I have been using TT Premier for many years (desktop version). I started trading stock options in 2013 and have been using the 1099B import feature w/o trouble until the 2023 tax-year, which marked the transition from E-Trade reporting things to Morgan Stanley. When I did the import last year, I had to manually enter a value of $0 as the basis for all of the sold options on the MS 1099B - around 170 entries if I recall correctly. I was hopeful that this was somehow a one-time glitch caused by the ownership transition.
Unfortunately, the import this year required me to manually review some 370 transactions b/c the basis field was null. I contacted E-Trade about the problem and was informed that MS has a broader interpretation of which option contracts qualify as section 1256 contracts. All of my sold options contracts are now being classified as section 1256 contracts and so the reporting is different. For example, the date the contract was sold is not listed. Instead, the expiration/closure date is duplicated. The paper 1099B correctly shows a basis of $0 for these trades but I have no idea what is in the import file that TT uses.
I resolved the issue only by entering a basis value of $0 for all 370 trades (many mouse-clicks and several hours of mindless effort). I didn't fix the date problem. That satisfies TT's sanity check. But here's the deal: I don't want to have to do that every year going forward. I didn't have to do it all before the MS transition. I shouldn't have to do it now.
