Been screwing around with Claude Max and an Obsidian vault trying to get more sophisticated with rolling covered calls and investing in general. I fed it my entire transaction history for calls (1,500+ rolls) and my current positions, then I loaded it up with a bunch of pdfs of books/academic research papers about options trading and investing that I was able to find on Google Scholar. The sources RE: options were really deep stuff about greeks and all kinds of other interesting things to consider, I understood some of it from my FINC421 days at Mays. I think.
I've got it dialed in now where I email myself a csv with all my positions from the office with the subject "cc run" during market open hours. Claude (living on my Mac Mini in my home office) sweeps my inbox looking for "cc run" emails once per minute when the market is open, so it grabs the email almost immediately It ingests the positions csv, ingests the full current option chain <90 DTE for all the underlyings from IBKR (most of the time, it wasn't able to connect today - that's why it says "check chain" instead of giving me the date and strike price to look for so I'll just figure it out manually for today), and gives me all the pertinent info and recommended action.
It thinks I was rolling too early, it usually wants me to go slightly longer than ~40 DTE for the roll out and hold it for 20+ days to farm more theta. Here is the report from this morning, figured I would share since I've been pretty transparent about this strategy up to this point.
I really need to play defense on INTC to avoid getting assigned, so I'm probably going to go ahead and roll all the WATCH recommendations in that account to free up some cash, then pay to get INTC up and out of danger. My cost basis is like $43 on those shares so I basically bought and opened the positions right before it went bonkers, same thing that happened to me with GLD and especially SLV recently. Managed to hang on to all the shares so far though and the calls are throwing off a ton of premium, so good problem to have.
TLDR - I made a robot that knows more about options trading than me, it emails me what to do with my covered calls:
# CC ROLL REPORT - 2026-05-05
**38 positions** | ROLL: 3 HOLD: 3 WATCH: 32
> **VIX 18.3 - LOW WARNING: history shows lower avg returns below VIX > 20**
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## Health Savings Account `249xxxxxxxx`
| Ticker | Underlying | Exp | Strike | Cts | ITM / OTM | Intrinsic | Extrinsic | Action | Roll Exp | Roll Strike | Net/share | Flags |
|--------|-----------|-----|--------|-----|-----------|-----------|-----------|--------|----------|-------------|-----------|-------|
| IBIT | $46.16 | 06-05 | $48 | 2 | OTM $1.84 | $0.00 | $1.18 | WATCH | - | - | - | - |
| MSTR | $188.29 | 06-05 | $175 | 2 | ITM $13.29 | $13.29 | $6.41 | WATCH | - | - | - | beta =3.6
| NVDA | $199.05 | 06-05 | $195 | 1 | ITM $4.05 | $4.05 | $8.09 | WATCH | - | - | - | beta=2.2 | 52w=8% |
---
## Brokerage `Z31xxxxxxx`
| Ticker | Underlying | Exp | Strike | Cts | ITM / OTM | Intrinsic | Extrinsic | Action | Roll Exp | Roll Strike | Net/share | Flags |
|--------|-----------|-----|--------|-----|-----------|-----------|-----------|--------|----------|-------------|-----------|-------|
| GLD | $420.55 | 06-18 | $380 | 1 | ITM $40.55 | $40.55 | $0.00 | WATCH | - | - | - | - |
| GLD | $420.55 | 06-18 | $385 | 1 | ITM $35.55 | $35.55 | $0.75 | WATCH | - | - | - | - |
| IBIT | $46.16 | 06-05 | $48 | 2 | OTM $1.84 | $0.00 | $1.18 | WATCH | - | - | - | - |
| IWM | $280.64 | 06-18 | $245 | 1 | ITM $35.64 | $35.64 | $0.00 | WATCH | - | - | - | - |
| MSTR | $188.29 | 06-05 | $170 | 2 | ITM $18.29 | $18.29 | $4.24 | WATCH | - | - | - | beta=3.6 |
| NVDA | $199.05 | 06-05 | $195 | 1 | ITM | $4.05 | $4.05 | $8.09 | WATCH | - | - | - | beta=2.2 52w=8% |
| QQQ | $679.25 | 06-18 | $625 | 1 | ITM $54.25 | $54.25 | $1.85 | WATCH | - | - | - | - |
