The parashah begins with the words (21:10) אויביך על למלמחה תצא כי, "When you go out to war against your enemies." The Imrei Elimelech of Gradzisk zt'l says this refers to the war we wage on Rosh Hashanah against the Satan. The Satan prosecutes against us, and we battle with him and seek to attain Hashem's compassion.
The question is, why does it say תצא כי למלחמה, "When you go out to war," if on Rosh Hashanah, we are already on the battlefield? The Imrei Elimelech explains that we begin the war in Elul, and the pasuk refers to the war we wage already then.
He writes, "This pasuk refers to Rosh Hashanah, the day of judgment when mankind stands before Hashem in judgment. But, on Rosh Hashanah, the day of the war, one can't say תצא כי, that he goes out to the war because he is already in the midst of the battle. Rather, the pasuk alludes to going out to the war before the day of judgment arrives. It refers to when we prepare for the war with teshuvah, tefillah, and tzedakah. If we prepare, we will win and be found worthy in the judgment. The Torah promises us בידך אלקיך 'ה ונתנו, Hashem will give us success [and we will be acquitted] on the day of judgment."
The Torah also hints at Elul in this week's parashah with the words (21:13) אביה את ובכתה ימים ירח אמה ואת, "She shall weep for her father and her mother for a full month." The Zohar (Zohar Chadash 72.) states, "This pasuk refers to the month of Elul," the month we do teshuvah with tears.
Reb Chaim Vital (Eitz HaDaas, ירמוז או) writes, "The primary time for teshuvah is in Elul, called ימים ירח, because that is when your tefillos are answered."
Chasam Sofer (Sefer Zikaron, Drashos Chasam Sofer Erev Yom Kippur) writes, "Elul is called ירח ימים, which is the same gematriya as ח"שי, which means prayer. This implies that during this month, one should pour his heart out in prayers before Hashem, and Hashem will accept his tefillos. There are forty days from rosh chodesh Elul to Yom Kippur. If you add the 'מ (gematria forty) to ח"שי, it becomes ח"משי, because this brings the redemption near." We understand from this that we should daven for Moshiach in Elul.
It states (Shemos 21:13) לך ושמתי לידו אנה והאלקים שמה ינוס אשר מקום, "...I will make a place for you to which he shall flee." The holy sefarim write that the roshei teivos of לך ושמתי לידו אנה spell out the word אלול. These are the days we can flee and escape from the yetzer hara and begin on a new path.
In Shu't Divrei Chaim (Yorah Deiah vol.1 33), Reb Chaim of Sanz responds at length to someone's halachic shaila. The person who sent him the question also wrote to him a pilpul, not related to halachah. The Divrei Chaim didn't comment on that part of the letter. Instead, he wrote, הזמן אין בעלמא ולפלפולא הללו נוראים בימים לבב משכיות חדרי לבדוק צריך כי גורם ז"תרי אלול, "Just to discuss pilpul, this isn’t the best time, because we have to check the corners of our hearts in these awesome days of Elul, 5617."
What could be better than discussing divrei Torah? The Divrei Chaim certainly did discuss divrei Torah all day long, also in Elul. Nevertheless, he didn't have time for pilpul because he needed time for self-reflection, to think about his deeds, and to seek how to improve.
Tehillim and the Power of Prayer in Elul
The Shaar HaMelech concludes: "So, recite Tehillim with kavanah and tears, and say the tefillah after each sefer of Tehillim. There should be ten people saying Tehillim, and they should also say the thirteen attributes of mercy until the end of the prayer. If you know of a place or city that doesn't know of this good custom, you should inform them of it so that every day of Elul we will be with the Tehillim. Our Tehillim will be precious to Hashem as though we had studied the laws of negaim and ohalos, and the merit of Dovid HaMelech a'h will protect us, to receive a good judgment, for life and peace."
The Nesivos Shalom zt'l (Slonim) was very ill at the end of Av, and the doctors recommended emergency surgery. The Nesivos Shalom wanted to postpone the operation until after the yomim noraim. He explained that we believe that Rosh Hashanah is when decrees are passed, and we can daven and merit a good year. The family realized that the Nesivos Shalom was firm with his resolve and asked the doctor to come to him. The doctor told him how to take care of himself throughout this waiting time. He told him what he should eat, how much to sleep, etc. The day after Yom Kippur, he was brought in for surgery. The doctors checked him and saw that he no longer needed the surgery. One doctor commented, "Time was good for you." The Nesivos Shalom replied that it was indeed the "Time" that helped him. The days of Elul and the yomim noraim were good for him because he changed his destiny with his tefillos during this time.
The Rebbe Rashab of Lubavitz zt'l said, "Elul is the season for saying Tehillim." (He said this when he sent his gabbai to buy him a Tehillim in Elul.) Shaar HaMelech (1:2) writes, "I saw a good custom in many communities, and my parents also told me about this good custom. From rosh chodesh Elul until Yom Kippur, immediately after Shacharis, they say Tehillim with tears and sweet voices. I decided to bring this good custom to our city. Tehillim is needed because our primary goal this month is to remove the mastinim (mekatrigim who speak against us)... and nothing stops them as well as when we say Tehillim. Tehillim is called mizmorim, which also means to shear, because the Tehillim shears away all thorns [of the mekatrigim]."