I just checked the direct OPRA feed and at 1:55 pm ET yesterday, the market was [0.00 - 1.00] (no bid) for that strike. It explains why you didn't get filled and it shows that there were no stale quote on the market. Possibly a glitch on the IB side.
1) Right..no one is trading my fills just falls from the sky. 2) I have had 2 TWS open every day for the past few years. It works 98% of the time, it's only an annoyance that should be fixed by IB. 3) Thanks, I will try this it next time. Thank you for your clues for clearing my confusion.