I've been getting this problem for some time now, about 1 in 3 (my estimate) boot attempts with my desktop the wireless link to my AP fails to be established.
The symptoms are that dhcp can't be established and the only way out of it is to either re-boot or to restart the networking service. I've ignored the problem for ages but have finally decided to look into it and every time it happens the message in the logs is that it is deauthenticating because of "reason 6". I've looked up what "reason 6" means and it appears that the AP has instructed the client to deauthenticate because there has been an attempt to send data before the client was authenticated.
I'm using Debian Testing.
This problem has been with for at least the last three kernel versions; I'm currently on 3.0.0-1-amd64.
The module in use is rt61pci.
I'm using the plain kernel package from the Debian repositories.
I use wpa_supplicant.
Once wireless is up and running it's up good and proper, this problem strikes only at boot time.
I've already tried switching off power management and hardware encryption, neither have cured the problem.
I did consider raising a Debian bug but thought it would only get passed upstream anyway.
I've searched on-line for someone else with the same problem and can't find anything the same (some similar problems though) so it might be a strange edge case with my combination of wireless card and motherboard.
Any help at debugging the problem would be appreciated.
* Update 30 Nov 2011*
Still get the problem with kernel 3.1.0-1-amd64