In the beginning, after all of my noob reading, I initially started drawing with 18ga and pinning with 25ga for my first cycle with pins. I had no problems for a long time, so I kept using the same consumables until I ran into stoppers that were more easily chewed up.
18ga wasn't the worst, but over time I definitely saw a few tiny rubber chunks. I searched for this problem and found that not all stoppers are equal, but some people just mitigate this by using smaller needles.
I re-filtered that vial and tried drawing with 25ga. I had no problem with that, and it's what I use for drawing now.
Could your vial be under a lot of vacuum, making it more difficult to draw? Maybe you need a temporary vent to help equalize. Some of my peptides have been under incredible vacuum, where all bac water was pulled through a 25ga needle quickly upon insertion of the needle - I didn't even have to push the plunger, the vacuum sucked it down!
Are you pulling the plunger down farther than the amount you are trying to draw, to create more vacuum?
In the grand scheme of things I'm still relatively new to this, but Test Prop in MCT flows very easily for me at room temperature. And warming the oil makes it flow very quickly, even through a 0.22μm filter.
If these are very simple solutions that you have already tried, I apologize and hope you figure it out quickly. Re-filtering gear isn't the worst, but I'm sure we would all rather be doing other things.