The Kitzur Shulchan Aruch, in his introduction to the laws of the month of Elul, after describing the uniqueness of Elul and it’s appropriateness for Teshuva, lists four acronyms relating to Elul. Besides the most well-known – “ani ledodi vedodi li”, there is – “et levavcha v’et levav”, and also “ish le’re’ehu u’matanot la’evyonim”.
The author explains the connection between these as follows:
These acronyms are an allusion to three things: Repentance, Prayer and Charity which must be practiced zealously during this month. “Hashem will circumcise etc.” alludes to repentance, “I am my Beloved’s etc.” alludes to prayer, for prayer is the song of love. “One to another and gifts to the poor,” alludes to charity.
The first acronym however, is possibly less well-known, though the Kitzur Shulchan Aruch quotes it in the name of the Ari Z”l:
The Ari (Rabbi Yitzchak Luria), of blessed memory, wrote, “If he did not lie in ambush but Hashem made it happen, then I will provide …” (Exodus 21:13) the initials of the words [ina le’yado vesamti lecha] form the acronym Elul.
The words forming this acronym come from a verse in the book of Shemot relating to the case of accidental murder:
He who fatally strikes a man shall be put to death.
If he did not lie in ambush but Hashem made it happen, then I will provide you a place to which he can flee.
What is the relevance of this verse of the accidental murderer and the city of refuge to the month of Elul? Many have answered this question simply by comparing the month of Elul to a city of refuge in time. Just as the murderer must flee to a secluded place after committing their crime to repent and ponder their actions, so too we “flee” to Hashem during the month of Elul to repent and consider our behavior over the last year.
There is however an additional element to this connection.
In this week’s Parsha, Shoftim, Moshe Rabeinu mentions again the laws of the cities of refuge. In addition to the laws themselves, there are an additional two verses which relate to the addition of cities of refuge in the future when the land of Israel will expand.
And when the Hashem your G-d enlarges your territory, as He swore to your fathers, and gives you all the land that He promised to give your fathers—
If you faithfully observe all this Instruction that I enjoin upon you this day, to love Hashem your G-d and to walk in His ways at all times—then you shall add three more towns to those three.
According to these verses, in the future, depending on the expansion of the sovereignty of Israel, there will be a necessity to add more cities of refuge in addition to the six already functional. Rashi, quoting the Sifri comments that there will then be a total of nine altogether. In the Sifri itself the issue is in fact a dispute among the Tana’im as to how many cities of refuge will be added, ranging from nine all the way up to fifteen.
The Ramban in his commentary explains that these verses are referring to a time in the future when Am Yisrael will merit keeping the whole of the Torah with a complete heart. A level of devotion to Hashem way beyond what was expected of them to achieve in the times of Yehoshua. Indeed the Rambam quotes these peukim as proof for the coming of the Mashiach :
Anyone who does not believe in him or does not await his coming, denies not only the statements of the other prophets, but those of the Torah and Moses, our teacher. The Torah testified to his coming…Similarly, with regard to the cities of refuge, Deuteronomy 19:8-9 states: ‘When God will expand your borders… you must add three more cities.’ This command was never fulfilled. Surely, God did not give this command in vain.
However, it seems very strange that out of all the mitzvoth in the Torah, the only one that is modified in the utopian times of Mashiach, is the Mitzvah of the Cities of Refuge, by the addition of at least three more cities!
The Minhat Chinuch states that it is a “gezerat hakatuv”, since logically there not only would be no need for additional cities of refuge in the times of Mashiach, even the existing ones would seem unnecessary.
Later commentators explained this peculiarity of extra cities of refuge during the times of Mashiach by differentiating between two different types of redemptions that Am Yisrael could experience. Based on Chazal who say:
Rabbi Alexandri says: Rabbi Yehoshua ben Levi raises a contradiction in a verse addressing God’s commitment to redeem the Jewish people. In the verse: “I the Lord in its time I will hasten it” (Isaiah 60:22), it is written: “In its time,” indicating that there is a designated time for the redemption, and it is written: “I will hasten it,” indicating that there is no set time for the redemption. Rabbi Alexandri explains: If they merit redemption through repentance and good deeds I will hasten the coming of the Messiah. If they do not merit redemption, the coming of the Messiah will be in its designated time.
