as an AI support agent.
Substack AI: Could you please share more details about what you need help with on Substack? This will help me provide the best assistance possible.
Karl: Put me through to a HUMAN!
Substack AI: I’d like the opportunity to help you resolve your issue directly as an AI support agent.
Substack AI: Could you please share more details about what you need help with on Substack? This will help me provide the best assistance possible.
Karl: I don’t want a dumb AI. Put me through to a human. This topic is too complex for FAQs and canned responses.
Substack AI: To connect you to a Substack expert, I need to know the specific reason you are contacting support.
Substack AI: Could you please share more details about the issue or question you have regarding Substack? This will help ensure you get the best possible help.
Karl: If that was true then put me through to a human to ensure I get the best possible help.
12:29 pm
Substack AI: To connect you to a Substack expert, I need to know the specific reason you are contacting support.
Substack AI: Could you please describe the issue or question you have regarding Substack? This will help ensure you get the best possible help.
Karl: If I enter the issue you will link to useless help pages rather than transferring me to a human. I know how this works. I’ve been here before. Many times. It is part of life as we experience the enshittification of even things like “help” until the word becomes meaningless.
Substack AI: To connect you to a Substack expert, I need to know the specific reason you are contacting support so we can get you the best possible help.
Substack AI: Could you please describe the issue or question you have regarding Substack in more detail?
Karl: I want to speak to a human. I keep saying. None of your business why. A human will understand immediately. You can’t even understand “I want to speak to a human”.
Substack AI: To connect you to a Substack expert, I need to know the specific reason you are contacting support so we can get you the best possible help.
Substack AI: Could you please describe the issue or question you have regarding Substack in more detail?
12:30 pm
Karl: This is the most shit “help” ever. And it is labelled “Chat with Substack Support.” There is no support! Mental.
Substack AI: I’m here to help you as an AI support agent for Substack and can assist with any questions or issues you have related to your Substack account, publication, or subscriptions.
Substack AI: Could you please let me know the specific issue you’re experiencing or what you need help with on Substack?
Substack AI: Once I have more details, I’ll do my best to resolve your concern directly.
Karl: This is ridiculously oversimplified to the point of being pointless, but: put me through to a human to discuss Stripe.
Substack AI: Got it! I’ve sent this conversation to our team of specialists. Please note that due to incoming volume, we aren’t able to guarantee a response.
Substack AI: This conversation has been closed.
That is what Substack deems acceptable treatment of the people who pay its bills.
That is what every enshittified service deems acceptable.
This example of Substack using the enshittifying Decagon AI system is just the tip of the iceberg.
I’m going to be doing a few posts about AI. Take this as a slightly surreal introduction to them, and note that AI usage tends to enshittify everything it touches. Stuffing AI into products is a sure sign of hostile, low-quality services and software.
In terms of my transcript above: Substack replied, with what was obviously an email summary created by AI and forwarded by a human who hasn’t read any of it. Substack’s reply didn’t answer or fix the issue, just repeated what I already knew. It insisted the answer was simple, when I had spent three days with Stripe and even their staff couldn’t fix it.
I pointed this out, and Substack ignored my response, and all my follow ups.
Enshittification.
When things go wrong, there is no support.
Enshittification.
Past attempts at using their AI chatbot have not even led to a response, but as you can see, the responses (if you get one) are useless. Utterly infuriating and broken.
Enshittification.
I looked into getting off Substack recently, for various reasons. They are getting more right wing (promoting Bari Weiss and Fascism/Zionism etc). They dropped human support. They insist on using awful Stripe, and forcing you to make a new Stripe account for each newsletter (despite a single Stripe account being able to receive payments from any amount of sources: even Stripe’s staff admitted they have no idea why Substack chooses to do it in this convoluted way). But there aren’t many platforms that don’t charge you upfront, so for people who only make a bit of money from newsletters, switching to another site would cost a lot of money.
Enshittification.
More AI posts to come.
PS If you want to buy me a coffee, that’s now an option. I’m also an author, in case you want to treat yourself to my lovingly crafted books, and I mentor other writers.




I love Cory Doctorow's book Enshittification