| SPY | $722.31 | 06-05 | $696 | 1 | ITM $26.31 | $26.31 | $4.01 | WATCH | - | - | - | - |
---
## ROTH IRA `245xxxxxxxxx`
| Ticker | Underlying | Exp | Strike | Cts | ITM / OTM | Intrinsic | Extrinsic | Action | Roll Exp | Roll Strike | Net/share | Flags |
|--------|-----------|-----|--------|-----|-----------|-----------|-----------|--------|----------|-------------|-----------|-------|
| SPY | $722.31 | 06-05 | $700 | 1 | ITM $22.31 | $22.31 | $4.96 | WATCH | - | - | - | - |
---
## Rollover IRA `244xxxxxxxx`
| Ticker | Underlying | Exp | Strike | Cts | ITM / OTM | Intrinsic | Extrinsic | Action | Roll Exp | Roll Strike | Net/share | Flags |
|--------|-----------|-----|--------|-----|-----------|-----------|-----------|--------|----------|-------------|-----------|-------|
| BRKB | $467.38 | 05-29 | $510 | 1 | OTM $42.62 | $0.00 | $0.68 | **ROLL** | check chain | - | - | beta=0.6 |
| INTC | $105.84 | 05-29 | $54 | 4 | ITM $51.84 | $51.84 | $0.00 | **ROLL** | check chain | - | - | beta=2.2 52w=1% | | AMD | $350.60 | 06-18 | $260 | 1 | ITM $90.60 | $90.60 | $0.00 | WATCH | - | - | - | beta=2.4 52w=3% |
| GLD | $420.55 | 06-05 | $345 | 2 | ITM $75.55 | $75.55 | $2.30 | WATCH | - | - | - | - | |
| GOOGL | $389.38 | 06-18 | $305 | 1 | ITM $84.38 | $84.38 | $0.00 | WATCH | -| - | - | beta=1.3 52w=0% |
| HOOD | $77.65 | 06-05 | $103 | 1 | OTM $25.35 | $0.00 | $0.36 | WATCH | - | - | - | beta=2.3 |
| IBIT | $46.16 | 06-05 || $48 | 1 | OTM $1.84 | $0.00 | $1.18 | WATCH | - | - | - | - |
| MSFT | $412.16 | 06-18 | $430 | 1 | OTM $17.84 | $0.00 | $9.51 | WATCH | - | - | - | beta=1.1 |
| MSTR | $188.29 | 06-05 | $177.5 | 1 | ITM $10.79 | $10.79 | $7.68 | WATCH | - | - | - | beta=3.6 |
| MSTR | $188.29 | 06-05 | $250 | 1 | OTM $61.71 | $0.00 | $2.57 | WATCH | - | - | - | beta=3.6 |
| NVDA | $199.05 | 06-18 | $195 | 4 | ITM $4.05 | $4.05 | $9.66 | WATCH | - | - | - | beta=2.2 52w=8% |
| PLTR | $139.38 | 06-05 | $182.5 | 1 | OTM | $43.12 | $0.00 | $1.86 | WATCH | - | - | - | beta=1.5 |
| QQQ | $679.25 | 06-18 | $625 | 2 | ITM $54.25 | $54.25 | $1.85 | WATCH | - | - | - | -|
| SLV | $66.50 | 06-05 | $45 | 5 | ITM $21.50 | $21.50 | $1.92 | WATCH | - | - | - | - |
| SMH | $518.70 | 06-18 | $400 | 1 | ITM $118.70 | $118.70 | $0.00 | WATCH | - | - | - | - |
| SPY | $722.31 | 06-05 | $692 | 2 | ITM $30.31 | $30.31 | $3.20 | WATCH | - | - | - | - |
| XLF | $51.53 | 06-05 | $54 | 10 | OTM $2.47 | $0.00 | $0.27 | WATCH | - | - | - | - |
| AAPL | $279.40 | 06-05 | $280 | 1 | OTM $0.60 | $0.00 | $6.40 | HOLD | - | - | - | beta=1.1 52w=3% |
| AMZN | $276.91 | 06-05 | $240 | 2 | ITM $36.91 | $36.91 | $0.00 | HOLD | - | - | - | beta=1.5| 52w=0% |
| TSLA | $399.66 | 06-18 | $445 | 3 | OTM $45.34 | $0.00 || $7.64 | HOLD | - | - | - | beta=1.8 |
---
## Rollover IRA `263xxxxxxxx`
| Ticker | Underlying | Exp | Strike | Cts | ITM / OTM | Intrinsic | Extrinsic | Action | Roll Exp | Roll Strike | Net/share | Flags |
|--------|-----------|-----|--------|-----|-----------|-----------|-----------|--------|----------|-------------|-----------|-------|
| AMZN | $276.91 | 06-18 | $235 | 1 | ITM $41.91 | $41.91 | $0.00 | WATCH | - | - | - | beta=1.5 52w=0% |
| QQQ | $679.25 | 06-18 | $615 | 1 | ITM $64.25 | $64.25 | $1.30 | WATCH | - | - | - | - |
| SMH | $518.70 | 06-18 | $445 | 1 | ITM $73.70 | $73.70 | $0.00 | WATCH | - | - | - | -|
| XLE | $59.37 | 06-18 | $65 | 1 | OTM $5.63 | $0.00 | $0.62 | WATCH | - | - | - | - |
---
## ROTH IRA `268xxxxxxxxx`
| Ticker | Underlying | Exp | Strike | Cts | ITM / OTM | Intrinsic | Extrinsic | Action | Roll Exp | Roll Strike | Net/share | Flags |
|--------|-----------|-----|--------|-----|-----------|-----------|-----------|--------|----------|-------------|-----------|-------|
| IBIT | $46.16 | 05-29 | $53 | 3 | OTM $6.84 | $0.00 | $0.18 | **ROLL** | check chain | - | - | - |
| QQQ | $679.25 | 06-18 | $615 | 1 | ITM | $64.25 | $64.25 | $1.30 | WATCH | - | - | - | - |