They suggest that if the Geula will come “in its time”, there will not be a need for any cities of refuge at all. However, if Am Yisrael through their own merit bring the redemption, then the reality does not change drastically, and though there will be many righteous people in that time, there will still be less righteous people as well and it is regarding this scenario the Torah is addressing in these pesukim.
The above however does not concur with the words of the Ramban who, based on careful analysis of the verses, understood them to be referring to a time when all of Am Yisrael are wholeheartedly devoted to Torah and Mitzvot. It also leaves the Rambam’s proof for the coming of the Mashiach from these verses wanting, since they might never be fulfilled.
Perhaps the explanation is actually very straightforward. Living in a very relaxed environment, where all the struggles and challenges are a thing of the past, can actually lead to mindless and habitual behavior. What is the root of the sin of the accidental murderer? It’s not the murder itself, as that was not intended. Their crime is being unaware and thoughtless. This understanding would also explain why according to Chazal based on the verses in our Parsha, the Mitzvah to designate cities of refuge did not apply immediately when Am Yisrael entered Eretz Yisrael. As long as they were involved in the war of conquest there were no cities of refuge. The explanation lies in the understanding that in tense and critical times people do not behave mindlessly. It is precisely when life is easy and effortless that mindlessness creeps in. This is the “danger” of the times of the Mashiach that would necessitate more cities of refuge. 
The Rambam says: “Even though the sounding of the shofar on Rosh HaShanah is a decree, it contains an allusion. It is as if [the shofar’s call] is saying: Wake up you sleepy ones from your sleep and you who slumber, arise. Inspect your deeds, repent, remember your Creator.”
On Rosh Chodesh Elul we start to blow the Shofar. Beyond all the deeper meanings of the shofar, as the Rambam says, it is first and foremost a wakeup call. A wakeup call from the slumber of thoughtlessness, living out of routine and habit without thought.
In conclusion, these words of Rabbi Abraham Joshua Heschel:
It is customary to blame secular science and anti-religious philosophy for the eclipse of religion in modern society. It would be more honest to blame religion for its own defeats. Religion declined not because it was refuted, but because it became irrelevant, dull, oppressive, insipid. When faith is completely replaced by creed, worship by discipline, love by habit; when the crisis of today is ignored because of the splendor of the past; when faith becomes an heirloom rather than a living fountain….— its message becomes meaningless. 
 Shmot 21;12-13.
 See: Likutei Sichot 2;pg 623 ; Me’orot Neriah – Chodesh Elul.
 Devarim 19;8-9.
 Ramban Devarim 19;8.
כי תשמר, כאשר תגיע זכותך שתשמור כל המצוה, לאהבה את השם – אהבה שלימה קיימת לעולם, שיהיה גלוי לפניו שלא תחטא עוד לעולם, אז ירחיב את גבולך ויתן לך כל העמים. והוא לימים אשר אמר (להלן ל ו) ומל ה’ אלהיך את לבבך ואת לבב זרעך, “ולבב זרעך” יורה על כל הימים העתידים לבוא, וכענין שנאמר בקבלה (ירמיה לב לט מ) ונתתי להם לב אחד ודרך אחד ליראה אותי כל הימים לטוב להם ולבניהם אחריהם, וכרתי להם ברית עולם אשר לא אשוב מאחריהם להיטיבי אותם ואת יראתי אתן בלבבם לבלתי סור מעלי. ואז כאשר יכרות להם ברית עולם יבדילו שלש הערים האלה:
 Rambam, Yad Chazakah, Melachim 11;1-2.
 Minchat Chinuch 520;1.
והוא גזירת הכתוב כי מצד הסברא לא יצטרכו לערי מקלט לעתיד לבא כי רק שלום ואמת וטוב יהיה בימי המלך המקוה במהרה בימינו, רק גזה”כ לעשות המצוה הזאת וגזה”כ שיהיה סך הכל תשעה …
 See: Meshech Chochmah, Ha’amek Davar, Torat Moshe (Chatam Sofer) Devarim ibid.
 Talmud Bavli, Sanhedrin 98;a.
 See the following regarding the influence of mindlessness and road accidents:
 Rambam, Yad Chazakah, Teshuvah 3;4..
 Abraham Joshua Heschel, God in Search of Man: A Philosophy of Judaism.