LEAPS Extend · 2026-10-30 · All fortresses

MSTR · RetireInc

+4 Jan 21 '28 125C-4 Jan 21 '28 185P+4 Dec 18 '26 55P448 days leftCSV ND 12.00entry $163 -18.1%CC-SS $156.34 (+17% vs spot)BE-SS $161.00 (+21% vs spot)
Spot
$133.54
CBOE 2026-10-30 00:14:49
When to roll⏸ WAIT
Wait until 23 Oct 2027
  • 448 days left. Nothing forces a roll before 23 Oct 2027 (90 days before expiry): waiting keeps today's structure and costs nothing extra in spread.
  • The new expiry is still wide (worst leg spread 12% of mid, open interest as low as 69): work the order at mid, never natural.
Re-run then, or sooner after a 15%+ drop (a lower price makes extending cheaper and more urgent).
Is the time worth buying! EXTEND FOR RECOVERY
Engine stalled: extending is a bet on recovery
  • Since 2026-05-31 it has banked $435, $48/mo with the open call chain marked to today's buyback; the last 90 days $153/mo against a $947/mo floor and a $1,893/mo design.
  • Safe calls (at or above the $156 CC-SS) only pay a normal premium from about $137 (+3% from here).
  • FIGHT engine (~0.30-delta calls below the CC-SS, where an assignment locks a loss): about $1,405/mo at MSTR's realized keep of 81% (22 closed calls).
  • The record does not show the FIGHT engine running ($153/mo earned vs $1,405/mo modelled): only safe-call income is credited.
  • Extending to Jun 16 '28 buys 5 months. Expected income to expiry with FIGHT: $22,160 if you keep, $31,428 after the roll; safe calls alone: $16,854 vs $23,896. Odds safe calls restart: 73% vs 68%.
  • At the record's pace the extra 5 months are worth about $738.
  • Even after the roll the odds are only 68%: the extension is a bet on recovery, with little income in the meantime.
  • Coverage Insights: write closer: today the sweet spot 185C offers $439/mo, 2.9x what it earns.
  • Earnings 2026-10-30 (1 days): sell no new income into it.

Today, if you keep it

Value now (mid)
-$5,811
Unrealized vs CSV ND
-$10,611
Max loss from here
$46,189
Margin it holds (model)
$34,615
a close frees it; $34,615 on all MSTR here
CC-SS
$156.34
safe call from $137
Net delta
+486 sh
notional $53,416
Theta
~$0/day
net of the three legs
Short put time value
$16.04
assignment LOW
If you close it today
Whole-life P/L
-$10,508
legs + call income, all in
Legs vs entry
-$10,611
close LC / SP / HP at mid vs CSV ND
Call income banked
+$435
since entry, incl. the open chain
Cash to close today
-$6,143
legs at mid + call buyback -$332
If you hold to expiry instead
Whole-life P/L at expiry
-$567
expected; -$10,508 if closed today
Chance of break-even
35%
whole-life P/L at or above zero
Max loss left
$46,189
19% of the $56,800 at entry already taken
Worst case if held
-$56,697
legs at their worst, no call income
No roll and no close: calls written every cycle to Jan 21 '28 (safe calls only). Spot at expiry is spread lognormal at realized vol, zero drift. Holding keeps $34,615 of margin a close would free, counted dollar for dollar: holding trails closing by $24,675.

Recommended roll

BEST: cash + margin · also BEST WITH INCOME, MOST CASH
-$7,761
cash at mid today (natural -$11,671)
FULLJun 16 '28+5 months
SELL 4 Jan 21 '28 125C (close)
BUY 4 Jan 21 '28 185P (close)
SELL 4 Dec 18 '26 55P (close)
BUY 4 Jun 16 '28 110C (open)
SELL 4 Jun 16 '28 185P (open)
BUY 4 Jun 16 '28 75P (open)
Margin change
-$3,682
freed is good; IBKR: IBKR's margin engine answers only in US market hours (21:30-04:00 SGT)
Hedge extension (est.)
none
hedge rolled too
Income over the time bought
$230
actual: $48 a month x 5 months; covers all of the max loss it adds
Restart odds
73% → 68%
safe calls paying before expiry
Max loss from here
$45,950
-$239 vs keep
CC-SS
$158.76
now $156.34
CSV ND after
31.40
at a mid fill

