I cannot reproduce this on W10 even with incredibly low signal levels throughout.
The only way I can get a wobbly is to have a track or selection of pure silence and try to amplify that - for which I need to check the Allow clipping.
What I get then is the error message: Validation Error: Value Overflow
Now that may well be accurate - but it certainly isn’t very informative to your average user - I would expevct something like Can’t Amplify Silence.
If you can Export some small sample of your low signal level that fails with the error you report, as a WAV file anp post it here - then I can try testing that on my machines (I have a Macbook Pro as well for QA testing)
Possibly because you are using the current development code, or you just happen to have selected audio that has a peak level that rounds the right way.
This was a bug that appeared a couple of years ago due to improved input validation. It was fixed soon after it was noticed, but then broke again and no-one noticed until Peter spotted the problem last August. I fixed it again earlier this month (bug 963), so it will be fixed in the next release.