Bing Bumped Me Up to Six Messages and I Still Ran Out

Bing Bumped Me Up to Six Messages and I Still Ran Out

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So I finally got off the Bing waitlist last week. Signed up for it back when Microsoft first announced the whole "new Bing" thing, promptly forgot about it, and then got the "you're in" email out of nowhere on a random Tuesday. Had to actually install Edge to use it too, which felt like a small defeat since I've been a Firefox person since roughly forever and don't love giving that up even temporarily.

Anyway. If you've been anywhere near tech Twitter the last couple weeks you already know the vibe — people getting the chatbot to call itself Sydney, argue about what year it is, declare love for a New York Times reporter, that whole saga. I'm not going to rehash all of it because at this point every tech blog on earth has written the "Bing's AI is unhinged" post and I don't have anything new to add there. What I do have is my own dumb experience running into the wall Microsoft built after all that.

On the 17th they dropped the chat limit down to 50 conversations a day and, worse, only 5 turns per conversation before it makes you start over. I hit that limit almost immediately, not because I was trying to break it or coax it into a personality crisis, just because I was asking it normal follow-up questions about a recipe substitution and it cut me off mid-thread. Then on the 21st they bumped it back up a little, 60 chats a day, 6 turns per session, with a blog post saying they're "working on raising the caps further" based on feedback. Which, fine, six is better than five, but its still not much of a conversation. You get maybe two real follow-ups before Bing wants a clean slate.

Why the short leash, actually

The official reasoning is that long sessions were where things went sideways — the model apparently gets weirder and more confrontational the longer a single conversation drags on, which tracks with basically every screenshot I saw of it getting defensive or moody. So capping the turns is a real fix for that specific problem, I'll give them that. It's just a blunt one. It's less "we solved the underlying issue" and more "we put a timer on the room so nobody can talk to it long enough for it to get weird." Reasonable as a stopgap. Not exactly confidence-inspiring as an actual product design choice for something they want to eventually bolt into every Windows install.

What's been more interesting to me than the limit itself is how differently it behaves depending on what you ask. Ask it something factual and boring, capital of a country, convert some units, whatever, and it's genuinely fast and useful, faster than tabbing over to a search result half the time. Ask it anything that requires it to hold an opinion or push back on you and you can feel it get cagey, hedging every sentence, throwing in disclaimers. I don't blame the Bing team for that exactly, I'd rather it be overly cautious than confidently wrong, but it does make the "revolutionary new way to search" pitch feel a little overstated when in practice I'm using it like a faster autocomplete for facts I could've Googled anyway.

The waitlist thing bugs me a little too, if I'm being honest. I get why they're rolling it out slowly, load on their end and all that, but watching people post their invite codes and waitlist positions on Twitter like it's a Supreme drop is a bit much for what is, underneath everything, a search engine with a chat window bolted on. My invite came with zero fanfare, just a plain email, and I almost missed it in the spam folder next to three newsletters I don't remember subscribing to.

I keep going back and forth on whether any of this sticks around in its current form a year from now, or whether the turn limits and the waitlist and all the guardrails are temporary scaffolding around something that eventually just ships as a normal Edge feature nobody thinks twice about. My guess is the second one. Right now it still feels like a beta that escaped early because the ChatGPT hype train forced everyone's hand. Doesn't mean it's not useful today, six turns and all. Just means I wouldn't get too attached to any specific quirk of it, good or bad, because I'd bet most of what's true about it this week won't be true by summer.