CDK tooling cannot get into Started state even though cdk is actually started on windows 10

1. Prepare CDK server adapter and have CDK 3.16.0 set (setup-cdk called)
2. Start server adapter
3. ASSERT: adapter is in starting state and Job 'Starting Container Development Env.' is running - PASS
4. ASSERT: Progress from cdk in Console log suggests that cdk is successfully approaching spinning up all tasks - PASS
5. ASSERT: Inspecting CDK environment job is being executed and Openshift connection is created, user is asked to accept SSL Self Signed Certificate - FAIL
Actual result: Error saying that CDK failed to start appears (or similarly just with timeout), though, console log shows that CDK is started.

I am suspecting latest windows 10 update (now running build 18363 - version 1909)

See attached pic: