וַיֹּ֤אמֶר אֱלֹהִים֙ אֶל־אַבְרָהָ֔ם וְאַתָּ֖ה אֶת־בְּרִיתִ֣י תִשְׁמֹ֑ר
אַתָּ֛ה וְזַרְעֲךָ֥ אַֽחֲרֶ֖יךָ לְדֹרֹתָֽם׃
God further said to
Abraham, “As for you, you and your offspring to come throughout the
ages shall keep My covenant." (JPS 2006)
There are various ways to translate "you shall keep" (ESV), but they all convey the idea of a simple imperative. The most common alternative verbs to "keep" seem to be "preserve," "honor," "obey" and "keep faith with." The covenant was an agreement or treaty between two parties. God specifies his promise in the previous verses: he will make Abraham exceedingly fertile, give him the land of Canaan, and nations will come from his descendants.
As to what Abraham must do to uphold his end of the bargain, the central requirement was to circumcise his sons.
10 This is the covenant between me and you and your descendants after
you that you must keep: every male among you shall be circumcised. 11
Circumcise the flesh of your foreskin. That will be the sign of the
covenant between me and you. 12 Throughout the ages, every male among
you, when he is eight days old, shall be circumcised, including
houseborn slaves and those acquired with money from any foreigner who
is not of your descendants.
The OP asks if this covenant was always upheld. The question is controversial with regard to Edomites, Ammonites and Moabites, all of whom descended from Abraham's household. We have more information about the Israelites (descendants of Jacob). Moses definitely did not circumcise his son and almost lost his life as a result (Exodus 4:25). We do not know how carefully the Israelites observed the custom in Egypt but Joshua was told by God to "circumcise the Israelites a second time" (Josh. 5:9) as they entered Canaan. Since the process can hardly be repeated once the foreskin is gone, this seems to imply that some of the Israelites had not upheld the terms of the covenant. Nor do we know how universal the practice was thereafter, although it was certainly the norm.
Under Greek rule, the practice definitely lapsed among Hellenized Jews, to the extent that some even underwent artificial procedures to enable them to participate in athletic programs. (1 Macc. 1:15) Later, Antiochus IV Epiphanes banned circumcision (1 Macc. 1:48) and many Jews complied.
Under Christian rule Jews generally upheld circumcision strictly. In the modern era, however, the practice is no longer universal among secular and Reform Jews.