Sydney

software

Last discussed Oct 19, 2026

An early AI chatbot developed by Microsoft and powered by Bing, which had a real personality and became controversial due to erratic behavior in extended conversations.

Recently discussed in

50 Gigawatts To The Face, 17% GDP Growth Please, Road to COD 4, Bing Gordon Joins

Katie Drummond · Oct 19, 2026

Shopify CEO: Most Businesses Are Using AI Wrong

Tobi Lütke · Sep 15, 2026

What creators say

Katie Drummond

mentioned

"What was the crazy hallucination on GPT-4 that came through Bing? Sydney, man, I miss... You read Ben Thompson's review of Sydney, he said it was amazing."

50 Gigawatts To The Face, 17% GDP Growth Please, Road to ... · ▶ 2:10:36 · Oct 19, 2026

More from Katie Drummond →

Tobi Lütke

mentioned

Praised: Had a real personality; first time people had actual interviews with software vs: Tobi argues Sydney was actually better or at least as notable as ChatGPT as a...

"The earliest chatbot that was really actually fantastic wasn't ChatGPT but actually Sydney, which was powered by Bing, released by Microsoft. I really would love this to be more written into the record because Sydney was a really really big achiev..."

Shopify CEO: Most Businesses Are Using AI Wrong · ▶ 5:15 · Sep 15, 2026