I think it happens. If you listen to the Arturia emulations, they all have a bit of a boxy sound to them that can be heard despite character differences in all of them. Even OB-Xa V has it.
Another thing that happens is preset style. You can hear Howard Scarr all over every single U-He synth, though his stuff is great and pretty wide ranging. Listen to Tone2 plugins though. I swear it’s as if they try to replicate the same set of presets over and over again. I don’t think I could pick any one of their synths out in a blind test, but when you dig into them you can start discerning differences, though it’s still clear they’re made by the same company.