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The way the midrash (Shemot Rabba 19:5) connects Korban Pesach and milah may clarify somewhat. The people were reluctant to perform milah but, according to the midrash’s first version, when they found out it was a prerequisite for taking part in the Korban Pesach, they became willing to do it. According to the second version, it was not until the preparations for the Korban Pesach began and the smell enticed them to beg to take part that Moshe was able to get them to perform milah.
That still does not explain why the connection between the two was not revealed earlier. The midrash mentions the significance of the intermingling of the blood of the milah and that of the Pesach. Thus, the fact that the milah was done at the last moment might have had some positive value.
However, it is likely that Hashem would have preferred for the people to fulfill their sacred obligation of milah well in advance without prodding. Indeed, the midrash praises the Tribe of Levi for having been careful about the matter throughout the years of servitude. Bnei Yisrael, in their downtrodden state, were not in the practice of performing any mitzvot. They had enough trouble following the commandments that Pharaoh imposed upon them. Why should they follow the practices their fathers related from a G-d who had allowed them to be in a wretched situation? Only when the final steps of redemption were palpable, represented by the Korban Pesach, were they willing to put in their bodies a sign of servitude to Hashem instead of to Pharaoh. According to the midrash’s second version, it was not even enough to know that this was to happen. Rather, they had to "smell in the air," literally and figuratively, the festivity of freedom in order to do so.
Since ancient times, we have never forgotten the status of free men and the related obligation of milah that encourages us to give ourselves over to Hashem. May the stages of redemption and the "smell" of hopefully imminent further redemption encourage more of us to intensify our service of Hashem.
Various Rabbis
Various Rabbis including those of of Yeshivat Bet El, such as Rabbi Chaim Katz, Rabbi Binyamin Bamberger and Rabbi Yitzchak Greenblat and others.
Moreshet Shaul Moreshet Shaul: A Crown and its Scepter – part II
Based on Siach Shaul, Pirkei Machshava V’Hadracha p. 294-5
Rabbis in Midrash
Lessons
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Hosha'ana Rabba FLYDUBAI & HOSHANA RABBA- ANI VAHU HOSHIA NA- I & HIM SAVE US
"Ani vaHu Hoshia Na", "I and Him, Save Us". We don't just pray to Him, but we also pray to and for ourselves that we should emulate and educate our children to have that instinctive altruism with which He created the world. President Trump seemed amused about Yaniv Hayon, our PLUMBER who confidently worked with G-d like Superman (he learned from a pilot on a TV show!) to save 174 lives on the Dubai hijacking, but we in Israel are totally accustomed already 78 years to our plumbers, teachers, garbage-men, rabbis, farmers & doctors being Hashem's shlichim! This is what Zionism is about.
Moreshet Shaul Hashem Is your Shadow – part I
Based on Siach Shaul, Pirkei Machshava V’Hadracha p. 420 – an address from 1941
P'ninat Mishpat A Non-Contractor in Changing Times – part I
(based on ruling 85128 of the Eretz Hemdah-Gazit Rabbinical Courts)
Moreshet Shaul Our King on Rosh Hashana, Our Father on Yom Kippur.
Based on Aroch Siach, p. 221 (Rav Shaul Yisraeli)
