Your covered call expired yesterday. You think it expired worthless. Then your broker sends a notification: "You've been assigned on 100 shares of VTSAX."
You didn't expect this because the stock closed at $147 and your call was a $148 strike. You thought $1 out of the money meant safety. You didn't check the ex-dividend date: the stock was ex-dividend $1.02 that same day. Investors exercised early to capture the dividend.
This is exactly why options assignment tracking matters. Assignment isn't some distant risk—it's your portfolio's reality. You need a system that predicts when it will happen, alerts you before it does, and helps you manage the consequences.
Why Assignment Tracking Breaks Most Traders
Here's the problem: brokers don't force you to think about assignment. Your app shows an expiring option, but it doesn't say "This will likely be assigned because we're in dividend capture territory."
Most traders stumble into the following mistakes:
1. Surprise Assignment on Dividend Dates You sell a $50 call. The stock is worth $49. Should be safe. But if an ex-dividend date is approaching, the stock owner might exercise the call early to capture the dividend, triggering assignment you didn't anticipate.
2. Multi-Leg Assignment Chaos You're selling puts and holding covered calls on the same stock. Your put gets assigned (forcing you long), and simultaneously your covered call gets assigned (forcing you short). Now you have contradictory positions or forced liquidations.
3. Cascading Expirations All 5 of your covered calls expire the same week. If 4 get assigned, you're suddenly short 400 shares of capital and need to decide whether to buy them back, hold naked short, or deploy cash. Your portfolio restructuring was forced, not planned.
4. Margin Calls You sold puts that got assigned, which now requires capital you didn't set aside. Or you had early assignment on a cash-secured put right before a major expense. Margin calls happen when assignment tracking is bad.
5. Tax Confusion You sold a call for $2 premium, got assigned, and sold at the strike. Your broker now has a complicated cost-basis entry. If you didn't track the assignment as a taxable event, your tax reporting becomes nightmarish.
The Assignment Tracking Framework
You need to track four things for each option position:
Expiration Clustering (1) When do your options expire? Do multiple positions expire on the same day?
Expected Assignments This Week:
January 31, 2026:
- VTSAX 100 shares @ $148 call (likely: 15% probability)
- VTI 200 shares @ $220 call (likely: 8% probability)
- SOXX 50 shares @ $380 put (unlikely: 2% probability)
February 7, 2026:
- SPY 50 shares @ $450 call (likely: 22% probability)
If both VTSAX and VTI expiring same day, you need $21,000 liquid to accept both assignments. If you don't have it, you need to decide now: buy one back, or sell other positions.
Dividend Capture Risk (2) This is the #1 reason for unexpected early assignment.
Dividend Capture Assessment:
VTSAX 100 shares, $148 call:
- Stock price: $147 (ITM by $1)
- Ex-dividend date: Jan 30 ($1.02)
- Call expires: Jan 31
- RISK: HIGH (stock owner will likely exercise to capture dividend)
- Action: Plan for assignment by Jan 30
VTI 200 shares, $220 call:
- Stock price: $215 (OTM by $5)
- Ex-dividend date: Feb 15
- Call expires: Jan 31
- RISK: NONE (expires before ex-dividend)
- Action: No early assignment risk
Most brokers provide ex-dividend data in their tools. Bookmark this: Always cross-reference expiration dates with ex-dividend dates.
Assignment Probability Estimation (3) For each option, estimate the likelihood of assignment based on intrinsic value:
- Deep ITM (In The Money by $2+): 80–100% probability of assignment
- Slightly ITM (In The Money by $0–$2): 20–50% probability of assignment
- At or Near The Money: 5–15% probability of assignment
- OTM (Out of The Money): less than 1% probability of assignment
This helps you prioritize. The VTSAX $148 call with stock at $147 (slightly ITM) might not be guaranteed assignment, but it's high-risk.
Capital Requirement Planning (4) If assignments happen simultaneously, do you have enough cash?
Total Capital Required for Simultaneous Assignment:
VTSAX: 100 × $148 = $14,800
VTI: 200 × $220 = $44,000
SOXX: 50 × $380 = $19,000 (short sale, credit required)
Total: ~$73,800 capital needed
Current available: $50,000
Shortfall: $23,800
Action: Close SOXX put to reduce cash requirement, or plan to sell other holdings.
