If there's a specific assert that fits you should always use it instead of assert true, as well as saving typing and typos, one of the key benefits is better error messages e.g assertContains()
Failed asserting that 'foobar' contains "baz".
If that string "foobar" was generated by your programming then seeing it in that message might be all you need to diagnose the problem, maybe it was just a typo, maybe there's several words missing, whatever tyhe problem is this gives you vital context
If it just said "assertion failed" or "true != false" or even a witty message written by hand with no actual knowledge of what has gone wrong in this particulainstance you'd have to spend time establishing that the string got as far as the test and what it contained.
Rather than typing out a message each time you can even write your own assertions that do it for you based on the values you pass in.
You also get a chance to document it with the function and class name, which again can be automatically shown, e.g WhateverTest::