The first question that must be asked is when does a person have to say Tefillat HaDerech? Is merely walking next door considered to be a sufficiently long trip to obligate one in this prayer? The answers to this question will stem from how one understands the main point of this prayer - travel was considered to be a dangerous endeavor (more so than it is today), and thus any trip that was deemed to be dangerous required that one recite this prayer. There are two main views with regard to this point. The first is that of the Behag, who states that a journey must be a parsa (3-4 miles) long in order for one to have this obligation. The Ra'ah, on the other hand, says that the journey itself can be of an even shorter length, but if a person leaves his city (meaning leaves the area of settlement) then he is obligated, as he thus enters a dangerous travel situation. According to the Derisha, all roads are the same with regard to Tefillat HaDerech, and the only issue is whether or not one says the blessing at the end.

The bigger question is at what point on the journey one must recite this prayer. The text of the gemara, according to Rashi (and what is printed in our editions) is that one says Tefillat HaDerech from the time that he is "mehalech" - from the time that he walks along the road. However, the text of Rosh and others reads from the time that he is "yochaz" - from the moment that he is considered to be firmly along the road. Is there a practical difference between these two versions?

Let us begin with Rosh. He states that one recites Tefillat HaDerech from the time that he is firmly on his way and can recite it until he has completed the first parsa of his trek. He backs this up by citing a view that claims that the first parsa is considered to be the stretch in which one establishes himself along the road, after which point a person should no longer recite this prayer. Rabbeinu Yonah expands this law some what. He claims that during the first parsa is the optimal time (l'chatchila) for one to recite Tefillat HaDerech, yet he may still do so afterwards so long as he has a significant distance to go. He makes the comparison to tefillin and tzitzit, which require that one make a blessing over them when putting them on, yet one may make the blessing so long as they are still on him and he is still fulfilling the commandment. So too here, so long as one is till on the road and thus in a position where he needs the help of Hashem to protect him, he may say Tefillat HaDerech. Rav Moshe Herschler, in his footnotes on Ritva, explains the root of the argument. He claims that the difference in the texts is very revealing. According to the text of Rashi, the obligating factor is the mere fact of being on the road (mehalech). Thus, Eliyahu said that one should consult their creator when they leave their city - one only says Tefillat HaDerech while they are leaving their city. Once one has traveled a parsa, they are no longer seen as being in the process of leaving, and thus they may no longer say this prayer (at least not optimally). However, according to the second version of the gemara, the obligating factor is the need to pray for one’s safety. Since this applies the entire length of the journey, one may recite Tefillat HaDerech the entire time.

An interesting sidelight to this discussion comes from a law that does not exist. Rambam does not mention at all what we know as Tefillat HaDerech. What he does mention (Hil. Berachot 10:25) is a prayer mentioned in Berachot 60a that one says upon entering and leaving a city. There are two possibilities that can be suggested here. The first is that Rambam considers this to be Tefillat HaDerech, or at least feels that mentioning this law is sufficient to include our Tefillat HaDerech as well. The second possibility is that what Rambam codifies is a completely different prayer (as would be implied by the fact that it is mentioned in a completely different part of the gemara), and that this prayer that he mentions is the one that one makes when leaving a city, this filling the requirement according to Rashi. That said, the requirement according to Rosh and others, of reciting a prayer to ask for protection while traveling, is fulfilled by what we refer to as Tefillat HaDerech. Again, I don't know if either side is more convincing, and the omission by Rambam remains an enigma.

Practically, the Tur adopts the second view. He states that Tefillat HaDerech is said only after one has established himself along his way, and may say it for the entire length of the journey. The one exception is in the final parsa of the trip, when one may still say it, but without the blessing at the end. Since personal danger is the prime factor, and that danger is at a minimum by that part of the journey, we do not want one to say a blessing that is potentially in vain. The Taz mentions a custom not to say Tefillat HaDerech until one has completely left the city from which he is traveling, although he rejects this as being baseless. However, a later opinion, the Be'er Heitev, claims that one should wait until they have left the perimeter of the city (70-2/3 amot beyond the last houses) before reciting it.

