I have removed some old drywall anchors and want to fill in all the holes.

The tricky part is that some of the holes are in exterior walls where there is a vapor barrier (plastic sheeting) outside the drywall, and there are holes through it after the anchors.

Do I have to try to press in silicone or something similar first and then fill, or can I just fill and be happy?

The filler I normally use is regular sand filler.
 
Got advice to push silicone into the holes, then perhaps the question is what type of silicone, regular/Wetroom or outdoor silicone...
 
It became polyurethane foam in the holes, hopefully, it will suffice as a vapor barrier.
 
I wouldn't use silicone considering it's a nightmare if you want to paint or similar. I've chosen latex sealant around window frames and probably done the same in the wall.
 
The idea was not to completely fill the holes with silicone but first to press in silicone so that it sealed against the existing vapor barrier (meaning that the hole in the vapor barrier is covered) and then fill the rest of the hole with putty.

Now, as mentioned, it ended up being foam sealant, so now what's left is to carve away the excess, etc., so I can fill the last part with putty. Hopefully, the foam sealant will suffice as a vapor barrier.
 
Seriously. Is a vapor barrier really so tight that a few screw holes would make any difference? If you don't have crossed inner studs, the vapor barrier is likely full of holes anyway due to all the electrical boxes?
 
Agree, when has a vapor barrier actually become obsolete? Just look around electrical/tele sockets, how many constructions are there where the manufacturers' instructions have not been followed (tape, etc.).
The vapor barrier is there to prevent air (vapor) from reaching colder areas and to prevent moisture from condensing inside the wall, but it doesn't happen arbitrarily, it happens where the air can pass. If you have a good vapor barrier, you should maintain it.
 
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