Building Your Assignment Tracker
Tier 1: Daily Monitoring (Expiration Alerts)
Every morning, check:
- How many days until expiration?
- Which positions are ITM and likely to be assigned?
- Any ex-dividend dates today or tomorrow?
- Do I have cash to accept all assignments if they happen simultaneously?
Tier 2: Weekly Expiration Planning (7-Day Lookahead)
Every Friday, ask:
- What expires next week?
- What's my expected capital requirement?
- Do I need to close, roll, or buy back any positions?
- Any dividend captures coming?
Tier 3: Monthly Assignment Summary
Track actuals vs. predictions:
- How many positions were assigned last month?
- How many of my predictions were correct?
- Did any assignments surprise me?
- What will I do differently next month?
A Real Tracking Example
Let's say you have the following portfolio expiring this month:
| Position | Expires | Strike | Stock Price | ITM/OTM | Dividend Risk? | Assignment Probability | Action Required |
|---|---|---|---|---|---|---|---|
| VTSAX 100 × $148 call | Jan 31 | $148 | $147 | $1 ITM | HIGH (ex-div 1/30, $1.02) | 60% | Close or accept |
| VTI 200 × $220 call | Jan 31 | $220 | $215 | $5 OTM | None | 3% | Hold to expiration |
| SOXX 50 × $380 put | Jan 31 | $380 | $378 | $2 ITM | None | 25% | Consider closing |
| SPY 50 × $450 call | Feb 07 | $450 | $445 | $5 OTM | None | 8% | Hold to expiration |
Analysis:
- VTSAX call is assignment-imminent. Plan for $14,800 capital deployment by Jan 29.
- SOXX put has moderate assignment risk. If both VTSAX and SOXX are assigned, you need $14,800 + $19,000 = $33,800 cash.
- SPY and VTI are unlikely to assign before expiration.
Decision:
- Accept VTSAX assignment (plan capital)
- Close SOXX put to reduce cash requirement and eliminate uncertainty
- Hold VTI and SPY calls
The Hidden Costs of Poor Assignment Tracking
1. Forced Liquidations You don't have cash to accept assignment, so you're forced to sell other positions at inopportune times. That "good" dividend holding becomes a forced sale at a loss.
2. Assignment Surprise → Tax Problems Early assignment triggered a short-term capital gain that you should've planned for. Now you owe more tax than expected or have wash-sale complications.
3. Opportunity Cost Your assigned shares are held for 6 months at breakeven when you could've redeployed that capital elsewhere.
4. Mental Fatigue Every day you wake up wondering "Will I be assigned today?" instead of systematically managing it.
Assignment Tracking Tech Stack
Option 1: Spreadsheet (Best for ≤10 positions)
- Google Sheets with formulas tracking days to expiration
- Manual entry of stock prices and assignment tracking
- Free, but requires daily discipline
Option 2: Broker Tools (Better for ≤30 positions)
- Most brokers (TD Ameritrade, Interactive Brokers, Tastyworks) have built-in expirations calendars
- Set alerts for expirations 5 days before expiry
- Bonus: Early assignment notifications
- Limitation: Can't aggregate across strategies
Option 3: Dedicated Options Tracking Software (Best for 30+ positions)
- OptionStrat, Portfolio Lab, Tastytrade analytics
- Real-time assignment probability calculations
- Automated alerts
- Higher cost ($20–50/month typically)
Option 4: Custom API Scripts (Best for serious traders)
- Pull data from Interactive Brokers API
- Custom assignment logic and predictions
- Automated alerts to your phone
- Requires coding skills
Start with your broker's tools. Move to software when manual management becomes a 1-hour daily task.
Assignment Tracking Checklist
Before each expiration:
- ✅ What's the stock price relative to strike?
- ✅ What's the ex-dividend date?
- ✅ What's my assignment probability?
- ✅ Do I have cash if assigned?
- ✅ What's my plan (close, roll, or accept)?
- ✅ Will assignment create tax issues?
- ✅ Will I be forced to liquidate other positions?
The Bottom Line
Assignment isn't something that happens to you—it's something you anticipate and manage. The traders who've mastered options aren't the ones with the fanciest strategies; they're the ones who know, on January 15, exactly which of their positions will be assigned on January 31.
Build your assignment tracking system now. It takes 30 minutes to set up a basic spreadsheet. It will save you from a $20,000 forced liquidation, a margin call, or a tax nightmare. That math is easy.