Azure AD access token lifetimes are around 60 minutes by default. You may be 
able to change this according to 
https://learn.microsoft.com/en-us/azure/active-directory/develop/configurable-token-lifetimes.
 I believe until access token is refreshed, WAP will not pass traffic since the 
access token is no longer valid.

Application proxy currently does not have support for WebSocket according to 
https://feedback.azure.com/d365community/idea/8fc692de-bb25-ec11-b6e6-000d3a4f0789.
 In the event Guacamole cannot use WebSocket, it will fall back to HTTP and you 
will see the message below.

We have a similar setup using Cloudflare Access/Tunnel and it has worked very 
well for us.

Best regards,

Stephen Cluff, Solution Architect
ecomm911.ca<https://www.ecomm911.ca/> 
@EComm911_info<https://twitter.com/ecomm911_info>
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From: Dose, Volker <[email protected]>
Sent: Thursday, July 20, 2023 1:50 AM
To: [email protected]
Subject: Guacamole and Microsoft Web Application Proxy


* This is an external E-Mail, please take caution when clicking on links or 
opening attachments unless you recognize the sender *
Dear all,

we are using Guacamole 1.4.0 in combination with a MS WAP. This WAP server 
forces the user to authenticate against AD FS and only after a successful 
authentication the user gets to Guacamole to work with.

Generally speaking this setup works, bur we are facing some issues with it:


  1.  Every 60 minutes the session is disconnected - after pressing F5 the user 
is able to work, but this is a bit annoying


Catalina.out shows a line like this:

17:08:13.871 [main] INFO  o.a.g.rest.auth.HashTokenSessionMap - Sessions will 
expire after 60 minutes of inactivity.

But the session breaks even if the user in active all the time




  1.  We can upload files to the TRANSFER drive, but download does not work - 
only for files with 0 bytes



  1.  Websocket does not work at all, Catalina.out shows this


16:59:40.785 [http-nio-8080-exec-15] INFO  
o.a.g.t.h.RestrictedGuacamoleHTTPTunnelServlet - Using HTTP tunnel (not 
WebSocket). Performance may be sub-optimal.


Does anybody have a similar setup? Can someone guide me to the right direction? 
I'm a bit out of ideas right now..


Best regards

Volker Dose
IT-Infrastruktur

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