I have also read that when assigned the last roll over of the premium collected is factored into the cost basis.
Found this on another forum "For short puts that are assigned, the cost basis of the shares purchased is reduced by the amount of premium received. For short calls that are assigned, the total proceeds from selling the stock are increased by the amount of premium received. For short options contracts that have expired without assignment, the premium received is reported under Closed Positions."
Your broker may not be answering your question. They may be answering a different question. When they say the premium is not included in the cost basis, they may be giving you an accurate description of what you are seeing in the data displayed in your account right now, on your positions page, or whatever you are looking at. That's not the same as telling you how to report the transaction on your tax form, and it's not the same as telling you what data will appear on your Form 1099-B early next year. The IRS instructions are very clear.
I agree on how you are saying how it will appear on my 1099-B, however I'm not seeing any of it on my history. Meaning in the realized profit / losses report area there is zero sign of the trade even showing up, in my history all it shows is my assignment that I paid for the trade ... I sold the puts in 2024, I rolled it over a handful of times throughout october november and December and took assignment in January 2025. So now my question is on the 1099-B will I see the premiums obtained for my tax year 2024 or does not all this settle until the shares are actually sold off ?
The premiums you collected should not appear on the 1099 for 2024, because you were still holding the shares at the end of the year. If those premiums do appear on the 1099, then you need to look at it very carefully. It may be information only, and it may not actually be in a box that will be reported on your tax return. If you find that the premiums are in fact showing up as proceeds of a sale, then you may need to enter an adjustment. Depends on exactly how it is reported. If it is reported as proceeds of a sale, then the put itself must have a basis. Normally it would be zero, because you wrote the put. So you could enter an adjustment and indicate that the basis on the 1099 is incorrect, and that the correct basis is the same as the premium, so there would be no gain from the sale of the put. But this is pretty speculative. It probably won't be on there at all. As for the basis of the stock you bought when the put was assigned, the broker does not have to determine the basis for tax purposes until they issue the 1099, i.e., until after the stock has been sold. Apart from the put premium, there are other things that could change the basis between now and whenever you sell the stock. For example, a stock split or a merger or a spinoff.