The issue is present in 2.6.1, 2.6.0 still worked. I have a desktop shortcut to open whiskermenu via 'xfce4-popup-whiskermenu'. When opening the menu and then closing it via 'ESC' a subsequent opening does not work but the third opening will work again. When closing the menu via the shortcut (xfce4-popup-whiskermenu) the behaviour is as expected.
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That fixes the issue for me, but I noticed another case when the menu does not open the first time, not only when using ESC but if I open the menu and switch to another window. For example by using a keyboard shortcut to open a terminal, or by pressing alt-tab to switch to another open window.
Whisker Menu now hides on loss of focus (to fix a bunch of bugs that happened from the grab code, and to support on-screen keyboards). Xfce sends a focus out event when you press a key to do a shortcut, so Whisker Menu thinks it should hide. Then Xfce sends the remote event telling Whisker Menu to toggle visibility--since it is hidden, now it is shown. Always.
So I have been trying to find ways to detect when focus is lost because of the remote event versus focus being lost in any other way (clicking on the desktop, alt-tab, etc). There really isn't one, sadly. My first approach was time-based (ick) and it worked for you in 2.6.0, but on slower computers it didn't (see issue #61 (closed)). The only thing I found was a hack to detect when you click on the desktop and are running Xfwm. In all other cases, Whisker Menu can't distinguish between how it lost focus.
Sorry for necrobumping, but this still appears to be an issues in version 2.7.2-1 (Debian 12). So, I' running the openbox window manager inside Xfce4 and indeed, the following happens
open menu with keyboard shortcut
click somewhere else (which results in the menu being closed)
keyboard shortcut must be pressed twice for the menu to open again
Since on clicking somewhere else the menu is closed, I suppose there has to be a way to detect the close-event in order to set the internal menu-state to closed. So, I would kindly like to ask, whether you could take a look at this issue again.
I am using the 2.6.2 and ahh I get it. You have to have Whisker on the panel to trigger it. I thought you can do that even when it is not added to the panel. I wanted to create a custom desktop file with "xfce4-popup-whiskermenu", to then add it to the system. Makes sense. Sorry about the confusion.