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A user reports that the ReadFile call in console_get_userpass_input fails with ERROR_NOT_ENOUGH_MEMORY on Windows 7, and further reports that this problem only happens if you tell ReadFile to read more than 31366 bytes in a single call. That seems to be a thing that other people have found as well: I turned up a similar workaround in Ruby's Win32 support module, except that there it's for WriteConsole. So I'm reducing my arbitrary read size of 64K to 16K, which is well under that limit. This issue became noticeable in PuTTY as of the recent commit cd6bc14f0, which reworked console_get_userpass_input to use strbufs. Previously we were trying to read an amount proportional to the existing size of the buffer, so as to grow the buffer exponentially to save quadratic-time reallocation. That was OK in practice, since the initial read size was nice and small. But in principle, the same bug was present in that version of the code, just latent - if we'd ever been called on to read a _really large_ amount of data, then _eventually_ the input size parameter to ReadFile would have grown beyond that mysterious limit!