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https://issues.apache.org/jira/browse/GUACAMOLE-657?page=com.atlassian.jira.plugin.system.issuetabpanels:comment-tabpanel&focusedCommentId=16682188#comment-16682188
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Michael Jumper commented on GUACAMOLE-657:
------------------------------------------

{quote}
Mapping the Windows key to Meta would solve this issue? Or is this a deliberate 
design choice?
{quote}

It would result in a corresponding key event being received within the remote 
desktop for the Command key. That said, I'm concerned that "fixing" the mapping 
will result in real strange behavior for Mac users accessing Windows machines 
when they reflexively type Command+Anything and end up opening the start menu. 
Testing will need to be done before that deceptively minor change can be made 
to the keymap.

{quote}
The "Ctrl" key release is not send from the browser to Guacamole as a WebSocket 
frame (from what I can observe from the Chrome developer) and therefore will 
never reach the VM in the first place. I would assume this is a legitimate bug.
{quote}

If this is true, then yes, but so far I am unable to reproduce what you 
describe. Testing with a Mac, I see both a Ctrl press and release. I also don't 
see how such a bug could exist given the way the Guacamole menu works - the 
code that opens the menu also invokes {{reset()}} on the 
{{Guacamole.Keyboard}}, sending release events for absolutely all pressed keys:

https://github.com/apache/guacamole-client/blob/823bbeace11063b249e3f05c2a1e5c5027107b96/guacamole/src/main/webapp/app/client/controllers/clientController.js#L540-L547

If a press event for any key was sent to the remote desktop, a corresponding 
release event would then be sent when the menu is opened as a result of that 
invocation of {{reset()}}. I'm thinking there must be some other cause behind 
what you're seeing (an application within the remote desktop not receiving the 
release event for Ctrl) which is not that Guacamole is not sending that event 
(I expect it is).

> Unexpected behaviour of modifier keys when opening Guacamole menu
> -----------------------------------------------------------------
>
>                 Key: GUACAMOLE-657
>                 URL: https://issues.apache.org/jira/browse/GUACAMOLE-657
>             Project: Guacamole
>          Issue Type: Bug
>          Components: RDP
>    Affects Versions: 0.9.14
>         Environment: Host: macOS Mojave
> Browser: Chrome 70
> Guest: Kali Linux (VirtualBox 5.2.18)
>            Reporter: Kaspar Hageman
>            Priority: Minor
>
> When opening the Guacamole menu, during an RDP session with a VM, with the 
> default key combination (Ctrl + Cmd + Shift), the VM does observe key events 
> as expected.
> For instance, when pressing Ctrl + Cmd + Shift (in that order), the following 
> key events can be observed (using Chrome's developer tools):
>  * Ctrl pressed
>  * Cmd pressed
>  * Shift released
>  * Ctrl released
>  * Cmd released
> However, in the VM, the following key events can be observed (using xev):
>  * Ctrl pressed
> Has been tested with both version 0.9.14 and the current master branch 
> (d4f58f2c0d812b05c392e06438e659902e8121f8)



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