We have a similar setup where a bastion guac server facilitates RDP logins to a farm of windows instances. In our case both are in AWS so only the guac server is visible to the outside world. I believe I remember having a similar issue. First thing I would check would be to run some sanity tests on the VPC settings between your guac and windows instances.
Daniel McCarty Director of Engineering W. H. Leary Co. P. +1 708.444.4900 E. [email protected] | W. whleary.com<http://www.whleary.com> From: Jim Sullivan <[email protected]> Sent: Wednesday, March 9, 2022 7:59 AM To: [email protected] Subject: Re: [External] Connect to an AWS instance Dan: I am using putty SSH client to reach my Guac server instance and Windows Remote Desktop to connect to the Windows instance. Jim Sullivan 917-837-5210 Sent from my iPhone Please excuse any typos On Mar 9, 2022, at 08:28, Daniel McCarty <[email protected]<mailto:[email protected]>> wrote: Hard to say without knowing more about your AWS setup. Most likely this is your firewall and/or VPC settings within AWS. Can you reach the instance via other means? Public IP, ssh, etc. Daniel McCarty Director of Engineering W. H. Leary Co. P. +1 708.444.4900 E. [email protected]<mailto:[email protected]> | W. whleary.com<http://www.whleary.com> From: [email protected]<mailto:[email protected]> <[email protected]<mailto:[email protected]>> Sent: Tuesday, March 8, 2022 7:22 PM To: [email protected]<mailto:[email protected]> Subject: [External] Connect to an AWS instance I am trying to use Guacamole to connect to an AWS instance using RDP. However, the connection does not happen, and I get the connection is taking too long. I believe I have the configurations correct. Any help would be great. 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