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Sir,
I would suggest stripping the bolt, and checking the ejector and the hole it travels in for burrs and other irregularities.
Look to see if the end of it appears to be mushroomed or deformed. (That is a bad thing)
Check the spring to be sure it is traveling properly, and is not broken or deformed.
If you are not capable of doing that yourself, take it to a GOOD gunsmith, and have him go through it.
The plunger type ejectors common to the post '64 (pushfeed) Winchesters and Remington 700 type weapons are prone to problems like you are experiencing, and are sometimes either too soft or have other poor finish features that can cause malfunctions. Ice, grit, powder fouling and brass shavings can all cause malfunctions in these ejector types.
They can get into the channel that the plunger travels in, and bind it up.
While you are at it, check the bolt face and extractor for burrs, dirt, grit, machined chips that were left in by mistake, etc.
These can cause the rapid accumulation of undesirable crud in that area.
Also, if the ammo cartridge was a particularly soft brass alloy, this could cause problems due to the brass deforming into the ejector and shaving off.
Good luck.
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