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PKHeX needs contributions to refine the Legality checks in the Wild Area. Pokemon that spawn outside of the grass are considered Static Encounters (see Kaph's long list here), and we need data for the Nests too. If you have legitimately caught Pokemon from the Wild Area that is being flagged as "Invalid: Unable to match an encounter from origin game", please contribute your .pk8 files either by attaching them to this thread or by sending a Private Message. Alternatively, if you are a developer, you can contribute the `Species` and `Met_Location` of the Pokemon. Or just directly contribute to the project on GitHub. You can track the progress on GitHub here: https://github.com/kwsch/PKHeX/blob/master/PKHeX.Core/Legality/Encounters/Data/Encounters8.cs

You can't. There's no official way to transfer Pokemon from previous generations until Pokemon Home is released sometime next year. So anything from previous generations is illegal currently.

Now that I'm done school for the semester I figured that I would finish conducting tests to try and fill in the missing data in the structure, as well update the data that I was unsure about. Therefore, the original post has been updated to reflect my most recent tests and now I feel relatively certain that the presented data is accurate. I most likely will not be making any changes to the above table or carry out further tests on this subject.