Hello Rabbi, I didn’t want to add another question so as not to burden the question database, and therefore, with your permission, I’ll ask here:
My question concerns doubt and double doubt. The simple intuition says that when I am unsure whether the command of the Holy One, blessed be He, applied to a certain situation, I should be stringent and not lenient. That is how we conduct ourselves throughout life in any situation of uncertainty that is fairly balanced, where the other side involves danger, prohibition, and the like.
Now, with regard to double doubt, the Sages say that it has the power to unravel the prohibition that seemingly exists—and this is by force of two doubts (that is, a doubt within a doubt) that exist in that same case. And apparently the heart finds this hard to accept—how can it be that because of two doubts we are not concerned to be stringent regarding a prohibition? If there were five, six, or maybe seven doubts here (one could debate where the line is), I could understand not having to be concerned about a Torah prohibition, but two doubts sounds really far-fetched.
Even according to Rashba’s explanation, there is no logic to it—Rashba holds that this is a majority of possibilities and not a majority of probabilities, so it is even less reasonable to accept this permission of double doubt.
I would be glad to hear the Rabbi’s thoughts.

First of all, who says that in a case of double doubt there is a prohibition? Maybe it is like nullification, where in a double doubt there is no prohibition at all, and then of course there is no need to be concerned. Admittedly, it is true that the law of double doubt is based on reasoning and has no explicit source (unless you say it is a law given to Moses at Sinai), and therefore it is less intuitive.
But note that the question is not where it is proper to be stringent, but where one is obligated to be stringent. It is proper to be stringent even in cases of double doubt (and maybe even in a fivefold doubt). But there is no obligation to be stringent when most of the probabilities/possibilities are on the lenient side.
Something similar can also be seen in nullification by majority. Strictly speaking, it applies even when there is only a slim majority of 51%. Now, one could say that in nullification there is no prohibition at all, but the law of “an item that will later become permitted” shows that this is not so. For if it will later become permitted, then we say not to eat it, because it is better that he eat it permissibly and not through prohibition. This proves that there is still a prohibition/problem even in nullification by majority, except that one is allowed to override it (there is no halakhic obligation to avoid it, though perhaps it is still proper to do so).
And as a side note, it is worth remembering that according to Maimonides, even in a single doubt there is no Torah-level obligation to be stringent.

Have a good week, Rabbi, and thank you very much for the answer.
I would like to make a few comments:
A. You wrote that regarding double doubt, the question is where one is obligated to be stringent and not where it is proper. To that I want to comment that this is exactly my question: why is there no obligation to be stringent in such a case, where there is a double doubt? In other words: if there were some instruction from some authority to perform action X, and whoever failed to do so would lose out or be punished, and now I am uncertain whether a certain action is action X and as a result I refrain from doing it—surely that authority would punish me or make me lose out, on the claim that I ought to have performed that action despite the doubt. Therefore I argue that the simple intuition says there is an obligation to be stringent in such a case, and not merely that it would be proper to be stringent, and so it is unclear why there is an exemption in a case of double doubt.
B. As for the comparison to the law of nullification by majority, first of all I liked the proof that the prohibition still exists—more power to you. But that still doesn’t solve the problem; at most, this is just an English-English dictionary. So now we have another case, similarly strange to the present one, and that too should really be explained. What is certain is that the simple intuition does not say this, and so the question remains: why does double doubt (which, as agreed, is based on reasoning) help undo a Torah prohibition?
C. As for Maimonides, I did in fact want to mention his words, but refrained so as not to go on too long. In my opinion Maimonides’ view is not intuitive—why should the instruction to be stringent in a doubtful prohibition be only rabbinic and not from the Torah? The simple intuition (and perhaps therefore reasoning itself is Torah-level) says that one should be stringent. After all, with any command or instruction where we are uncertain whether it must be fulfilled or not, we understand that one should be stringent and fulfill it rather than refrain. So in my view Maimonides’ position itself requires analysis, and therefore it does not seem to me that my question can be answered through his view.
Thank you, and have a successful and excellent week!

P.S.
I forgot to mention in my previous remarks: more power to you for the wonderful books and enlightening articles.

A. Why should there be an obligation? Not everything that is proper is also obligatory. Otherwise you would leave no room for going beyond the letter of the law. You yourself wrote that with five doubts you would understand why one could be lenient, so where exactly, in your opinion, is the line crossed? This is precisely what the medieval authorities dispute: whether it is after one doubt (Maimonides) or two (Rashba). I do not see a question or a problem here.
B. You can call something an English-English dictionary when I use one thing to explain the other. That is not what I did here. I brought another example of the same phenomenon. That’s all. The first case is not strange, and neither is this one. All in all, I showed you that in Jewish law there are cases where it is proper to be stringent even though one is not obligated, and I argued on that basis that this is also the case in double doubt. You refuse to distinguish between what is proper and what is obligatory, and I do not understand why.
C. See my answers in the previous sections.

Gladly.

In a single doubt, you fulfill the command.

In a doubt about a doubt, you fulfill the doubt, regarding which the Torah gave no command.