TLDR: Try it, it’s super helpful especially for reconciliation. You can also do it on iOS (can’t say anything about Android):

• File export: if your bank doesn’t support QFX, OFX, QIF, or CSV (YNAB info page), you can export a QIF file from e.g. Banking4 for iOS (add your bank account, then under menu → tools → data export). If you only have a CSV, you can use this tool to prepare it.
• File import: Save the file to files and then drag&drop it to the website. For me, it worked best with the free Zoomable App.
• Everything else can be done in the YNAB App

That sounds like a lot, but it’s actually pretty simple. Definitely faster than doing it manually.

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I’ve been using YNAB since 2014, but never used the file based import since it always struck me as too cumbersome. Maybe I was also just misunderstanding the feature, thinking since I’m writing down all transactions I don’t need to import them.

But it’s actually extremely helpful for reconciling. I used to go through every single transaction in my bank account to then find it in my YNAB transactions, which was really tedious if there was even just a small mistake somewhere (I was only doing it once a month). And I never had a full month without any mistakes.

Another reason that kept me from using it, was the feature only being available on desktop, but I’ve since found a way to do it on my phone (iOS). YNAB should really make it possible to import these files directly in the app, but for now I have the workaround as mentioned above.