First off, let me say how delighted I am to have finally gotten WInbox (64-bit) and Dude (32-bit) running under a common installation of Wine. I can finally stop paying forever for Parallels. (I don't think I did anything different, I think they improved Wine to make this work.)

But on this newer version of Wine, Winbox seems to have picked up an odd and consistent behavior. The chooser window comes up, you click on the desired router, the chooser window blinks, but nothing happens. About 35 seconds later, you get the "blank chooser window" you see when you lose connection with a router, and the message, "Router xxx has been disconnected. Will retry in 5 seconds." It counts down, and then the router window appears perfectly. This happens every time.

It's as if Winbox does immediately connect to the router, but the router window gets displayed in a black hole and you never see it. Then the router disconnects for some reason (consistently in 35 seconds) and when Winbox retries the connection, it's perfect. Earlier versions of Wine did not exhibit this behavior. I'm seeing the new behavior on multiple different Macs.

Has anyone else seen this behavior? Does anyone know how to correct it?

I have exactly the same behavior with WinBox on macOS/Wine (both version 8/9) when "Open in New Window" is checked. I started debugging Wine in a development environment but never managed to identify the root-couse.

The problem closely resembles old MS Windows issues that occurred when a program was started and one of the printers wasn't available. My guess is that there is a similar timeout on some Windows resource.

Same here, "Open in New Window" never worked in wine on Mac as expected and I'm not using it, if I want multiple WinBox instances I just run again winbox64 or "New WinBox" if already connected.

Thanks, you are all 100% right that turning off "Open in New Window" cures this behavior. And since the router window now contains a "New Winbox" menu (I don't think that was always there, or maybe I've just overlooked it since 2006), that's now an easy feature to abandon.

just went to post about this exact issue after switching back to mac from windows after 6 years

using the 'Open in new window' seems to do nothing, then 30 seconds later, displays the 'couldnt connect, reconnecting', then suddently it just appears!

but if you untick the 'open in new window' box it shows straight away,

using old version of winbox makes no difference, same with old wine versions too, so i think its a macos issue maybe?

EDIT: im using intel mac and not arm mac - Sonoma 14.4

I wrote about this years ago, sent tcpdumps, even got reply from Mikrotik's oskarsk: viewtopic.php?p=1041484#p1041484 that they are also affected by this.
I agree that problem is probably in Wine, because it appeared with Wine update from 6 to 7, as per https://bugs.winehq.org/show_bug.cgi?id=52451 but it seems that MT is not being too active in solving this...