'When you cast a spell' refers to the timing of the use of Careful Spellis unclear, but we can refer to notHeightened Spell the forced savefor context
Multiple possible meanings
The "whenIt is not immediately obvious what 'when you cast a spell" obviously sets the timing condition for the election ofspell' means here, because the phrase is used to mean Careful Spell. That must be chosen, or not, at that timedifferent things at different places in the rules.
What is unclear is whether the "whenSometimes 'when you cast a spell" timing condition also refers tospell' sets up things that can only happen at the "that forces other creaturestime of spell casting, like choosing who is permitted to makeenter and leave a saving throw"Tiny Hut.
Unfortunately If this was the case here, therethen since no saves are two possible waysmade for Web at the time of its casting, Careful Spell could not be used to interpret this:protect allies.
[WhenBut sometimes 'when you cast a spell]
(that forces other creatures to makespell' sets up things that happen for the entire duration of a saving throw)spell,
[you can like when you upcast a Wall of Fire, and the additional damage applies over every round the spell is in effect. If this was the case here, then Careful Spell could protect some of those creaturesyour allies from any saving throw imposed by Web for the spell's full force]duration of the spell.
could mean
At the point in time in which you cast a certain kind of spell (the kind that forces a saving throw), then you can use your Careful Spell to protect those creatures from all future saving throws caused by the force of the spell.
ThatUnfortunately, since the phrase itself is used in different ways, you must electthere is no way to useknow for certain which way it is intended to be used in Careful Spell atbased on a reading of the timetext of spell casting, but once elected, it will protect a creature for all saves against that particular spellCareful Spell itself.
However,
[When]
[you cast Either interpretation produces a spellresult that forces other creatures to make a saving throw]seems reasonable,
[you can protect some of those creatures from as the spell's full force]
could also meanvarying answers to this question attest.
At the point in time in which you cast a spell and that spell immediately forces a saving throw, then you can use Careful Spell to protect a creature from that immediate saving throw, only.
I believe that the timing condition applies toHowever, we can compare Careful Spell, only, and not to other metamagic features that use the saves, for two reasons: grammarsame phrasing and the wording of a similar metamagic featuredo not have as ambiguous an interpretation.
Comparison to Heightened Spell
Comparison to Heightened Spell
Heightened Spell actually says (emphasisemphases mine):
Why specifically call out its first saving throwIf, when you could simply sayin the context of metamagic features, "When'when you Cast a Spell that forces a creature to makecast a saving throwspell' was meant to resist its Effects, you can spend 3 sorcery pointsapply to give one target of the spell disadvantage on that saving throw."
If the "when you cast" clause meanteffects that we should count only saving throws made onlast for just the turncasting of the spell was castitself, then the only reasonthere would be no need to indicatespecifically call out its effect as being on the first saving throw only, since it would already be for spells on which more than one save is made by a target on the turn the spell is cast.
On the sorcerer spell list I am counting just one1 spellunderstood that calls for multiple saves on the turn it is cast, Earthquake, and then only if a target is also concentratingsave made at the time.
To me, it strains credulity to believe that the 'first saving throw' language was deliberately added to the Heightened Spell description so as to cover the effects of just one spell a sorcerer can first get at 15th levelcasting would apply.
On the other hand, it seems very reasonable to me that the 'first saving throw'effect of Heightened Spell is meant to applyexplicitly being restricted to just the first saving throw provoked by sorcerer spells that provokecan lead to multiple saves over multiples turns or on subsequent turns,multiples turns such as1 Blindness/Deafness, Gust of Wind, Hold Person, and Web all starting at 3rd level, and later on Fear, Sleet Storm, Slow, Stinking Cloud, Confusion, Cloudkill, Hold Monster, Insect Plague, Delayed Blast Fireball, Incendiary Cloud, and Power Word Stun.
"When you cast" inIf Heightened Spell clearly indicates saves madecontains language that explicitly restricts its use to the first save and on turns after the turn in which the spell is castCareful Spell. Unless you want to argue that the phrase has different meanings for the different metamagic abilities does not, "when you cast" should then also allowit stands to reason that Careful Spell is meant to beapply to any and all saves provoked by the spell it is used forwith, so long as the phrase 'when you cast a spell' is used consistently between the two metamagic features. And while 'when you cast a spell' does mean different things in different contexts, I can think of no good reason why it would mean different things in two examples of the same context, that is, two metamagic features that affect creature saves on subsequent turnsagainst the spells they are used with.
It seems to me that the most logical inference is that Careful Spell affects all saves. Thus, one may protect an ally from Web by using Careful Spell, even when the save is not made on the same turn the spell is cast, and the metamagic feature is usedeven if multiple saves are made over multiple rounds.
Grammar: the feature is describing what kind of spell it works on
The descriptive clause "that forces other creatures to make a saving throw" is describing what kind of spell you can use Careful Spell on. You cannot use it on spells which do not force a saving throw (for example, firebolt, or mage hand).
If, instead of describing the class of spell, the saving throw clause was describing the timing condition required, we would also have to take it literally when it says "forces other creatures to make a saving throw". That is, if making the save was required at the the time of casting, that save would have to be made by more than one creature; you could not use Careful Spell on a spell that forced a save for a single creature only at the time of spell-casting.
1I am currently working from the SRD and realize that there may be other spells in both categories. However, I doubt there are many more that provoke two saves for the same creature on the same turn the spell is cast.