Rolled Out and Up The Cigna Group Covered Call Position

The Covered Calls Advisor Portfolio has a Covered Call position in The Cigna Group (ticker CI) that has a June 16th, 2023 (i.e. tomorrow) expiration date at the $255.00 strike price.  Today, Cigna stock was trading well above the strike price at $272.55, so with only $.05 time value remaining in the Calls, I decided to roll-out-and-up one week to the June 23rd expiration at the $265.00 strike price.  

This Covered Call position was originally established on March 1st, 2023 when the stock was purchased at $289.40 per share.  It immediately began a price decline which has been accompanied by a net unrealized loss for this position. The stock price declined to a low of $240.50 (fully 16.9% below the stock purchase price); but I remained bullish on Cigna and have continued to rollout the position at each expiration date in an effort to attempt to repair this losing position back toward profitability.    

As detailed below, a potential return-on-investment result is -1.0% absolute return (equivalent to -3.2% annualized return-on-investment for the 115 days holding period) if Cigna's price remains in-the-money (i.e. above the $265.00 strike price) on the June 23rd, 2023 options expiration date.  

The Cigna Corporation (CI) -- Covered Call Position Continued by Rolling-Out-and-Up
The original buy/write transaction was as follows:
3/1/2023 Bought 100 Cigna Corp. shares @ $289.40
3/1/2023 Sold 1 Cigna 3/17/2023 $280.00 Call option @ $11.70
3/7/2023 Quarterly ex-dividend of $1.23 per share
3/17/2023 One Cigna Call option expired out-of-the-money and 100 shares remain in the Covered Calls Advisor Portfolio
3/21/2023 Continued Cigna Covered Call position by selling one March 31st, 2023 $27.50 Call option @ $4.10 per share.  The stock price was $276.68 when this transaction was made.
3/31/2023 One Cigna Call option expired out-of-the-money and 100 shares remain in the Covered Calls Advisor Portfolio
4/3/2023 Continued Cigna Covered Call position by selling one April 21st, 2023 $270.00 Call option @ $2.50 per share.  The stock price was $262.30 when this transaction was made and the Delta for this Call option was 29.9.
4/24/2023 Continued Cigna Covered Call position by selling one May 12th, 2023 $265.00 Call option @ $3.52 per share.  The stock price was $256.47 when this transaction was made and the Delta for this Call option was 43.2.
5/12/2023 Continued Cigna Covered Call position by executing a net credit Call spread at $3.00 per share by buying-to-close one May 12th, 2023 $265.00 Call and simultaneously selling-to-open one May 26th, 2023 $260.00 Call option.  The Implied Volatility of the new Call was 21.8 and the Delta was 38.8 when this transaction was made.
5/26/2023 One Cigna Call option expired out-of-the-money and 100 shares remain in the Covered Calls Advisor Portfolio
6/1/2023 Continued Cigna Covered Call position by selling one June 16th, 2023 $255.00 Call option @ $3.70 per share.
6/6/2023 Quarterly ex-dividend of $1.23 per share.
6/15/2023 Continued this Covered Call position by rolling-up-and-out with a net debit Call spread @ $9.30 per share.  I bought-to-close the 6/16/2023 $255.00 Call at $17.50 when its remaining time value was only $.05 since the stock price was then at $272.55 per share; and simultaneously sold-to-open the 6/23/2023 $265.00 Call at $8.20 per share.  A potential overall performance result for this ongoing Cigna Covered Call position is as follows:

Covered Call Cost Basis: $27,770.67
= ($289.40 - $11.70) * 100 shares + $.67 commissions

Net Profit Components:
(a) Options Income: +$1,917.31
= ($11.70 + $4.10 + $2.50 + $3.52 -$.06 +$3.06 +$3.70 -$17.50 +$8.20) * 100 shares - $4.69 commissions
(b) Dividend Income: +$246.00
= ($1.23 dividend per share x 100 shares) x 2 quarterly dividends
(c) Capital Appreciation (If Cigna shares assigned at $265.00 strike price at the 6/23/2023 options expiration): -$2,440.00
+($265.00 - $289.40) * 100 shares

Total Net Profit (If Cigna shares assigned at $265.00 strike price at the June 23rd, 2023 expiration): -$276.69

= (+$1,917.31 options income + $246.00 dividend income - $2,440.00 capital appreciation)

Absolute Return-on-Investment (If Cigna shares assigned at $265.00 strike price on the 6/23/2023  expiration): -1.0%

= -$276.69/$27,770.67

Annualized Return-on-Investment (If Cigna stock assigned at $265.00 at the 6/23/2023 options expiration date): -3.2%

= (-$276.69/$27,770.67) * (365/115 days)