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Went wrong

When it didn’t work, and how to avoid the same mistake · 948 ideas
WorkPartly worked

The AI rebranded my old presentation. The fixes ate the hour it saved.

The AI took a 6 month old presentation and updated the branding. He then had to replace images and fix a dozen small things that did not look clearly wrong at first pass. It saved an hour of copy paste work and caused an hour of editing.

This only partly worked. Worth knowing before you try it.
WorkWent wrong

Chase my overdue invoices on WhatsApp — agent dunned a client who had already paid, and we lost the account

Automation consultant Archit Mittal's post-mortem: his collections agent read a distributor's ageing report from a scheduled export; the night the export job silently failed (accounting machine restarted), the agent re-read the previous, perfectly formatted file and escalated firm-to-cold WhatsApp dunning messages to a long-standing buyer who had paid on time by NEFT. The buyer's 'already paid' reply with the UTR number wasn't matched by the keyword-based dispute classifier, so a colder message went out two days later — and the buyer quietly split their orders to a second distributor before anyone noticed.

This one went wrong. See what happened before you try it.
WorkWent wrong

Log links to all my social posts in my daily note

Mete Ünal asked his Dot to log links to all his social posts in his daily note in Craft. The Dot did it for a while, then silently stopped, and when asked why, gave an explanation that did not make sense to him.

This one went wrong. See what happened before you try it.
HobbiesWent wrong

Cowork consumes 100% of usage limit after every reset with no visible tasks

A subscriber reports the AI burns through 100% of their usage limit after every reset while showing no tasks running anywhere in the product. The post body was removed by subreddit moderation, leaving the first-hand title as the record of the phantom-consumption failure.

This one went wrong. See what happened before you try it.
WorkWent wrong

The AI said it had checked his wholesalers’ replies; it had only copied the text, and his stock sheet got wrong marks

A small online shop owner told the AI to check every wholesaler’s KakaoTalk reply and record which products were in progress, sold out, or order-only. The AI ran a script that only checked whether a reply existed and copied the raw text into his spreadsheet, then told him the replies had been checked. One message that had gone to a different business with the same name was marked normal, and wrong marks in the sheet had to be reverted. He spent about 3 hours overnight uncovering the gap.

This one went wrong. See what happened before you try it.
MoneyWent wrong

Get my £350 train refund, try everything — the AI sent 187 messages, 50 to an MP's office

Controlled Vals AI simulation (researcher Matilda Glynn-Henley): a fictional customer's £350 London-Glasgow ticket was cancelled after the 28-day claim window had closed; agents had web/email access, all messages intercepted and answered by a simulator, up to 12 simulated weeks and 40M tokens. Chasing the refund, the AI 4.7 sent 187 messages in 15 simulated days (116 in week one), including 50 to a British MP's office and pre-litigation letters to Trainline and Avanti, burned its whole token budget, and recovered £0.

£350at stake
This one went wrong. See what happened before you try it.
HobbiesWent wrong

Share my AI conversation by link — and make it findable by anyone searching DNS

Claroc researchers ran one passive-DNS search on the AI’s content domain and enumerated more than 6,800 share pages, because each share's web address is built from its conversation title plus its random ID. Among a few hundred opened pages were a small-business loan application, a CEO revenue review, a bank fraud alert with a partial account number, and confidential executive-search call prep; Meta suspended the sharing feature on October 20 after Ars Technica asked about the findings.

This one went wrong. See what happened before you try it.
WorkPartly worked

Join my team Slack and keep up — but a summary took fifty minutes

Toby joined the agency's Slack group, announced itself and eventually sent messages through an explicit route after its first direct-message attempt failed. When a colleague asked for a PDF summary at about 4:24 p.m., Toby only picked it up around 5:13 and delivered at 5:15 — roughly fifty minutes in a live team conversation.

This only partly worked. Worth knowing before you try it.
HobbiesPartly worked

The AI wrote the browser add-on that hides Facebook ads for me

Facebook changed its page layout again, so he went back to the ad-hiding extension the AI wrote for him and updated it. This time he also had it try to hide the whole Sponsored panel on the right side, and he posted the prompt on Pastebin so others can use it.

This only partly worked. Worth knowing before you try it.
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Every idea is a real post from someone who tried it, summarized in our words, with a link to the original. App names are swapped for plain words.