Debian doesn't seem to handle the association between wpa_supplicant.conf records, and /etc/network/interfaces. This is in wpa_supplicant.conf:
This is the interfaces config it should associate with:
# id_str "my_static_lan"
iface my_static_lan inet static
What's happening is there are two gray circles as the wifi attempts to connect. The first one turns green, but it never completes the next step. The syslog shows that it's waiting for the (nonexistent) DHCP server to respond. If I turn on DHCP, the connection completes, but the routing is messed up (because at that point it actually tries to use the static IP from /etc/network/interfaces).
So it seems to associate eventually, but it's way too late. I need it to associate soon enough to know not to attempt DHCPDISCOVER.