Everyone hears that a rabbi "has" to discourage a conversion candidate 3 times. Some rabbis don't hold by that at all. Some do exactly three and then will begin a congenial conversion learning process. Some may or may not obviously discourage before working with you, but will continue to discourage you regularly and to varying degrees of questionable ethics. I don't think I'll ever forget the rabbi who would schedule appointments with me and then just not show up. He "forgot." At the time, I just thought he was disorganized and possibly rude, but with the benefit of hindsight, I believe it was on purpose. And to this day, I personally think that's going "beyond the call of duty," so to speak. Notably, this was not an orthodox rabbi. This is not solely an orthodox problem, though I suspect it is more widespread and generally more severe in orthodox conversions. Discouragement is one thing. Rudeness, poor manners, and cruelty are another. As if the Holocaust, anti-semitism, and kashrut aren't enough to discourage the average person from converting to Judaism!
Rabbis are one thing.
All the other Jews is another.
Every time someone has quoted that discouragement idea to me, they talk about rabbis. So then why do non-rabbi Jews like to get on the discouragement bandwagon? I personally haven't had much of a problem with this, but it's one of the most common "bad experiences" I hear from other converts. Other Jews seem to feel perfectly comfortable telling conversion candidates that Jews will make them miserable, no one will ever want to marry them, and no one will accept them or their children as Jews. Or any other thing they can think of to "fulfill the mitzvah of discouraging the potential convert." I'm sorry, but I don't believe that's your mitzvah to fulfill. Just like it's not mine to slaughter sacrifices in the place of a kohen.
Dear Jewish public:
It is up to the rabbi to decide when and if a conversion candidate should be discouraged. In fact, you probably don't know enough about the conversion candidate to make a halachic ruling whether discouragement would be a) appropriate and b) necessary. This is not your responsibility, nor your place. Cease and desist. Once it crosses a certain point, I'm physically incapable of fulfilling the mitvah of judging favorably because your behavior is so irrational, cruel, and misguided.
Of course, there is the idea of the mitzvah not reminding a convert of his past and all the interpretations of that mitvah, but that only applies after the conversion is complete. And that is a totally different post that will come soon enough.
Let's look at a more foundational problem here, both with rabbis and laypeople: The ends do NOT justify the means. Nine times out of ten, rabbis are (really) genuinely nice people, but they can get caught up in this discouragement cycle, especially as the orthodox conversion procedures spiral out of control in a quest to become "unquestionable." These people don't realize the harm they're doing to conversion candidates and that the convert will remember every single cruel word, rude act, and other poor behavior. Eventually converting them is a wonderful end for the convert, but the average convert is not suddenly going to understand the pain you caused him/her, forgive you, and feel buddy-buddy with you. They will remember the means you used, and it can have long-lasting emotional and psychological effects. Most notably, it can create a deep-seated distrust of the clergy and anyone else in power in the Jewish world.
I think it's most telling that when I think about these stories, I think of an abused dog who forever jumps at loud noises and always wonders if his owner is going to pet him or hit him.