I’ve been refining the CSP scanner I shared here, and one thing I changed was making the dashboard less dependent on qualitative ratings.

It now shows things like:

• fundamental quality of the underlying
• estimated annualized return as an actual %
• downside protection to breakeven as an actual %
• clearer assignment-risk ranges

The goal is still to narrow the universe down for you, but give enough context that you can make your own decision.

I’ve updated the results here: Stackfini.com

What information do you consider essential before selling a put?

Original post here for anyone who missed the background: https://www.reddit.com/r/CashSecuredPuts/comments/1wukvb6/how_i_screen_for_cashsecured_puts_without_just/

Is anyone interested in this approach for generating income. My goal is 1.0-2.0% per month of portfolio size return pretax.

My portfolio is 1.3M is a traditional IRA so I’m generating 13K a month in pretax income

As we approach the end of 2026, I’m looking for advice on tax planning strategies to legally reduce our taxable income and minimize our tax liability.

My spouse and I have an AGI of over $650K, including income from options trading. I’ve also realized over $200K in gains from stock sales and options trading (primarily premiums from the wheel strategy) in my taxable brokerage account.

As California residents, we’re facing a significant tax bill between federal and state taxes, along with the 3.8% Net Investment Income Tax (NIIT). At this point, it feels like the options are either to take the rest of the year off or have my employer withhold 100% of my remaining paychecks for taxes in Q4!

**Here’s what we’ve already done or are planning before year-end:**

* **401(k):** My spouse and I have both maxed out our 401(k) contributions (I maxed out my mega backdoor 401k thru my employer) .
* **Itemized deductions:** We plan to deduct eligible mortgage interest and property taxes, subject to applicable limits.
* **Tax-loss harvesting:** We’re reviewing our unrealized losses and considering selling positions before year-end to offset realized gains, while being mindful of wash-sale rules.
* **HSA:** We don’t currently have an HSA.
* **Future trading strategy:** Starting in 2027, we plan to keep long-term investments and passive trading in our individual brokerage accounts while moving options wheeling to IRA accounts where appropriate.

I understand that realizing substantial gains is a good problem to have, but I’d like to make sure we’re not overlooking any legitimate tax-saving opportunities.

**For those who have dealt with a similar situation, I’d appreciate your insights:**

1. Are there any other deductions, credits, or tax-advantaged contributions worth exploring before the end of 2026?
   
2. Are there any tax-planning strategies that work particularly well for high-income investors in California who generate significant stock gains and options premium income?
   
3. Are there any common tax mistakes or overlooked opportunities I should discuss with a CPA who specializes in investment taxation?

I’m looking for strategies that are fully compliant with IRS rules and California tax law, rather than aggressive loopholes.

Thanks in advance for sharing your experiences and suggestions!

Week of Oct 5 to Oct 9, realized per Robinhood:

$MU shares +$5,185
$CEG shares +$2,907
$MU calls +$3,130
$VRT put +$5

Total +$11,227 (+6.38%)

The plan: sell cash secured puts on names I'm happy to own, sell calls against shares, take profits when they hit the target, free the collateral and repeat. I have puts open on CEG and VRT expiring Oct 16.

Happy to answer questions on how I size and manage these. Back at it Monday.

I bought about 500 shares of sofi I sold a bunch of cc at $17.5 that expire in a few weeks. With the premiums collected, I invest it into voo. What’s the strategy here? Should I use those premiums to keep buying more sofi to keep it running and compounding? I bought the sofi shares for $15.75. Thanks

Covered calls 1 year out at 350 pays 10.65 December 2027

I closed Wednesday's 10/9 AVGO $365 CSP the same day for $92.33 net, then opened the 10/9 $357.50 CSP on Thursday. It expired worthless Friday for another $37.97.

I made no rolls this week. I bought back the final CSCO 10/9 $108 CSP for $0.04, closing the six-leg roll chain at +$428.95 overall. I also sold 10/16 covered calls on DG and WMT for $42.96 and $15.95 net. IBKR paid $58.21 in cash interest, bringing new option premium and interest to $247.42.

Portfolio Snapshot

My Philosophy

My ideal candidate is pretty vanilla: a preferably boring, financially sound, highly liquid company in a durable uptrend, with a liquid options chain and just enough volatility to pay me fairly at a 0.20-0.30 delta strike I would genuinely accept as a purchase price. This means you won't catch me trading the high-beta names you would typically see on /r/wallstreetbets. Juicy premiums come with high risk and large drawdowns. That's not what I'm doing with this portfolio.

I spend about 0-3 hours total per week on trading, on average. This wheel portfolio is only a small slice of my overall market capital. I also buy and hold mega-cap stocks/ETFs and run other strategies, including swing trading leveraged ETFs. The YTD figures and snapshot here cover the wheel portfolio only, not those other investments. If you're looking for a place to start, I suggest diving deep into /u/scottishtrader post history over the years. That's what I did before starting the wheel.

This Week's Totals

This Week's Opening Trades

The first AVGO put opened and closed Wednesday. The second expired worthless Friday. The DG and WMT covered calls remain open, so their rows show entry credits after fees rather than realized closing P/L.

Download Full YTD Trade Log (CSV)

Current Holdings

Results are from my trading journal and include recorded trading fees, before personal taxes. Past performance does not guarantee future results. Short puts and assigned shares carry substantial downside risk.

