The following code will cause the second %ob construct to be made 'oddly'.
The root cause is the %ff%nl that immediately precedes 'Second boxed line of text'. Remove this, and it looks exactly as one would expect.
use mswin
integer i
i = winio@('Text Line 1%nl&')
i = winio@('%1.1ob[named_l][This is a text box]&')
i = winio@('This is a boxed loiine of text%nl&')
i = winio@('%cb&')
i = winio@('%ff%nlIntermediate Text%ff%nl&')
i = winio@('%1.1ob&')
i = winio@('%ff%nl&')
i = winio@('Second boxed line of text%nl&')
i = winio@('%cb&')
i = winio@(' ')
end