I frequently doubt whether I have performed istibra after urinating. Rationally, I think that I usually (perhaps even almost always) perform it as a matter of habit/routine, but after leaving the restroom I often doubt whether or not it was performed. Sayyid Sistani’s ruling is that if an unknown fluid leaves the urethra, it should be treated as impure if one doubts whether or not he performed istibra. Does this pertain to a “frequent doubter” on this matter who genuinely intends to almost always perform istibra anyway? What if such occurences are very common, lead to frustration, and can almost certainly be classified as waswasa?

If it is converted to what is called (waswasat shaitan), then do not bother about it.