Context loss. After roughly 10 messages, the conversation starts to drift. It loses the thread of what was established earlier, and you end up re-explaining context you already gave. For long-form projects or complex builds, this is a real productivity drain.
It agrees too much. This is the subtler problem. ChatGPT rarely pushes back. It validates, it elaborates, it expands, but it does not often stop you and say "that assumption is wrong" or "here is a better approach." A tool this powerful should have a stronger critical voice built in. One honest challenge is worth ten agreeable responses.
Version gaps in integrations. When building AI workflows with various tools, I noticed the software was not running the latest available version. That kind of lag creates friction when you are trying to build something current and reliable.
Claude by Anthropic