iwevent will list hardware sputterings and some network changes. wpa_supplicant has a debug mode that will show connection failures (assuming WPA is in user)
Depending on how old that model is, it is possible the WiFi chipset is not properly supported by the Linux drivers in that Ubuntu release. There are three chips listed for the T41: Intel, Atheros and Cisco. The Intel drivers have been reliable for a long time, the Atheros drivers had some issues until ~2010. I've never dealt with the Cisco Aironet chipset.
The drivers, open source or otherwise, need binary firmware blobs. Getting the right/latest version of those was tricky as well as sometimes you had to hack it out of the Windows drivers. There are some tools for that in the repositories, but more recent Debian distros now have the firmware in non-free and at least this problem has gone away.
(The binary only firmware is a consequence of the FCC regs to avoid interference.)