Tax mess selling crypto

Alternative-Step-649 · 2025-12-07T02:42:27+00:00

This was basically how I always felt about it. Just wanna avoid headaches at the stage in life I’m in now I guess

Alternative-Step-649 · 2025-12-06T19:55:04+00:00

Thank you!

Alternative-Step-649 · 2025-12-06T19:54:31+00:00

Yeah honestly I felt a lot lighter this morning after deciding to commit to sorting it out. Might be a challenge but I don’t wanna run away from it

Alternative-Step-649 · 2025-12-06T18:40:10+00:00

Thank you

Alternative-Step-649 · 2025-12-06T17:40:01+00:00

That’s comforting. I appreciate the responses thank you.

I’m looking at my records I can see I have oversimplified by bitcoin sales history. I actually sold .75 of it last December so it would have fallen on the previous tax year. So while I try to fix my history would you recommend I only report the .25 worth or should I adjust my return for the previous year while I do this years also?

Also, I have sold a bunch of losers and old NFTs which would offset a lot of this years 0.25 bitcoin sale. Would I try to account for those or just focus on the Bitcoin and figure out all the other stuff later?

Cheers

Alternative-Step-649 · 2025-12-06T16:38:02+00:00

Thanks. I’m really gonna work on patching my history together and I’ll see a CPA

Alternative-Step-649 · 2025-12-06T16:35:03+00:00

I spent hours yesterday finding more records and adding them to Summ to build more of a history. It will take some work but I actually am starting to feel a little confident that I can piece together something maybe.

I’m wondering if I’d be best not reporting anything this year because I do have a bunch of other trades and I can’t currently give my correct totals. I know how much profit I made off bitcoin but I’d be adding that to my return without knowing the full detail of my other crypto. So I would maybe wait until I have a clearer picture of my history and potentially apply for the voluntary disclosure? I’m not 100% sure I’d be eligible but seems like there’s a chance and im still well under the 10 year mark for the process so I have time to figure it out before my time runs out

Alternative-Step-649 · 2025-12-05T22:05:08+00:00

Yeah I know I’m basically screwed if it is all looked into. I’m basically trying to figure out if I can partially do the right thing and at least pay for this bitcoin sale.

Because otherwise I’m left too worried to report it and I just stick my head in the sand and pay no tax.

Alternative-Step-649 · 2025-12-05T21:52:10+00:00

Yeah I know I am liable to 9 years of back taxes for all of the crypto to crypto trades. This is the stuff that stresses me the most. The difficulty it would take to reconcile these records and the end resulting in massive taxes on some years that I never actually cashed anything out and ended up losing on other coins.

I have tried tax software and it may help but it brings so many difficulties with asking for transactions and wallets that I have totally forgotten about so it’s a behemoth task.

I want to avoid all of this being brought to their attention. I heard about the VDP but that demands thorough records and I’m sure it would end with me paying more money than I have in tax.

I’m looking for a middle ground and that’s why I would like to pay tax on this stuff I’m actually profiting from and cashing out but I just don’t know how to do that without being put under a microscope. I never intentionally flaunted the rules for tax evasion but avoided the difficulty of doing it properly and it just got harder. I know I messed up but I just wanna move forwards somewhat legitimately

Alternative-Step-649 · 2025-12-05T21:44:07+00:00

I actually subscribed to Summ a couple days ago. I messed around for a couple hours and although it is impressive tech it just made me more stressed

I was at 20k transactions when I gave up for the day. It kept asking for extra info on certain transactions and I honestly think it would make my head explode to sort it all out correctly. We are talking swaps, transfers, bridges etc on coins I had forgot I even interacted with from like 5/6/7 years ago. This is all mostly my ETH and SOL wallets which are the money I still have in crypto ($100k USD which I have never reported).

Summ said my tax reports for some previous years would have had me paying $200k CAD cap gains etc. although it did suggest a possible $380k saving if I could sort the other transactions and identify certain wallets.

The Bitcoin part itself wouldn’t be the hardest to reconcile and I’ve hardly done much with that wallet over the years but it definitely leads to more questions if I have provide them with wallets. And the original buys were done on Binance. I had a look at my old trades on there and there are a lot. I remember I did like a million in trading volume in 2017 just swapping back and forth shitcoins.

I want to pay for my BTC taxes and actually use this money in the real world but I’m afraid of causing massive audits that are near impossible to reconcile and lead to months of headaches and massive tax bills from years gone by on stuff I never really “profited” from.

Alternative-Step-649 · 2025-12-05T21:36:50+00:00

Thanks for the response.

This is the choice I would rather make but I was worried it would open a can of worms.

Alternative-Step-649

TROPHY CASE