**Issue** Like @kapec94 in #2659, I came across confusing interaction between these parameters in Poetry (see [my comment on 9278](https://github.com/python-poetry/poetry/issues/9278#issuecomment-2108666111)). I think, now, that part of the problem I was seeing then was [Debian's python3-virtualenv](https://packages.debian.org/bookworm/python3-virtualenv), but I think I've compiled a list of problems using [this demonstration script](https://gist.github.com/hexmode/01c664dc51bbb5dd7bbbe10f2e0c3279) ([output](https://gist.github.com/hexmode/ba06b737b38a5e23def37a67cec0a819)). Interesting points: | ENV | python flag | try-first-with | activated | | notes | |-----|----------------------------------------------|-----------------------------------------------|-----------|----|-------------------------------------------------------------------| | | | ~/.asdf/installs/python/3.9.19/bin/python3.9 | 3.9.19 | ✅ | try-first-with is used and path is ignored | | | 3.9 | ~/.asdf/installs/python/3.9.19/bin/python3.9 | 3.9.19 | ✅ | try-first-with provides matching python | | | 3.9 | ~/.asdf/installs/python/3.11.9/bin/python3.11 | 3.9.2 | ✅ | try-first-with is ignored b/c wrong version, found python in path | | | ~/.asdf/installs/python/3.11.9/bin/python3.11| ~/.asdf/installs/python/3.9.19/bin/python3.9 | 3.9.19 | ❌ | python flag should be used (See [this comment on #2659](https://github.com/pypa/virtualenv/issues/2659#issuecomment-1779555809)) | | 3.9 | 3.11 | ~/.asdf/installs/python/3.11.9/bin/python3.11 | 3.9.2 | ❌ | python flag should override env (See [this comment on #2285](https://github.com/pypa/virtualenv/issues/2285#issuecomment-1013348779)) | Creating a new issue to focus the work.