Also I noticed in Device Manager it tries to connect to the host activationBBR.mycompany.com:4101. I always thought BB device communicates to BES only via RIM servers. Do I miss anything?
Activations over WLAN bypass the RIM infrastructure and communicate directly with your Blackberry Router on port 4101. Your BB router then sends the activation message to a mail server you define.
I guess that's what the simulater is trying to do.