Learn Hardcore Filipino: Magpagupit din siguro si Maria sa lungsod kapag may oras na siya. - Maria will probably also get a haircut in the city when she has time.

gupit – the root; it can mean a cut (especially haircut) or to cut.
maggupit / magupit – to do the cutting yourself (e.g., to cut something, or for a hairdresser, to cut someone’s hair).
magpagupit – to have someone cut your hair; to get a haircut (causative: you cause someone else to cut).

So in this sentence, magpagupit means Maria will have her hair cut (by someone), not that she will be the one cutting someone else’s hair. The prefix magpa- often carries the idea to have something done / to get something done to oneself.

Why do we say si Maria and not just Maria? What does si do?

Si is the personal name marker for singular, specific people in Filipino. It shows that Maria is the subject/topic of the sentence.

si Maria – marks Maria (a specific person) as the subject.
Without si, Maria would sound ungrammatical in this position.

If you replaced her name with a pronoun, you would say siya, not si siya. You use si only directly before a proper name (or sometimes titles used like names, e.g. si Dok).

Why is the verb first: Magpagupit … si Maria instead of Si Maria ay magpagupit …?

The default word order in Filipino is often verb–subject–(other elements):

Magpagupit din siguro si Maria sa lungsod… (verb first)

This is the most natural, conversational order.

You can say Si Maria ay magpagupit din siguro sa lungsod… with ay after the subject, but that sounds more formal or bookish. In everyday speech, people usually put the verb first.

What tense or aspect is magpagupit here? How does it end up meaning “will probably get a haircut”?

In Filipino, mag- + root in this form is contemplated / future aspect (uncompleted action):

magpagupit – will have a haircut / is going to get a haircut (not yet done).

The sense of “probably” comes from siguro, not from the verb form itself. So:

Magpagupit si Maria… – Maria will get a haircut.
Magpagupit siguro si Maria… – Maria will probably get a haircut.

The verb form shows it’s not yet happening; context + siguro make it future and uncertain/probable.

What is the role of din and siguro? Can I say siguro din instead of din siguro, or move them around?

Both din and siguro are particles:

din – also, too.
siguro – probably, maybe (expresses uncertainty or supposition).

In normal speech, Filipino enclitic particles like din tend to come right after the first stressed word/phrase of the clause, and they also have a preferred internal order. In this sentence:

Magpagupit din siguro si Maria…

is more natural than Magpagupit siguro din si Maria…, though that might still be understood.

You could also move both particles with some change in emphasis, for example:

Si Maria din siguro ay magpagupit sa lungsod… (more formal and with focus on Maria also, probably).

But the original order (magpagupit din siguro) is natural and colloquial.

What does sa lungsod add? Is it just “in the city”? Could I say sa siyudad or sa city instead?

Yes, sa lungsod means “in the city” or “to the city” (depending on context; here it’s like in the city / in town as the place of the haircut).

lungsod – city (often feels a bit more formal or standard).
siyudad – also “city”, borrowed from Spanish ciudad. Common in many regions.
sa city – mixing English; widely understood and often used in casual speech.

All of these can work in everyday Filipino. The nuance is more about style and register; sa lungsod feels more standard/neutral Filipino, sa siyudad is also common, and sa city is more colloquial or “Taglish”.

What does kapag may oras na siya literally mean, and why do we need na there?

Literally:

kapag – when / whenever
may oras – has time / there is time
na – already / by then
siya – she / he

So, kapag may oras na siya is roughly:

“when she already has time”
or more naturally in English: “when she has time” / “once she has time”.

The na marks a change of state: the time when she goes from not having time → to having time. It makes the clause sound more natural and complete in Filipino, similar to English “once / by the time she has time”.

You could say kapag may oras siya, and that’s still correct, but kapag may oras na siya is a very common, natural way to say when she (finally) has time.

What is the difference between kapag and kung here? Could I say kung may oras na siya instead?

Both kapag and kung can translate as “when” in English, but there’s a nuance:

kapag – usually “when(ever)” for conditions that are expected or more neutral.
kung – often “if” (conditional), but can also be “when” in some contexts.

In this sentence, kapag may oras na siya suggests:

“when she has time (and we expect that time to come at some point)”.

If you say kung may oras na siya, it leans a bit more toward:

“if she has time (assuming she might or might not)”.

Both can be understood, but kapag is more natural here because we’re talking about a time that is expected to arrive eventually.

Do we need to mention buhok (hair), like magpagupit ng buhok? How do we know it’s a haircut?

In everyday Filipino, magpagupit by itself is usually understood as “to get a haircut”, because that’s the most common thing people “have cut” on themselves.

You can say:

Magpagupit ng buhok si Maria… – Maria will have her hair cut.
Magpapagupit ng buhok si Maria… – same idea, with a more clearly marked future aspect (magpapagupit).

But it’s not required. Context and common usage allow magpagupit alone to mean get a haircut, unless you specify a different object.

Can I drop siya in kapag may oras na siya and just say kapag may oras na?

Yes, in many real-life conversations, speakers might say:

Magpagupit din siguro si Maria sa lungsod kapag may oras na.

The subject (Maria / she) is already clear from the main clause, so siya can be omitted and understood from context.

kapag may oras na siya – explicitly “when she has time”.
kapag may oras na – “when (she) has time”, with she implied.

Both are grammatically fine; including siya is just a bit more explicit.

What’s the difference between using both din and siguro versus using just one of them?

Each particle adds its own nuance:

din – also / too, connects this action to something previously mentioned (maybe someone else got a haircut, or Maria did something similar before).
siguro – probably / maybe, softens the statement; the speaker is not 100% sure.

So:

Magpagupit si Maria sa lungsod… – neutral statement: Maria will get a haircut.
Magpagupit din si Maria sa lungsod… – Maria will also get a haircut.
Magpagupit siguro si Maria sa lungsod… – Maria will probably get a haircut.
Magpagupit din siguro si Maria sa lungsod… – Maria will probably also get a haircut (both “also” and “probably” are active).

Using both is purely about meaning and tone; it doesn’t change the grammar, just adds the ideas of also and probably at the same time.