1

If some act is challenged as unconstitutional and another act is also challenged as unconstitutional, and the supposed unconstitutional actions were executed by the same defendant against the same plaintiff, and the actions are not dependent on each other and took place at different times, can both of the alleged unconstitutional actions be challenged in the same case or do they have to be raised separately?

2

In most cases, yes. This is called permissive joinder, and it is permitted under Rule 18(a) of the Federal Rules of Civil Procedure:

A party asserting a claim, counterclaim, crossclaim, or third-party claim may join, as independent or alternative claims, as many claims as it has against an opposing party.

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