There is a din d'oraysa of lo tasgir eved el adonav that prevents anyone from sending an eved who flees to Er"Y back to chu"l, but some Rishonim go a step further and say that the eved is automatically free. Why should this be so? The difference between Eretz Yisrael and chu"l is that Er"Y is sustained by Hashem directly, while parnasa in chu"l comes through the intermediary of angels. Avnei Nezer (Y.D. 454) explains that since the responsibility for the support of an eved lies with his master, so long as the master is in chu"l, the eved is still chained to the chu"l status of mezonos through the intermediary of angels. This is effectively 'lo tasgir.' It's only once the eved is free and can enjoy mezonos of Er"Y, support directly from Hashem, that he is truly a ben Eretz Yisrael.
The Av"N's teshuvah is important l'halacha with respect to the question of whether someone who relies on charity or support from chu"l is really fulfilling the mitzvah of yishuv Er"Y, but what's important for us is that he ties this whole discussion back to inyanei Pesach. The idea of achilas matzah and korban pesach is that responsibility for our parnasa switched from Pharoah to Hashem. The Torah calls achilas k.p an "avodah" because it transforms us from avdei Phraoah into 'avdei Hashem.'
Even though achilas pesach itself is not m'akeiv, a person has to be ra'uy to do achilah at the time of zerikas ha'dam because it is this capacity to receive our sustenance from Hashem which marks our freedom from bondage.
(We have similar concepts that come up elsewhere, e.g. the idea of children who are "someich al shulchan avi'hem" being connected to his home; the idea of "makom pita" as opposed to "makom linah" defining a person's residence; the idea of chiyuv mezonos connecting a wife to her husband's home.)
Shem m'Shmuel extends this same idea to milah. The chosam bris, beyond just being a mitzvah, is a siman of our avdus to Hashem. Tosfos (Pes 28) asks why we need a chiddush din to tell us that an areil must eat matzah. Peshita -- he is patur from korban pesach, but the Torah never says he is patur from matzah?! Sm"S answers that one might have had a hava amina that the lack of milah is not just a ptur from the mitzvah of k.p., but is a siman of a chisaron in the status of eved Hashem. Kah mashma lan that the areil is still chayav.
"Ha lachma anya di achlu avhasana b'ara d'Mitzrayim." Abarbanel learns that matzah is slave food; the Egyptians fed it to Bn"Y because it is simple, low budget food. Maharal disagrees and explains that the hagadah is referring to the matzah Hashem commanded us to eat on Pesach night. Sm"S wants to have his cake (or maztah) and eat it too. Matzah is indeed a food of slaves, but on seder night it becomes a symbol of our freedom because our freedom is avdus -- avdus to Hashem instead of to Pharoah.
Perhaps this explains (see previous post for the Chasam Sofer's hesber of the same point) the connection between the beginning of "ha lachma anya" and the end, "l'shana haba'ah b'ar'ah d'Yisrael." Since we are now eating mi'shulchan gavoha, proving that we are avdei Hashem, m'meila our sustenance should come directly from Him, which can happen only in Eretz Yisrael.
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