If you're assigned

Income outlook

Income history · since 2026-05-31
Banked since entry
$435
closed calls + open chain premium
Life-to-date pace
$48/mo
open chain marked to today's buyback
Last 90 days
$153/mo
Coverage Insights' window
Best month
$580
Jun 2026
May
$580
Jun
Jul
Aug
Sep
Oct
$240
open
life pace $48/mo
Closed call net per calendar month (first and last months are part months). The hatched bar is the open roll chain: premium collected but not yet closed. Hover a bar for detail.
Last 90 days vs design
$153/mo
BELOW DESIGN
floor $947
design $1,893
$153/mo earned pays the hedge but is under half of the $1,893/mo it is designed to earn
Scanner's best pick today
$439/mo
Banked so far
$435
Whole-life P/L
-$10,503
Time with a call written
99%
Call roll chain
5 rolls down to 150, $0.60/sh
Source: Coverage Insights 2026-10-30
Market now
Call IV (~35d)
68%
CBOE 30-day 68%
Regime
NEUTRAL
RSI 51
Next earnings
2026-10-30
1 days
FIGHT rate (model)
$1,405/mo
~0.30-delta calls x 81% keep
Where safe calls start paying
safe from $137
spot $134
Spot needs +3% before a safe call pays a normal premium.
What the time buys
Expected income to expiry, FIGHT included (model)
Keep Jan 21 '28
$22,160
Roll Jun 16 '28
$31,428
Odds safe calls start paying before expiry
Keep Jan 21 '28
73%
Roll Jun 16 '28
68%
Safe calls alone (never below the CC-SS)
Keep Jan 21 '28
$16,854
Roll Jun 16 '28
$23,896
Months bought
5
Worth at the record's pace
$738
Engine state
STALLED

Roll choices on Jun 16 '28

Cash received is green, paid is red. Margin freed is green, added is red. Extra income is the model's expected income the extra time adds, FIGHT calls included at the realized keep; extra safe income counts calls at or above the CC-SS only.

BEST: cash + margin

Most cash received net of margin added (the 2026-10-22 rule): the recommended roll.
FULLJun 16 '28also BEST WITH INCOMEalso MOST CASH
Cash at mid
-$7,761
Margin change
-$3,682
Strikes
110C / -185P / +75P
Cash at natural
-$11,671
Extra income, FIGHT incl. (model)
+$9,268 (+$1,917/mo)
Extra safe income (model)
+$7,043 (+$1,456/mo)
Restart odds
68% (keep 73%)
Value incl. income
+$5,190
Max loss from here
$45,950 (-$239)
CC-SS
$158.76 (now $156.34)
Net delta
+451 sh (now +486)
CSV ND after
31.40
Worst spread / min OI
12% / 69
Danger point
none to -60% (now none to -60%)
Order legs
SELL 4 Jan 21 '28 125C (close)
BUY 4 Jan 21 '28 185P (close)
SELL 4 Dec 18 '26 55P (close)
BUY 4 Jun 16 '28 110C (open)
SELL 4 Jun 16 '28 185P (open)
BUY 4 Jun 16 '28 75P (open)

LEAST MARGIN

Largest drop (or smallest rise) in maintenance margin.
FULLJun 16 '28
Cash at mid
-$15,781
Margin change
-$4,542
Strikes
90C / -185P / +100P
Cash at natural
-$20,211
Extra income, FIGHT incl. (model)
+$9,251 (+$1,913/mo)
Extra safe income (model)
+$7,000 (+$1,448/mo)
Restart odds
68% (keep 73%)
Value incl. income
-$1,988
Max loss from here
$43,970 (-$2,219)
CC-SS
$158.98 (now $156.34)
Net delta
+445 sh (now +486)
CSV ND after
51.45
Worst spread / min OI
12% / 99
Danger point
none to -60% (now none to -60%)
Order legs
SELL 4 Jan 21 '28 125C (close)
BUY 4 Jan 21 '28 185P (close)
SELL 4 Dec 18 '26 55P (close)
BUY 4 Jun 16 '28 90C (open)
SELL 4 Jun 16 '28 185P (open)
BUY 4 Jun 16 '28 100P (open)

LOWEST MAX LOSS

Smallest worst-case loss from here.
FULLJun 16 '28
Cash at mid
-$21,691
Margin change
-$4,277
Strikes
75C / -185P / +115P
Cash at natural
-$25,771
Extra income, FIGHT incl. (model)
+$9,262 (+$1,915/mo)
Extra safe income (model)
+$7,026 (+$1,453/mo)
Restart odds
68% (keep 73%)
Value incl. income
-$8,152
Max loss from here
$43,880 (-$2,309)
CC-SS
$158.85 (now $156.34)
Net delta
+442 sh (now +486)
CSV ND after
66.23
Worst spread / min OI
9% / 38
Danger point
none to -60% (now none to -60%)
Order legs
SELL 4 Jan 21 '28 125C (close)
BUY 4 Jan 21 '28 185P (close)
SELL 4 Dec 18 '26 55P (close)
BUY 4 Jun 16 '28 75C (open)
SELL 4 Jun 16 '28 185P (open)
BUY 4 Jun 16 '28 115P (open)

