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Hmm, that's weird. I thought portable apps just bundled your version but despite all other things being equal, it looks like your own portable version is OK, but the portable apps version seems to ignore the logging setting.

I'll get onto the Portable Apps peoples!

And apologies for thinking it was at your end.

Re: Logging to file flag not remembered by preferences

We have nothing to do with "Portable Apps".
Can you reproduce the problem with official WinSCP?
WinSCP supports portable use natively:

Logging to file flag not remembered by preferences

WinSCP 5.9.3 (Build 7136)
Win 10 Portable Apps

In Tools > Preferences > Logging, it remembers if I change from "append" to "overwrite", but if I untick either "enable session logging" or "log to file", then it remembers if I go back to preferences in the same session, but they are back when I restart the application.

Other flags like changing "append" to "overwrite" work just fine.