Passage
Ascalon shall see, and shall fear, and Gaza, and shall be very sorrowful: and Accaron, because her hope is confounded: and the king shall perish from Gaza, and Ascalon shall not be inhabited.
Zechariah 9:5 (DRB)
Nearby Context
Zechariah 9:3 And Tyre hath built herself a strong hold, and heaped together silver as earth, and gold as the mire of the streets.
Zechariah 9:4 Behold the Lord shall possess her, and shall strike her strength in the sea, and she shall be devoured with fire.
Zechariah 9:5 Ascalon shall see, and shall fear, and Gaza, and shall be very sorrowful: and Accaron, because her hope is confounded: and the king shall perish from Gaza, and Ascalon shall not be inhabited.
Zechariah 9:6 And the divider shall sit in Azotus, and I will destroy the pride of the Philistines.
Zechariah 9:7 And I will take away his blood out of his mouth, and his abominations from between his teeth: and even he shall be left to our God, and he shall be as a governor in Juda, and Accaron as a Jebusite.
Study Lenses
The verse centers on "ascalon", "shall", "fear", "gaza", "very", and "sorrowful". It is saying that the verse draws attention to "ascalon" and "shall", so its meaning should be read from those terms before moving to application.
The nearby context moves from verse 4's "Behold the Lord shall possess her and..." into verse 6's "And the divider shall sit in Azotus...", so "ascalon" and "shall" belong inside that flow. In Zechariah context, the local focus is covenant, worship, and faithfulness.
A plain takeaway is to answer the verse's own emphasis on "ascalon" and "shall" with trust shaped by these words, not by a vague optimism outside the passage.