ok. Running guacd under daemon was the problem, it has to run under guacd user. 
A good summary and quick instructions was here

https://kifarunix.com/install-guacamole-on-debian-11/#fix-rdp-security-negotiation-failed
 
<https://kifarunix.com/install-guacamole-on-debian-11/#fix-rdp-security-negotiation-failed>

Can anybody explain what is specific about connecting to Windows 10 pro that it 
requires guacd to run under the guacd user with a writable directory?

thanks!

> On Aug 20, 2022, at 8:23 AM, Doug Baggett <[email protected]> wrote:
> 
> On the guacd user account thing again….so I shouldn’t be running under the 
> daemon user? 
> 
>> On Aug 20, 2022, at 8:01 AM, Doug Baggett <[email protected]> wrote:
>> 
>> Thanks for the tips. Here are some details
>> 
>> - It’s a pretty bog standard guacamole installation. Not in docker container 
>> or anything like that.
>> - Ignore server certificate has been checked. 
>> - Set it to NLA (or any setting)
>> 
>> On the tip on the guacd user account. I’m not having problems with any other 
>> RDP connection. It’s JUST to the Windows 10 system I’m connecting to. Using 
>> RDP to a Linux system with xrdp works fine, so it would seem that a 
>> permissions problem with guacd would affect all RDP connections and not just 
>> one to a vanilla Windows 10 pro system.
>> 
>> Guacd keeps complaining that security negotiation failed - wrong security 
>> type? But I’ve tried every option and they all fail.
>> 
>>> On Aug 20, 2022, at 7:46 AM, Nick Couchman <[email protected]> wrote:
>>> 
>>> On Sat, Aug 20, 2022 at 7:40 AM Doug Baggett <[email protected]> wrote:
>>>> 
>>>> Hello and thank you!
>>>> 
>>>> So I’m pretty frustrated. I can connect using RDP to an xrdp enabled linux 
>>>> system, but no matter what I try I can’t authenticate or connect to my 
>>>> windows pro 10 system. I know the windows firewall is set up correctly 
>>>> because I can connect using a native RDP client on my Mac to the Windows 
>>>> system using the email associated with my Microsoft account and password. 
>>>> I’ve tried every combination of settings I can think of and I keep getting 
>>>> login failed.
>>>> 
>>>> Can somebody reply with the **EXACT** settings they are using with an RDP 
>>>> connection to windows 10 in Guacamole to log into a Windows 10 system?
>>>> 
>>> 
>>> Well, no, we cannot tell you all of the exact settings to use to do
>>> this, because some of them will be very specific to your environment,
>>> and I don't know what that looks like. However, I can tell you the
>>> following things to look at:
>>> * Try specifically setting the security mode to NLA, as every version
>>> of Windows since 7/2008 required this by default.
>>> * Try checking the box to disabled certificate checking to see if that
>>> helps. Ultimately you'll not want to keep this checked and you'll want
>>> to make sure that you have certificates set up correctly, but it's
>>> helpful for debugging.
>>> * Make sure that the user account under which guacd is running has a
>>> valid home directory and can write to that directory.
>>> * Look at guacd logs and see what it's telling you. If necessary,
>>> change logging for guacd to debug.
>>> 
>>> -Nick
>>> 
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>> 
> 

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