Your Claude Pro limits are based on the total length of your conversation, combined with the number of messages you send.
In order to get the most value out of Claude Pro:
Start a new conversation via the “AI” icon in the top left corner when you want to discuss a new topic. Claude needs to re-read the entire conversation every time you send a message, so starting a new conversation will limit the amount of work Claude needs to do to continue the conversation. Bonus: Claude will also respond faster to shorter conversations.
Ask multiple questions at once, especially if you are asking Claude questions about a long document. Because Claude needs to re-read the conversation each time you send a new message, asking questions in individual messages would use up your limit faster than a single message with multiple questions in it.
Don’t re-upload files. Claude sees the entire context from your conversation, so you don’t need to upload the same file multiple times (unless you start a new conversation).