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Originally Posted by latepaul
Perhaps I wasn't clear that I wasn't necessarily waiting for the current "send" to complete before adding the next. Still not a problem?
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Shouldn't be. However, that doesn't say that it isn't.
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Not a Mac, a Linux PC. A couple of other things which may be relevant - I was getting other network activity whilst this was happening, specifically a notification from Draw Something. Secondly, immediately before the problem first occurred I'd done a Send to Device including a book that Calibre prompted me needing converting. I chose yes. I don't know if either of those could be part of the cause.
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Could be. We haven't seen the "MacOS problem" on any other system, but it could be there and you might be seeing it. That problem is that the OS signals "try again" sometimes on network writes when it shouldn't. It is worked-around in today's calibre release (0.8.65). Try that and see if the problem changes in some way.