I’ve been learning how to trade stock options. Specifically, I am learning to trade cash secured puts and covered calls. Basically, it is the Wheel strategy with some slight modifications.
I am getting very serious about trading them and decided to document my learning journey in one centralized location.
This online journal and knowledge repository is that location.
At 1 PM MST. I checked my trades for what I should be doing with the help of AI (which I always double check).
Looking at your option positions for Friday, July 25, 2025 (EXPIRATION DAY), here’s the analysis:
EXPIRATION DAY POSITIONS – SPECIAL FRIDAY RULES APPLY
CHWY $38 PUT (Expires TODAY)
- Current Price: $36.265
- Strike: $38
- Status: ITM by 4.57% ($1.735 ITM)
- ACTION: ROLL IMMEDIATELY for shortest time with good premium
- Target: Roll to next week (August 1) or 2 weeks out
- Premium Target:
- 1 week: $38 × 0.01 × 1 = $0.38/share ($38/contract)
- 2 weeks: $38 × 0.01 × 2 = $0.76/share ($76/contract)
The premium for rolling it a single week to August 1, 2025 was a debit when I looked at it (which I did not expect to see). However, when I looked at it to write this post about 35 minutes later, it does show a small credit for a week out.
CHWY Put Roll Transaction
Closing Position:
- Jul 25, 2025 $38.00 Put
- Buy to close: 1 contract at $1.56
Opening Position:
- Aug 01, 2025 $38.00 Put
- Sell to open: 1 contract at $1.62
Transaction Summary:
- Net Credit: $0.06
- Midpoint: $0.16
- Net Ask: $0.26
- Evaluation Price: $0.25
Rolling out one week from July 25 to August 1, maintaining the $38 strike price. Collected a small net credit of $6 per contract after closing the expiring position.
I ended up doing this (2 weeks out) by letting my order sit for about 15 minutes:
CHWY Put Roll Transaction
Closing Position:
- Jul 25, 2025 $38.00 Put
- Buy to close: 9 contracts at $1.63
- Total cost: $1,467
Opening Position:
- Aug 08, 2025 $38.00 Put
- Sell to open: 9 contracts at $1.97
- Total credit: $1,773
Transaction Summary:
- Net Credit: $0.34 per contract
- Total Net Credit: $306 (9 contracts)
- Roll Duration: 2 weeks (July 25 to August 8)
- Strike Price Maintained: $38.00
- Return on Risk (ROR): 0.89% for 2 weeks (0.445% per week)
- Annualized ROR: 23.2%
Successfully rolled the expiring CHWY position out two weeks, collecting a net credit of $34 per contract. While this is below the 1% weekly target of $76 per contract for a 2-week roll, it was necessary to avoid assignment on expiration day.
MU $114 PUT (Expires TODAY)
- Current Price: $110.92
- Strike: $114
- Status: ITM by 2.70% ($3.08 ITM)
- ACTION: ROLL IMMEDIATELY for shortest time with good premium
- Target: Roll to next week or 2 weeks out
- Premium Target:
- 1 week: $114 × 0.01 × 1 = $1.14/share ($114/contract)
- 2 weeks: $114 × 0.01 × 2 = $2.28/share ($228/contract)
I rolled these out for a little under 1%.
MU Put Roll Transaction
Closing Position:
- Jul 25, 2025 $114.00 Put
- Buy to close: 3 contracts at $3.12
- Total cost: $936
Opening Position:
- Aug 01, 2025 $114.00 Put
- Sell to open: 3 contracts at $4.05
- Total credit: $1,215
Transaction Summary:
- Net Credit: $0.93 per contract
- Total Net Credit: $279 (3 contracts)
- Roll Duration: 1 week (July 25 to August 1)
- Strike Price Maintained: $114.00
- Return on Risk (ROR): 0.82% for 1 week
- Annualized ROR: 42.6%
Successfully rolled the expiring MU position out one week, collecting a net credit of $93 per contract. This falls slightly short of the 1% weekly target of $114 per contract, but was necessary to avoid assignment on expiration day.
OSCR $14 PUT (Expires TODAY)
- Current Price: $14.325
- Strike: $14
- Status: OTM by 2.32%
- ACTION: Let expire worthless (clearly OTM on expiration day)
RUN $9.50 PUT (Expires TODAY)
- Current Price: $10.555
- Strike: $9.50
- Status: OTM by 11.11%
- ACTION: Let expire worthless (clearly OTM on expiration day)
ZIM $15.50 PUT (Expires TODAY)
- Current Price: $16.605
- Strike: $15.50
- Status: OTM by 7.13%
- ACTION: Let expire worthless (clearly OTM on expiration day)
NOT EXPIRATION WEEK POSITIONS
KHC $26 CALL (Expires August 29, 2025)
- Days to Expiration: 35 days
- Current Price: $28.66
- Strike: $26
- Status: ITM by 10.23% ($2.66 ITM)
- ACTION: ROLL OUT 6 WEEKS FROM TODAY
- Target Date: September 5, 2025
- Premium Target: $26 × 0.01 × 6 = $1.56/share ($156/contract)
UNH $295 CALL (Expires August 1, 2025)
- Days to Expiration: 7 days
- Current Price: $281.08
- Strike: $295
- Status: OTM by 4.71%
- ACTION: OTM – DO NOTHING (entering expiration week)
SUMMARY
IMMEDIATE ACTIONS REQUIRED (Expiration Day):
- ROLL CHWY $38 PUT – ITM by 4.57%, roll to shortest timeframe with $38+ premium (1 week) or $76+ (2 weeks)
- ROLL MU $114 PUT – ITM by 2.70%, roll to shortest timeframe with $114+ premium (1 week) or $228+ (2 weeks)
OTHER ACTIONS:
NO ACTION REQUIRED:
- OSCR $14 PUT – Let expire worthless (OTM)
- RUN $9.50 PUT – Let expire worthless (OTM)
- ZIM $15.50 PUT – Let expire worthless (OTM)
- UNH $295 CALL – OTM, entering expiration week next week
Remember: For the Friday rolls (CHWY and MU), prioritize getting them rolled today even if it means accepting slightly less than the 1% weekly target, as avoiding assignment takes precedence on expiration day.