Why is Wine 9.0 not opening .exe files on my computer?

I have the same but PARTIAL problem you have.

I homebrew'd Wine 9.0 onto my 12.7 OS external, I am the Admin (was ROOT admin owner/etc BEFORE the bad move of upgrading the internal Mac Mini M1 to Sonoma, which permanently flaglocked the permissions and continues to infect new externals I buy even if not booting with the internal...). The drives didnt 'need the internet' to be validated and at no time did I ever agree knowingly to leave access to my own externals to APPLE to determine validation. It wasnt a problem before the 'upgrade'

As for the WINE problem, how did you install it? Compiled it from source, used homebrew, or a pkg app somewhere?

For me: It shows up as an app in applications, click it and it opens terminal, I get this series of fail/error results when I follow instruction to .exe the app in terminal:

Pic. #2

What SHOULD have helped both the external Thunderbolt enclosure SSD drive 'permissions block' Apple put on, and this problem of blocking emulator operation, was the following I tried.

I turned the Security drop down menu via Recovery OS to Partial from Full

then in Recovery still, typed in the csrutil disable command

I temporarily tried the Gatekeeper shut off command tho not likely part of the problem

Turned off the SIP 'protection'

Went in thru the system/library/coreservices folder chain into DIrectory Utility app found there, and reconfirmed the ROOT setting by entering my password after unlocking it.

None of that either changed the following Pic 2 errors nor ended the undesired Apple intrusion into my privacy choices. SECOND picture is the new 'you must have an internet connect to confirm the external' nonsense that they alone apparently get to decide is accessibility to my externals.

I would hate to think that backup/erase/reinstall any OS or data only drive is the way to get around this nonsense.

I suspect this Apple Gets To Choose Validation/permissions thing stops such terminal usage or installs they dont like.

if any of the above works for anyone, or anyone wants to pitch in some terminal command or Recovery OS steps I could try, maybe we both can run WINE and also have less hassled external drives.

The barebones WINE is not enough when used on an M-series Mac. WINE is meant to work with Intel/AMD CPUs. There are some add-ons which can allow WINE to work with an M-series Mac, but I don't think they've been included into the main WINE release yet. AFAIK, only CodeWeavers' CrossOver Mac is the only full fledged solution out of the box. If you want to use WINE, then you will need to try to install some third party add-ons which some others have packaged. Unfortunately I don't recall those items or where they can be downloaded. AFAIK, CodeWeavers has not sent those extra patches to the main WINE community yet (at least when I had researched thi some months ago).

Check out the CodeWeavers' forums & blog where you may find some more information about the extra items CodeWeavers had to develop to make WINE work on M-series Macs. IIRC, there were links to GitHub repositories where some of these items may be found, but keep in mind they may not be easy to install & configure. If you search this forum, then you may find my other post where I provided some links to these items & issues (sometime in the past year).

Keep in mind, that even fewer Windows apps will function in WINE on an M-series Mac than if they were used on an Intel Mac.

Here is the product page for CrossOver Mac:

https://www.codeweavers.com/crossover#mac