Different Keyboards produce different results

So this is a weird one:

I broke a key on my keyboard, a Logitech MX Keys for Mac which is connected via the Logitech Unifying receiver USB-A dongle. It's fixable but I didn't want to fix it right away. No big deal, I have at least 5 other perfectly good keyboards. So I pulled out a standard Apple USB extended keyboard (no Bluetooth) and everything seemed to work. Except one thing:

With BetterTouchTool I have one of my mouse's thumb buttons set to behave as the Command key in the "For All Apps" group by using a pair of CMD Key Up/CMD Key Down actions for Button 3, the mouse's thumb button. This works perfectly with both keyboards.

When using a Windows application with Crossover or other varieties of WINE, I use an app-specific group which, when wine-preloader or a variety of other applications are in the foreground, causes Button 3 to behave as the Shift key instead of the All App group's setting for the Command key. This works perfectly with my Logitech keyboard.

But with the Apple USB keyboard, Button 3 is doing nothing. All the other things I have programmed for the WINE group work. For example, I have Button 8 and Button 9, my mouse's scroll wheel rock-left and scroll wheel rock-right, set for left-arrow and right-arrow in the WINE group whereas for my All Apps group those are set to just be a normal middle click. It's only the pair of actions intended to cause Button 3 to act as the Shift key which don't work.

This is really odd because I can swap these keyboards in and out and the Logitech keyboard works perfectly with my WINE group's setup of the mouse's Button 3 as the Shift key. But with the Apple USB keyboard this simply doesn't work: All the other app-specific settings in the WINE group work, but when using the Apple keyboard I can't use Shift plus some keypress on the Apple keyboard to do anything, it only registers the keypress on the keyboard and not the button-down Shift modifier key from the mouse's Button 3.

And the Apple keyboard does register the Command key when any non-WINE app is in the foreground, allowing me to use the mouse's Button 3 as the Command key in combination with keyboard keys to, for example, do copy and paste operations without having to use two fingers of one hand on the keyboard or move my hand off the mouse.

It's not just the presence of the Apple keyboard connected to the system: I can leave the Apple keyboard connected and also connect the Logitech keyboard and the behavior is the same: If I hold down Button 3 on my mouse and tap a keyboard key on my Logitech keyboard while a WINE app is in the foreground, it works as expected giving me the Shift+key combo. But if I hold down Button 3 on my mouse and tap a keyboard key on my Apple keyboard while a WINE app is in the foreground, it only registers the keyboard key – not the Shift+key combination.

Not a big deal, I already have the Logitech's key repaired. But this is very odd and I'd love to know if there is a workaround for this issue with Apple keyboards or if it's some known issue that cannot be worked around.

Thanks for reading! Hope the above was understandable.

I also tried this with an Apple mini Bluetooth keyboard (circa 2013, the kind that takes 2xAA batteries) and had the same results.

That is really weird, if I understand the setup correctly the connected keyboard should not matter at all.

Which version of BTT are you on? There have been some fixes for modifier key behavior in the recent alpha versions

I just updated so as of right now, I am on 4.993 (2024121805) and the behavior is the same. I both downloaded a version of some days earlier as well as the latest version as of yesterday US evening time when I first noticed this and there was no difference in behavior.

Since my first post I checked all the settings for my Logitech keyboard and other than having the function keys locked (i.e. they work as F1, F2, etc. rather than the various UI functions normally assigned by MacOS) I do not have any keys programmed or anything other than defaults set for the keyboard. In function from my perspective – but perhaps not from the system's perspective – it's just like an older Apple extended keyboard except it has a backlight and can connect via that dongle in addition to Bluetooth.

I only tested with one Windows application through WINE yesterday because that is the one I was using at the time my keyboard key broke. Today I have tested with several other WINE applications and using mouse Button 3 as the Shift modifier key in combination with a keyboard key on an Apple keyboard is working correctly with those other applications. So far, it is only the combination of an Apple keyboard plus that one specific Windows application, Lord of the Rings Online for whatever that might be worth, which causes the application of the Shift modifier from the mouse's Button 3 to be ignored. Yet the Shift as modifier plus a keyboard key combination works correctly with the Logitech keyboard in that one application.

I don't expect you to invest the time to figure out what is going on when the problem is isolated to a single application, that application is a Windows application running via WINE, and it's just a game on top of it! I'm sure you have more important issues to track down for BetterTouchTool. It is very odd, though, and if something occurs to you I'd love to know what is causing the problem even if it is something that can't be "fixed" through BetterTouchTool.

Thanks again for this great utility!

Further testing has proven to me that this issue only occurs with Apple keyboards and only with that one application, Lord of the Rings Online which is a Windows application which I run on my Mac with WINE. The problem does not occur with other applications, even other Windows applications running with WINE. And it doesn't occur at all with a non-Apple keyboard, my Logitech keyboard for example works correctly.

So I don't think this is a BetterTouchTool issue at all. Thanks again for your time. If I come up with either a reason for this behavior or a solution, I'll post it here just in case someone else runs into the same problem. No need for you to consider it an issue for BetterTouchTool, though; sorry for the trouble.

So I ordered two new keyboards from two different manufacturers just to test. Can never have enough keyboards anyway, right?

All of them – Logitech, Satechi, Macally – work as expected in all cases including the Windows game played through WINE called Lord of the Rings Online. It's only the special combination of an Apple keyboard (and Apple keyboard, apparently – I tried 5 different models) and that specific game and only that game's keybinds for in-game combat actions that don't work with the mouse button set up as a modifier key.

I don't know why this is the case but that's the way it is! Just thought I'd report that here. It is an oddness and I would LOVE to know why this is the case. But it does not seem to be a BetterTouchTool issue in any way.

As always, thanks for BTT!