INCOME ENGINE

Most expected income to the new expiry, FIGHT included (model).
FULLJun 16 '28
Cash at mid
-$18,271
Margin change
-$3,094
Strikes
75C / -190P / +105P
Cash at natural
-$22,331
Extra income, FIGHT incl. (model)
+$9,334 (+$1,930/mo)
Extra safe income (model)
+$7,203 (+$1,490/mo)
Restart odds
68% (keep 73%)
Value incl. income
-$5,843
Max loss from here
$46,460 (+$271)
CC-SS
$157.90 (now $156.34)
Net delta
+460 sh (now +486)
CSV ND after
57.68
Worst spread / min OI
9% / 38
Danger point
none to -60% (now none to -60%)
Order legs
SELL 4 Jan 21 '28 125C (close)
BUY 4 Jan 21 '28 185P (close)
SELL 4 Dec 18 '26 55P (close)
BUY 4 Jun 16 '28 75C (open)
SELL 4 Jun 16 '28 190P (open)
BUY 4 Jun 16 '28 105P (open)

SAME STRIKES

The held strikes rolled straight out (reference).
LEAPS ONLYJun 16 '28
Cash at mid
-$860
Margin change
-$675
Strikes
125C / -185P / +55P (kept)
Cash at natural
-$4,040
Hedge extension (est.)
-$580
Extra income, FIGHT incl. (model)
+$9,399 (+$1,944/mo)
Extra safe income (model)
+$7,364 (+$1,523/mo)
Restart odds
69% (keep 73%)
Value incl. income
+$8,634
Max loss from here
$47,049 (+$860)
CC-SS
$157.03 (now $156.34)
Net delta
+476 sh (now +486)
CSV ND after
14.15
Worst spread / min OI
9% / 99
Danger point
none to -60% (now none to -60%)
Order legs
SELL 4 Jan 21 '28 125C (close)
BUY 4 Jan 21 '28 185P (close)
BUY 4 Jun 16 '28 125C (open)
SELL 4 Jun 16 '28 185P (open)

Side by side

FamilyExpiryLCSPHPCash midHedge estMargin chgExtra incomeExtra safeRestartValue incl. incomeMax lossCC-SSDelta sh
KEEPheldJan 21 '2812518555-----73%-$46,189$156.34+486
BESTFULLJun 16 '2811018575-$7,761--$3,682+$9,268
+$1,917/mo
+$7,043
+$1,456/mo
68%+$5,190$45,950$158.76+451
BEST WITH INCOMEFULLJun 16 '2811018575-$7,761--$3,682+$9,268
+$1,917/mo
+$7,043
+$1,456/mo
68%+$5,190$45,950$158.76+451
MOST CASHFULLJun 16 '2811018575-$7,761--$3,682+$9,268
+$1,917/mo
+$7,043
+$1,456/mo
68%+$5,190$45,950$158.76+451
LEAST MARGINFULLJun 16 '2890185100-$15,781--$4,542+$9,251
+$1,913/mo
+$7,000
+$1,448/mo
68%-$1,988$43,970$158.98+445
LOWEST MAX LOSSFULLJun 16 '2875185115-$21,691--$4,277+$9,262
+$1,915/mo
+$7,026
+$1,453/mo
68%-$8,152$43,880$158.85+442
INCOME ENGINEFULLJun 16 '2875190105-$18,271--$3,094+$9,334
+$1,930/mo
+$7,203
+$1,490/mo
68%-$5,843$46,460$157.90+460
SAME STRIKESLEAPS ONLYJun 16 '2812518555 (kept)-$860-$580-$675+$9,399
+$1,944/mo
+$7,364
+$1,523/mo
69%+$8,634$47,049$157.03+476

Cost of waiting

The BEST roll done later instead of today (-$7,761 at mid). Black-Scholes at each leg's IV, aged and moved, anchored on today's market. Estimates.
Roll onDays before expirySpot -30% ($93)Spot +0% ($134)Spot +30% ($174)
Today448--$7,761-
2027-10-2390-$8,406-$5,837-$3,280
2027-12-0745-$8,382-$6,180-$2,185

