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Our DM cast web on us, and we were all asked to make saving throws immediately. He said, "Otherwise you’re all like Schroedinger's Cats waiting to see if you’ve been caught or not" (which affects attacks on us).

However, those that weren't restrained had to make saving throws again at the start of our turns (no problem with that since the rules clearly specify).

It is difficult to argue with our DM that we shouldn’t make saving throws when it is first cast.

When should we make our first saving throw?

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At the start of your turn

According to the official spell description for web:

Each creature that starts its turn in the webs or that enters them during its turn must make a Dexterity saving throw.

(Emphasis Mine)

The spell, when cast, fills the entire area at once (unless described otherwise by the DM). That means each of you has to make a Dexterity Saving Throw on the beginning of your respective first turns after the spell is cast, becoming restrained if the save is failed.

Just a quick note: Usually the DM will ask you to roll the Saving Throw when the spell is cast to save some time, instead of asking each individual on their turn.

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On your turn

The spell web states (emphasis mine):

Each creature that starts its turn in the webs or that enters them during its turn must make a Dexterity saving throw.

Let's assume a wizard "Caster" and another creature "Target". Under typical circumstances, web will be cast on Caster's turn. At that point, it isn't Target's turn, so they do not yet make a save. Once Target's turn begins, they save if they are in the web, or if they enter the web on their turn.

Even if Caster used Ready to release the spell in Target's space during Target's turn, they still would not (necessarily) have to save. Target did not enter the area, the area was placed around them. If Target does not move, they do not have to make the save until the start of their next turn.

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Your saving-throw against Web occurs on your turn. You should not have made a roll when the Web was released.

Your saving-throw against Web (PHB 287-288) occurs on each of your turns, not on other characters' turns.

Each creature that starts its turn in the webs or that enters them during its turn must make a Dexterity saving throw. On a failed save, the creature is restrained as long as it remains in the webs or until it breaks free.

A creature restrained by the webs can use its action to make a Strength check against your spell save DC. If it succeeds, it is no longer restrained.

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