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Too little data for declared Content-Length #2064

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After a lot of debugging, I found out that it actually happens if I use the same BinaryIO Object multiple times. Is it the usual way? Can't we use it again if we need it without file.close() or with context manager? If no, mind giving a brief explanation why it works like that?

Okey dokes - let's see if we can make some user experience improvements here.

Can you provide an absolutely-minimal-as-possible example that replicates this, so we can talk it through? (You can use https://httpbin.org/post if you need a public URL for the purposes of demonstrating it)

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@ShivangKakkar
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@tomchristie
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