Just my two cents worth. The safety chain may be slower but I don't believe it is your primary problem from the pictures.
The safety tie straps mostly come into play at the tip of the bar to prevent kickback. They are well below the depth gauges as shown in the photos which do appear to be too high.
As rmh3481 mentioned, looks to me like you have used the wrong size file and are cutting more with the top of the tooth than the side - the part that creates your kerf and keeps the cut open. As you first stated, it seemed like the wood is swelling up in the cut. Since Pine is a softer wood, the chain may be tearing the grain along the sides of the cut rather than shearing it as it would with harder grain like oak or locust.
Since you mentioned this also happened with a fairly new chain, you should have the bar slot checked for wear. If worn, the tooth can also lean inward and not cut an adequate kerf. There have been other threads like this, usually comes down to getting a good bar and properly sharpened chain.
The safety tie straps mostly come into play at the tip of the bar to prevent kickback. They are well below the depth gauges as shown in the photos which do appear to be too high.
As rmh3481 mentioned, looks to me like you have used the wrong size file and are cutting more with the top of the tooth than the side - the part that creates your kerf and keeps the cut open. As you first stated, it seemed like the wood is swelling up in the cut. Since Pine is a softer wood, the chain may be tearing the grain along the sides of the cut rather than shearing it as it would with harder grain like oak or locust.
Since you mentioned this also happened with a fairly new chain, you should have the bar slot checked for wear. If worn, the tooth can also lean inward and not cut an adequate kerf. There have been other threads like this, usually comes down to getting a good bar and properly sharpened chain.