The final issue to deal with in this section is how often one has to say Tefillat HaDerech over the course of one trip. The Tur states that if one stopped midday in a city, he does not have to say Tefillat HaDerech again when he continues his journey that same day (such as when embarking on the second leg of an air journey after a stopover). However, the Beit Yoseif notes, in the name of the Kol Bo and the Semak, that if one arrived in a city with the intention of staying there over night, and afterwards decides to continue his journey, he has to say Tefillat HaDerech then, even if he already said it once that day, as his thoughts detached him from his original recitation (hesech ha-da'at). Finally, the Bach points out that Tefillat HaDerech must be recited everyday when one once again sets out to the road, not just on the first day of the trip.

The gemara cites an debate about how Tefillat HaDerech should be said. Rav Chisda claims that it should be said standing, while Rav Sheshet allows for one to recite it while sitting. The conclusion of the gemara seems to indicate that Rav Sheshet concurred that standing was the more preferable way. According to Tosafot, the gemara adopts the view of Rav Sheshet, although both the Tosefta and Rif hold that it should be recited while standing (i.e. one should stop their animal/car if possible in order to say Tefillat HaDerech). Further in the Rishonim, Rosh sides with Rav Chisda while Rabbeinu Yonah stands by the view of Rav Sheshet.

The Tur holds that one must recite Tefillat HaDerech while standing, although the Beit Yoseif elaborates and claims that even Rif only mandates that one stop if it is possible to do so, such as in a situation where those that he is traveling with also stop. However, if it is not possible to stop, then the law of Rav Sheshet is a perfectly valid option. The Shulchan Aruch claims that it is better to recite it standing, but if one is in motion there is no need to stop to recite it.

There are two main textual issues involved in Tefillat HaDerech. The first one stems from the gemara in Pesachim 104b. There it states that all blessings begin and end with a blessing ("baruch ata...") except for those made on the performance of mitzvot, those made on fruits, a blessing that is adjacent to another blessing, and the final blessing of Kriat Shema. What are the reasons for these exceptions? A blessing that is adjacent to another blessing, such as the blessings of the Shemoneh Esrei, while each blessing does not in and of itself begin with a blessing, is immediately preceded by a blessing, and thus the requirement is fulfilled. The final blessing of Kriat Shema is considered to fall under this category. Blessings on commandments and fruits are considered to be too short and to not have enough content to even have a need to fulfill this requirement (see Rashbam ad loc.). Tosafot there ask what about Tefillat HaDerech? The answer given is that it is not a real blessing, but rather a mere supplication for Hashem's mercy. If that is so, then why does Tefillat HaDerech end with a blessing? The answer can be inferred from the continuation of Tosafot (as the Tur does), where they claim that the blessing made after the reading of the Megilla ends with a blessing because it is long and has significant content. Perhaps the same claim can be made for Tefillat HaDerech.

However, all is not so simple for Tefillat HaDerech. Rashba points out that this is one of the blessings that ends with a blessing even though it does not begin with one. While that statement may seem to imply that it is fine the way it is, there are those who are not so sure of that fact. Rabbeinu Yonah feels a need to justify this fact. He claims that since the blessing of Tefillat HaDerech ("Shomei’a Tefilla") is a blessing adjacent to another when recited in its usual context (namely as the final blessing of the middle section of Shemoneh Esrei), it does not need to be made adjacent to another blessing if it is recited out of that context, as it is here. However, both the Tur and the Beit Yoseif refer to the Maharam MiRutenberg who would always make sure to recite one of the morning blessings immediately before Tefillat HaDerech when embarking on a journey in the morning. The Perisha adds in that when traveling during the day, one should precede Tefillat HaDerech with either "asher yatzar" (said after relieving oneself) or the afterblessing said over a piece of fruit (i.e. either Borei Nefashot or Al HaMichya, where the final words of the blessing are the blessing itself).

The second textual issue stems from a debate in the gemara. The original text given is all in singular. Abaye objects and claims that one should recite Tefillat HaDerech in the plural so as to join himself in with a larger congregation. The Tur and Shulchan Aruch both codify the view of Abaye, and the Machatzit HaShekel explains that there are certainly others traveling somewhere in the world at the same time, and thus one joins his prayer to theirs.

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