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Question: I am careful to finish Mincha by shki’ah (sunset), but one day I remembered a few minutes after it, that I had not davened. I decided to daven then with the following condition – if it was still time for Mincha, it should count, and if it was too late, it should be a tefillat nedava (voluntary prayer). Was that correct? Also, what was I supposed to do when I went to daven Ma’ariv, considering that I am unsure if I fulfilled Mincha?

Answer: Indeed, one should daven Mincha by shki’ah. Although the Rama (Orach Chayim 233:1) says that those who daven Mincha after plag hamincha (now widely practiced) have until [close to?] tzeit hakochavim, the Mishna Berura (233:14) argues that one must daven by shki’ah. However, at least for several minutes after sunset, it is possible that b’di’eved one may still daven Mincha (ibid.).
You seem aware of the above and do not want to rely on the opinions (many do for at least several minutes) that when one must daven Mincha after shki’ah, he may assume it works. Your idea of dealing with the doubt contains positive points. Let us analyze it and determine how you should have proceeded.
Classical sources discuss tefillat nedava in two cases – #1. One who is unsure if he already davened may do Shemoneh Esrei (=SE) as a nedava; #2. One who wants to daven a second time and adds new elements to SE (Shulchan Aruch, OC 107:1, based on Berachot 21a). Your idea relates to #1, with the doubt being not whether the tefilla is necessary but whether it works as desired (for Mincha). There is no clear precedent for a tefillat nedava at a time that is not viable for tefilla, but your assumption (the Be’ur Halacha to 233:1 concurs), is that if it is too late for Mincha, it must be possible to daven Ma’ariv. Your nedava faces another challenge. If your tefilla did not work for Mincha, it is nedava of Ma’ariv … before you do the obligated Ma’ariv. This might be possible (see Ohalei Shimon, Tefilla 20), but it is difficult to determine if all agree with this possibility.
We now follow your system to Ma’ariv. If your tefilla did not count for Mincha, you needed SE at Ma’ariv twice, the second as tashlumin (makeup) of Mincha (Shulchan Aruch, OC 108:2), for a total of three SEs that evening. On the other hand, you could not be sure the third one is necessary, because if the first counted for Mincha, no tashlumin was necessary. Therefore, the third tefilla would also need to be to be done as a tefillat nedava (a variation of scenario #1 above).

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However, poskim (see Ishei Yisrael 27:6) do not embrace your system of dealing with the safek, but that of the Be’ur Halacha (ibid.). He says that post-ski’ah SE should be on condition that if it does not work for obligatory Mincha, it should be for obligatory Ma’ariv. If the first was for Ma’ariv, then you missed Mincha and the later SE (which will be preceded by Kri’at Shema and its berachot) will be tashlumin of Mincha.
The Be’ur Halacha’s system has weak points if your first tefilla did not fulfill Mincha. SE of tashlumin should be directly after the SE of the present tefilla (Mishna Berura 108:15). In this case, if the SE after shki’ah ended up being for Ma’ariv, then the tashlumin, done with the Ma’ariv of everyone else, is likely to be several minutes and perhaps much more after the first SE. However, when need be, there can be a break, as long as it is within the timeframe of Ma’ariv (ibid.). Also, Kri’at Shema and its berachot will turn out to be (perhaps, significantly) after the main SE of Ma’ariv (the first tefilla). Once again, while not ideal (Shulchan Aruch, OC 236:2), it is permitted when there is need (ibid. 3).
The Be’ur Halacha avoids two weaknesses in your system that exist even if, as is likely, your first tefilla worked for Mincha. 1) You need three SEs instead of two; 2) We try to avoid tefillat nedava, which should ideally be done only if one concentrates throughout SE (Shulchan Aruch, OC 107:4).
While we can further debate the merits of each system, we expect that next time you will follow the Be’ur Halacha.

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