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It is hard to guess what might be happening without knowing much more about your configuration. That said ...
Have you entered and IP & port into CC? If so, and if this is required to work, then we can assume that something is a bit odd with your network. In particular, something is blocking CC's network broadcasts to find calibre. Whatever that "something" is might also be getting into the way.
Another possibility: CC will wait some 3 or 4 seconds for an answer from calibre. If the laptop is busy or must come out of a sleep or must be loaded from virtual memory then it might take longer than that for calibre to respond. If a connection fails, does another attempt also fail? If you bring calibre up to the foreground before attempting to connect, does it work?
Debug logs might help determine which component is seeing what. CC's debug logs probably extend far enough back to capture a failure, so if you send one to me (erase the multipie.co,uk address) I might be able to give more hints. Of course it might also say nothing of interest meaning I might need a calibre debug log as well, but we can cross that bridge when we come to it.
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