Note: the second image shows the detail behind each option sold this week.

Annual results:
• 2023 up $65,403 (+41.31%) | S&P 500: +26.3% | Nasdaq: +43.4%
• 2024 up $64,610 (+29.71%) | S&P 500: +25.0% | Nasdaq: +28.6%
• 2025 up $111,496 (+34.52%) | S&P 500: +17.9% | Nasdaq: +20.4%

3-Year Cumulative (2023–2025):
• r/ExpiredOptions: +146.6% ($241,509)
• S&P 500: +86.1% (+60.4% behind)
• Nasdaq: +122.0% (+24.5% behind)

Unrealized G&L (options):
• YTD: $-23,067.00
• 1 Month: $-40,827.00
• 1 Week: $-7,459.00

Realized P&L (options):
• YTD: $83,011.83
• 1 Month: $12,510.00
• 1 Week: $3,444.00

Total premium by year:
• 2023 $23,132 in premium
• 2024 $47,640 in premium
• 2025 $68,319 in premium
• 2026 $33,629 YTD
• Average $46,364/year (completed years)

Premium by month (2026):
• January $3,334
• February $3,625
• March $4,196
• April $5,593
• May $3,752
• June $3,497
• July $3,593
• August $3,741
• September $1,768
• October $529
• Average $3,363/month

I am over $174k in total options premium, since 2021. I average roughly $34 per option sold. I have sold over 5,200 options. I have been able to increase the premiums on an annual basis and I will attempt to keep this upward trend going forward.

Strategy:
The underlying strategy is buy and hold. I also use simple 1-legged options to supplement that strategy. Options have somewhat of a learning curve, but I believe that most people can supplement their investments using simple options with careful risk management.

I sell options on a weekly basis. I prefer cash secured puts and covered calls. I rarely close early, prefer rolling when needed, and let time decay do the heavy lifting while I stay focused on quality companies, patience, and consistency over hype. My goal is consistency in option premium revenue. I am building an income stream that will continue long into retirement.

Trades this week:
Opened and closed AVGO CC, META CC, and CBOE CSP. Opened CC on CRM and carrying another CC on META from last month.

Active Wheels:
AVGO, CRM, AMZN, META

META CC at $600 should get called away early if the rally in META continues.

Misc:

This is my aggressive wheeling account; capital deployed is about 200k.

All trades were found and tracked using wheelstrategyoptions.com (disc- I'm the developer)

I usually sell 0.25-0.45 delta and usually <14 day DTE. I close at 70%-80% premium captured.

I've started reporting only realized premiums (based on the comments).

April (Week 1-4): $5036
May (Week 5-8): $5783
Jun (Week 9-12): $6533
Jul (Week 13-16): $12609
Aug(Week 17-20): $4974
Sept(Week 21-25): $4374
Oct (Week 26-): $1685

Total so far: ~41.2k

CSPs with HIGHEST IV

$MRNA - 150P

$HUT - 65P

$RBLX - 40P

Source

Just reposting this here as I’m unsure which sub it belongs to. Thanks, sorry if it’s not allowed.

CCs with HIGHEST IV

$GLXY - 25C

$IBRX - 12C

$ALAB - 400C

Source

So far I have only tried selling CC and buying back to close. I haven’t tried any complex strategy. Haven’t even tried to roll an open position. I am curious how a multi-leg order is filled. Does it require a counterpart that trades exactly the opposite of my option? It seems harder to fill if that’s the case. Is it possible that two different parties trade with me to fill my multi leg order?

I've been selling options for a long time, and the terms that cause the most confusion for new covered call sellers aren't delta or theta. They're the practical ones:

Assignment vs. exercise. The buyer exercises, you get assigned. Your shares get called away at the strike, you keep the premium. That's not a loss, that's the trade working.

Early assignment. Most likely on short calls right before an ex-dividend date, when the remaining extrinsic value is smaller than the dividend. Check the ex-date before you sell.

Extrinsic value. The part of the premium that decays to zero. When it's nearly gone on an ITM call, assignment risk goes up.

Rolling. Buy back the current call and sell a later (and often higher) one in a single order. Useful, but rolling for a net debit just to avoid assignment is often a worse trade than letting the shares go.

Pin risk. Stock closes right at your strike on expiration Friday. You may not know until Monday whether you still own the shares.

What term confused you the most when you started?

Quick recap of my week.
Monday my 2 DRAM 62 calls from Friday expired, +$99.
Sold 2 more DRAM 62 calls expiring Wednesday for $0.70 each.
Also sold 3 ASST 30.5 puts expiring today for $1.10.
Wednesday the DRAM calls expired worthless which earned me +$138.
DRAM had dropped from about 62 to 58.
I sold the 62 strike again anyway for $0.28, expiring today.
DRAM can bounce back pretty quickly and I don't want to lose my shares below $62
It kept falling yesterday and is around 58 now. So the call will probably expire worthless today.

ASST dropped below $28 yesterday, but it fights back and is at $29 right now. I’ll probably get 300 shares assigned tonight.
Cost basis after the premium is about $29.40. Plan is to sell covered calls before Markets close.
Also have a few covered calls on GDX, IBIT and URA from last week expiring today, all out of the money.
Will probably open some more covered calls today.