Is threading a male dupont wire through a PCB pin-hole and soldering it advisable?

I've been having some trouble attempting to solder this board here, more specifically I bought a pre-soldered OLED screen, some dupont wires, and soldered the ESP32-S3 rail on myself. I stripped the dupont wires and twisted, then tinned them before soldering onto the potentiometers while still then connecting to the rail using a one-side stripped, one side female dupont wire setup.

However, this method was unreliable and kept breaking. My dilemma is that, I'd like to buy solid wires (and actually just did) to solder directly to the PCB, however the OLED screen has the aforementioned rails that I don't feel comfortable attempting to remove. Would it be a good idea to remove the esp32 rails and connect the female dupont to the screen, then thread the male end through the esp32 pin-holes and solder it? I'm still very inexperienced with soldering, but I feel as though buying more dupont wires to strip and attempt again seems like a bad idea, as not only were they breaking but before it broke, the serial output was reading as though there was no input (e.g. values were inconsistent, but otherwise all was working).

I'd like to avoid attempting to manually add female / male dupont connectors to wires or crimping as being quite honest, I'm fairly frustrated so far with this and feel doing so would only worsen things. Any help is greatly appreciated.

Q: (title)
A: yes

I assume that "rail" means "header pins"?

Is there a reason why you don't use female-female duPont cables for connection between the Nano ESP32 header pins and the screen header pins?

Based on your description of wires breaking I guess you have too much movement between components.

That is correct regarding the rail / header pins.

For the female-female connection, I was under the assumption that soldering solid-wires directly to the board similarly to the video I've based my project on would be more secure and allow for longer wiring than the dupont cables.

While yes, the components are moving more than they should given that I do not have a case yet, even when perfectly still values were returning as though the connection was improper before even breaking, which makes me what I was doing previously would not be a good idea to try again.

Perhaps the way you did it is the problem. The Dupont wires have very few strands so sharp bends leads to very sharp bends in each strand. The alloy of copper may also make them more susceptible to work hardening.
IF you did not use leaded solder, then the point where the wire bends is at the point where the solder ends. With leaded solder, the thin solder will also bend and keep the copper from work hardening.
Tinning other than just the tip of the wire will cause bending problems. The insulation of the Dupont wires is relatively thick and stops sharp bends. Keep the insulation as close to the circuit board as possible.
As a final fix, use electronic grade RTV to reinforce the wires at the circuit board connection.

Any soldered joint of a flexible wire and a connection generates a point of weakness at the soldered point. If this is then flexed it is likely to snap at the joint. The way round this problem is to apply some strain relief to prevent the flexing at the soldered point.

One way to provide this is to use a small dab of hot melt glue to prevent the joint flexing.

By the way, you have posted in the Official Hardware Nano ESP32 section. Is that what you are using, or is it some "other type" of knock off board from China?

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