If your AI assistant isn’t working, the most common causes are:
- context window overload (start a new conversation),
- unclear prompts (be specific about what you want),
- rate limits from your provider (wait 60 seconds and retry),
- or outdated API keys.
These 7 fixes in under 2 minutes.
Last Tuesday at 11pm, I was prepping a client proposal and my AI team member just… stopped. Mid-sentence.
I’ve built an entire company around AI delegation, LaunchLemonade, which helps hundreds of businesses hand off work to AI team members, so you’d think I’d be immune to this. I’m not. It happens to everyone. And after debugging hundreds of these issues across our platform, I’ve narrowed it down to 7 fixes that solve almost every case.
Here’s exactly what to check, in order.
Fix 1: Start a Fresh Conversation (Context Overload)
This is the #1 reason AI assistants stop responding.
Every AI model has a context window. What is it? Think of it as short-term memory. When a conversation gets too long, the model literally runs out of room to think.
How to tell: Your AI was working fine earlier in the conversation but gradually got worse, now with slower responses, less relevant answers, then silence.
The fix? Start a brand new conversation. Copy your most recent question and paste it fresh. Don’t try to continue a conversation that’s been going for 50+ messages.
Pro tip: If you’re using an AI team member for long tasks (like research or report writing), break the work into chunks. Give it one section at a time, not the entire project in a single thread.
Fix 2: Rewrite Your Prompt (Ambiguity Kills)
AI assistants are literal. If your prompt is vague, the model can get stuck trying to figure out what you actually want, especially with complex or multi-part requests.
How to tell: You asked something broad like “help me with my business” or gave conflicting instructions.
The fix: Be specific. Instead of “write me a proposal,” try: “Write a 500-word consulting proposal for a mid-size marketing agency. Include: scope of work, timeline, and pricing. Use a professional but warm tone.”
The structure that works every time:
- Role: “You are a [specific role]”
- Task: “Write/analyse/summarise [specific thing]”
- Context: “For [audience/purpose]”
- Constraints: “In [word count/format/tone]”
Fix 3: Check Your API Key and Rate Limits
If you’re using an AI tool through an API (like OpenAI, Anthropic, or through platforms like LaunchLemonade), your key might be expired, your account might be out of credits, or you’ve hit a rate limit.
How to tell: You’re getting error messages like “401 Unauthorized,” “429 Too Many Requests,” or the assistant just returns empty responses.
The fix:
- Log into your AI provider’s dashboard and check your API key status
- – Check your usage/billing page. Have you hit your spending limit?
- – If rate-limited, wait 60 seconds and try again
- – On LaunchLemonade, we can handle this automatically. Your AI team member switches between models if one is overloaded through Autorouting.
Fix 4: Clear Your Browser Cache
Sometimes the problem isn’t the AI, it’s your browser. Cached data, outdated cookies, or JavaScript conflicts can break the chat interface.
How to tell: The interface loads but messages don’t send, or you see a spinning loader that never finishes.
The fix:
- Hard refresh: Cmd+Shift+R (Mac) or Ctrl+Shift+R (Windows)
- 2. Clear browser cache for the last hour
- 3. Try an incognito/private window
- 4. Try a different browser
Fix 5: Check Your Internet Connection (Seriously)
I know this sounds obvious. But AI assistants need a stable connection to stream responses. A weak or intermittent connection can make it look like the AI died when it’s actually your WiFi.
How to tell: Other websites are also loading slowly. The AI starts responding but cuts out mid-sentence.
The fix: Test with fast.com. If your connection is flaky, switch to a wired connection or move closer to your router. If you’re on mobile data, switch to WiFi.
Fix 6: The Model Is Down (Check Status Pages)
AI providers have outages. More often than you’d think.
How to tell: Nothing you’ve tried works, and the tool was working fine yesterday.
The fix: Check the status page:
- OpenAI: status.openai.com
- – Anthropic: status.anthropic.com
- – Google AI: Check Google Cloud Status Dashboard
On LaunchLemonade, we connect to 21+ AI models. If one is down, your team member automatically routes to another. That’s the benefit of not being locked into a single model.
Fix 7: Your System Prompt Has Conflicting Instructions
If you’ve set up a custom AI assistant with a system prompt, conflicting instructions can cause the model to freeze or produce garbled output.
How to tell: The AI worked fine with the default settings but broke after you customized the system prompt.
The fix:
- Remove your custom system prompt temporarily. Does the AI work again?
- – If yes, add your instructions back one section at a time to find the conflict
- – Common conflicts: telling the AI to “always be brief” AND “provide comprehensive detail”
- – Keep system prompts under 500 words for best results
When Nothing Works: The Nuclear Option
If all 7 fixes fail:
- Create a completely new agent/assistant from scratch
- 2. Use a different AI model (if your tool supports it)
- 3. Contact support – the issue might be on the provider’s end
- 4. On LaunchLemonade, use the “Rebuild” button to reset your team member while keeping its training data
Frequently Asked Questions
Why does my AI assistant suddenly stop mid-conversation?
- The most common reason is context window overload. Every AI model has a maximum amount of text it can process in a single conversation. When you exceed this limit, the model stops responding or produces lower-quality output. Start a fresh conversation to fix this immediately.
Can my internet speed affect AI assistant performance?
- Yes. AI assistants stream responses from cloud servers, so a slow or unstable internet connection can cause timeouts, partial responses, or complete failures. You need at least a stable 5 Mbps connection for reliable AI assistant performance.
How do I know if the AI model itself is having an outage?
- Check the status page of your AI provider (OpenAI, Anthropic, Google, etc.). Most maintain real-time status dashboards. If you’re using a multi-model platform like LaunchLemonade, outages are less likely to affect you since traffic routes to available models automatically.
Why does my AI assistant give worse answers over time in the same conversation?
- This is called “context degradation.” As conversations grow longer, AI models lose track of earlier context and start producing less relevant responses. The fix is to start new conversations for new topics rather than continuing one endless thread.
Is there a maximum number of messages I can send to an AI assistant?
- While message limits vary by platform and subscription tier, modern AI models have moved far beyond the constraints of the past. Today’s flagship models feature massive context windows, and often ranging from 1 million to 10 million tokens, allowing them to process entire libraries of data without losing focus. While users may still encounter periodic ‘usage caps’ on free tiers, the historical issue of conversation quality degrading after 30 messages has been largely resolved through advanced context management and adaptive memory.
Your AI team member should work for you, not against you. If you’re tired of debugging AI tools, try LaunchLemonade – we handle the technical headaches so you don’t have to.
Create your first AI team member in 2 minutes: https://launchlemonade.app?utm_source=blog&utm_medium=organic&utm_campaign=ai-assistant-not-working-fix
Cien Solon is the founder and CEO of LaunchLemonade, building AI team members for every business. Follow her on LinkedIn for daily insights on AI, delegation, and building in public.
