Hi Myles,
You need to perform the full check against the URI as string tolower doesn't accept multiple strings.
if { ([string tolower [HTTP::uri]] contains "font") && ([string tolower [HTTP::uri]] ends_with ".eot" || ".ttf") } {
->
if { ([string tolower [HTTP::uri]] contains "font") && ([string tolower [HTTP::uri]] ends_with ".eot" || [string tolower [HTTP::uri]] ends_with ".ttf") } {
If you're doing this many checks on the URI, you should save the lowercase value in a variable:
set uri [string tolower [HTTP::uri]]
if { ( $uri contains "font") && ($uri ends_with ".eot" || $uri ends_with ".ttf") } {
Aaron