Squeezer currently does take wrapping into account, i.e. it does take IDLE's "soft" line wrapping into account when counting lines. Therefore the auto-squeeze criterion of "at least X lines" does lead to auto-squeezing for any mixture of very long lines and/or many short lines.

However, there is currently a bug in the line counting mechanism which is causing it to not count long, soft-wrapped lines properly in some cases. This issue is about that bug, and the PR fixes it. Merging this fix should result in the originally intended behavior, which is similar to what Terry described in his last comment here.