I've been tinkering with options for 20+ years and have been assigned countless times. But believe it or not, I have never exercised a position. So let's treat this like a newbie question I trade a variety of ratio calendars and strangles for earnings. Two weeks ago, I had a leftover position from a reverse calendar ratio straddle where the bid of the long near month call was 60 cents or so under parity. Yep, highway robbery! That 60 cts was a chunk of profit to give up. The particulars were something like: $37.40 - 37.45 stock 1.85 - 2.45 Mar 35 call (+4) 3.60 - 3.70 Apr 35 call (-5) Closing the options at the respective B/A's would have been at a debit of $11.10 (+4 * 1.85 -5 * 3.70) Am I missing something or wouldn't it have been a better idea to exercise the 4 long Mar 35 calls to obtain the stock for 35 and simultaneously shorting 400 shares at 37.40 netting 9.60 (+4 * 2.40) and covering the 5 short Apr 35 calls @ 3.70 (-18.50) thereby having a total debit of only $8.90 ? ($2.20 better) TIA.