I am assuming you have added the desired via to the constraint manager physical tab so it can be used? When adding the connection you need to make sure the find filter has pins, shapes, and whatever else you want to detect on checked. You should be able to route from any arbitrary object and drop a via. If you are getting DRCs that's normal (another topic tho...). If you are getting some other DRC that is preventing the via to touch the pin then drop it and move it with "allow DRC" and hug/shove turned off. If still stuck you can either post up the symbol here or PM it for a look. Or even a screen shot of what's happening.
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