Although I have not shot any Winchester Expert HV ammo in my SR22, I noticed the same phenomenon with the extractor you have described.
I manually loaded a spent .22 shell casing in order to dry fire the weapon. I noticed that upon retracting the slide, the extractor had not grabbed the rim of the casing. Several times I tried cycling the slide manually and it would not pick up the case. As you noticed with your gun, the extractor would not get behind the case to grab the rim. I used a small screwdriver to manually extract it.
Later the same day at the range I had no problems whatever with the extraction of fired casings. In fact, shooting my usual (and now coveted) CCI Minimags the operation of the pistol was flawless.
My thoughts are that you just got ahold of some bad ammo and that your gun is fine.