Either way, if the problem is the async nature of ICS,
shouldn't an alternate method be provided?

Try with the TransmitFile function
https://msdn.microsoft.com/en-us/library/windows/desktop/ms740565(v=vs.85).aspx

You may create a descendant of the THttpCli, override the SocketDataSent method and use the TransmitFile from there. Check the Indy IdStackWindows.pas for code (function ServeFile) that uses the TransmitFile.
If this work, maybe it can be integrated in the ICS code.
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