How much time to buy

FamilyExpiryLCSPHPCash midHedge estMargin chgExtra incomeExtra safeRestartValue incl. incomeMax lossCC-SSDelta sh
Jun 16 '28FULLJun 16 '2811018575-$7,761--$3,682+$9,268
+$1,917/mo
+$7,043
+$1,456/mo
68%+$5,190$45,950$158.76+451
Top 25 candidates on Jun 16 '28
FamilyExpiryLCSPHPCash midHedge estMargin chgExtra incomeExtra safeRestartValue incl. incomeMax lossCC-SSDelta sh
1FULLJun 16 '2811018575-$7,761--$3,682+$9,268
+$1,917/mo
+$7,043
+$1,456/mo
68%+$5,190$45,950$158.76+451
2FULLJun 16 '2810018585-$11,611--$3,733+$9,272
+$1,918/mo
+$7,052
+$1,458/mo
68%+$1,394$45,800$158.71+451
3FULLJun 16 '289519090-$11,921--$3,363+$9,295
+$1,922/mo
+$7,108
+$1,470/mo
68%+$738$46,110$158.41+456
4FULLJun 16 '289518590-$13,291--$3,825+$9,274
+$1,918/mo
+$7,057
+$1,459/mo
68%-$192$45,480$158.68+451
5FULLJun 16 '289019095-$13,581--$3,424+$9,299
+$1,923/mo
+$7,116
+$1,472/mo
68%-$858$45,770$158.37+456
6FULLJun 16 '289018590-$14,171--$3,309+$9,303
+$1,924/mo
+$7,127
+$1,474/mo
68%-$1,559$46,360$158.31+456
7FULLJun 16 '289018595-$14,951--$3,886+$9,278
+$1,919/mo
+$7,065
+$1,461/mo
68%-$1,787$45,140$158.64+450
8FULLJun 16 '2890185100-$15,781--$4,542+$9,251
+$1,913/mo
+$7,000
+$1,448/mo
68%-$1,988$43,970$158.98+445
9FULLJun 16 '289018090-$15,671--$3,652+$9,285
+$1,920/mo
+$7,082
+$1,465/mo
68%-$2,734$45,860$158.55+451
10FULLJun 16 '2880190105-$17,421--$3,640+$9,303
+$1,924/mo
+$7,126
+$1,474/mo
68%-$4,478$45,610$158.31+455
11FULLJun 16 '2880185100-$17,891--$3,436+$9,308
+$1,925/mo
+$7,138
+$1,476/mo
68%-$5,147$46,080$158.25+455
12FULLJun 16 '2880185105-$18,791--$4,102+$9,282
+$1,919/mo
+$7,075
+$1,463/mo
68%-$5,407$44,980$158.59+449
13FULLJun 16 '2875190105-$18,271--$3,094+$9,334
+$1,930/mo
+$7,203
+$1,490/mo
68%-$5,843$46,460$157.90+460
14FULLJun 16 '2880185110-$19,811--$4,331+$9,255
+$1,914/mo
+$7,009
+$1,449/mo
68%-$6,225$44,000$158.94+443
15FULLJun 16 '2880180100-$19,391--$3,779+$9,289
+$1,921/mo
+$7,093
+$1,467/mo
68%-$6,323$45,580$158.49+450
16FULLJun 16 '2875190110-$19,291--$3,323+$9,309
+$1,925/mo
+$7,141
+$1,477/mo
68%-$6,659$45,480$158.23+454
17FULLJun 16 '2875185105-$19,641--$3,555+$9,314
+$1,926/mo
+$7,154
+$1,479/mo
68%-$6,772$45,830$158.16+454
18FULLJun 16 '2875185110-$20,661--$3,784+$9,288
+$1,921/mo
+$7,090
+$1,466/mo
68%-$7,589$44,850$158.50+448
19FULLJun 16 '2875180100-$20,241--$3,233+$9,321
+$1,928/mo
+$7,172
+$1,483/mo
68%-$7,687$46,430$158.07+455
20FULLJun 16 '2875180105-$21,141--$3,898+$9,296
+$1,922/mo
+$7,109
+$1,470/mo
68%-$7,947$45,330$158.41+449
21FULLJun 16 '2875185115-$21,691--$4,277+$9,262
+$1,915/mo
+$7,026
+$1,453/mo
68%-$8,152$43,880$158.85+442
22FULLJun 16 '2875175100-$21,781--$3,535+$9,303
+$1,924/mo
+$7,127
+$1,474/mo
68%-$8,943$45,970$158.31+449
23FULLJun 16 '2870190115-$21,501--$3,235+$9,311
+$1,926/mo
+$7,146
+$1,478/mo
68%-$8,955$45,690$158.20+452
24FULLJun 16 '2870185110-$21,841--$3,204+$9,316
+$1,927/mo
+$7,158
+$1,480/mo
68%-$9,322$46,030$158.14+453
25FULLJun 16 '2870185115-$22,871--$3,696+$9,290
+$1,921/mo
+$7,096
+$1,467/mo
68%-$9,884$45,060$158.48+447
How this was built