Puzzling out how to get a needle upgrade in Hollow Knight: Silksong, as well as tracking down Pale Oil for subsequent upgrades, can be a bit of a challenge. In comparison to Hollow Knight, enemies in Silksong are both tankier and deal a lot more damage, so you'll want to upgrade your weapon as soon as possible.
Thankfully, you can do this on the main track, provided you know where to look, though you'll require Pale Oil for any further upgrades to your needle, and this resource proves much harder to find. All that said, I'll explain how to get the initial needle upgrade in Silksong, plus run you through where to find a Pale Oil so you can get the next one as well and finish that Pinmaster's Oil quest.
How to upgrade your needle in Silksong
The good news is that you can get your first needle upgrade for free, but to do so, you'll have to free Bellhart, (which you can find in the far left of Greymoor). This means heading into Shellwood and defeating Sister Splinter to acquire the Cling Grip upgrade so you can wall jump. You'll then need to use it to jump up into the Bellhart tunnels just to the right of her arena and defeat the Widow boss to free Bellhart from cursed thread once and for all.
When this is done, climb the platforms on the left side of town, hop past Relic Seeker Scrounge's bellhome to find Pinmaster Plinney's workshop on the upper right side. Plinney will sharpen your nail for free, giving you the first initial upgrade to your weapon, but he'll also mention that you can upgrade your needle even further with the right item.
Pale Oil location in Silksong
After your initial upgrade, Pinmaster Plinney will give you the Pinmaster's Oil quest, which sees you tracking down Pale Oil in The Citadel. It's important to note that you won't be able to acquire this for quite a while—you'll have to complete Act 1 and the initial sections of Act 2 to access the area, basically, making your way out of the Underworks, climbing the Choral Chambers and defeating the boss there, then descending into the Cogwork Core to gain access to the Whispering Vaults. This is all pretty straightforward and on the main track.
The only part that might give you trouble is getting into the Whispering Vaults via the Cogwork Core. As you descend into the main chamber, you'll want to go down, then right, then up again, completing a platforming puzzle that involves bouncing off a load of moving cogs with your needle.
Once inside the Whispering Vaults, make your way to the main descending chamber and then look for an entrance on the left as you go down. You'll have to head through the upper left entrance in the main room (by bouncing on top of the big enemy who's sleeping at the end of the platform). Inside, you'll have to complete a box-moving puzzle (the solution for which is in the video above) to get your Pale Oil. Bring this back to Plinney to get your second needle upgrade.
Apparently, you can also get a Pale Oil for completing the Great Taste of Pharloom quest that you get given by Loyal Mergwin in the dining room on the route up to the boss at the top of the Choral Chambers. I haven't completed this yet, so I can't confirm, but it's one of the most elaborate quests in the game, meaning it's a much easier option to grab the Pale Oil from the Whispering Vaults instead. I'll add details about that second Pale Oil once I've finished the quest.
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