Double Diagonal

Volatility Strategies Advanced Singapore STI DBS OCBC UOB SINGTEL

Neutral - Expecting Range-Bound with Time Decay

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Quick Reference

Strategy Type Diagonal Spreads on Both Sides (Puts and Calls)
Market Outlook Neutral - Expecting Range-Bound with Time Decay
Risk Profile Defined Risk - Complex Multi-Expiration Structure
Reward Profile Profits from Time Decay Differential Between Expirations
Time Horizon Front Month: 30-45 DTE; Back Month: 60-90 DTE
Iv Environment Moderate IV; Benefits from IV Differential
Breakeven Dynamic - Changes as Front Month Decays

Payoff Profile

A double diagonal has a tent-shaped payoff similar to an iron condor but with time spread characteristics. The payoff is dynamic and changes as the front month approaches expiration. • Achieved if stock stays between short strikes at front expiration • Limited but complex - depends on where stock is and IV levels • Between short strikes; widens as front month decays • Profit zone expands as front month theta accelerates

Singapore Market Details

Primary Instruments STI Options, DBS, OCBC, UOB - need multiple expiration months
Mas Compliance MAS regulated; margin based on position risk
Contract Size 1,000 shares for equities; S$5 per point for STI
Trading Hours 9:00 AM - 5:00 PM SGT
Expiration Availability Monthly expirations only - limits diagonal flexibility
Strike Intervals S$0.50 for equities; 10-25 points for STI
Settlement T+1 for derivatives; T+2 for equities if assigned
Tax Treatment No capital gains tax for individuals in Singapore
Critical Note Singapore monthly-only options means diagonals span 30-day increments

Frequently Asked Questions

Why would I use a double diagonal instead of just an iron condor?

Double diagonals have lower gamma (less sensitive to movement), long vega (benefit from IV increase), and can be rolled perpetually. Use when you want a longer-term position with less daily P&L volatility.

Why do I have to pay to enter a double diagonal?

Back month options have more time value than front month options. Since you're buying back month (expensive) and selling front month (cheaper), the net is usually a debit. You're paying for reduced gamma risk.

What happens at front month expiration?

If stock is between shorts, they expire worthless (good). You then either close the back month longs to exit, or sell new front month shorts against them to continue. Plan before expiration.

Can I trade double diagonals in Singapore?

Yes, but Singapore only has monthly expirations. Your front-to-back gap will always be approximately 30 days. This works fine but limits flexibility compared to markets with weeklies.

What if the stock moves beyond my short strikes?

The tested short will be ITM, but your back month long provides some protection. You'll have a loss, but it's limited. The back month long partially offsets the short's loss.

How does the vega exposure affect my position?

You're long vega, so IV increases help and IV decreases hurt. If you expect a volatility event, the double diagonal may benefit. If IV is crushing, your back month longs lose value faster than your shorts.

When should I roll vs close entirely?

Roll if your outlook remains range-bound and term structure is favorable. Close if: (1) You've hit profit target, (2) Outlook has changed, (3) Term structure is unfavorable, (4) One side is deeply tested.

How do I adjust a tested double diagonal?

Options include: Roll the tested short further OTM, close the entire tested diagonal side, add protection by buying closer long, or close the whole position. Choose based on conviction and cost.

What's the ideal DTE combination for Singapore?

With monthly-only options, use front month at 30-45 DTE and next month (back) at 60-75 DTE. This gives good theta differential while maintaining the time spread benefit.

How does a double diagonal compare to a double calendar?

Double diagonal has DIFFERENT strikes (shorts closer to money, longs further OTM). Double calendar has SAME strikes (pure time spread). Diagonal has wider profit zone but more complex payoff.

How do I optimize the theta-to-vega ratio?

Front month shorts closer to ATM increase theta. Back month longs further OTM decrease vega. Fine-tune strike selection to maximize theta while keeping vega at acceptable level for your view.

When is term structure inversion a trading signal?

Inversion (front > back IV) often signals fear or event premium. For existing positions, consider closing as the structure is unfavorable. For new entries, wait for normalization unless you specifically want that exposure.

How do I run a perpetual double diagonal program?

Establish rules: entry term structure, DTE triggers for rolling (e.g., 10 DTE), profit/loss targets per cycle, and sizing. Roll systematically - when front reaches trigger, close front and sell new shorts against back, then add new back longs.

How do double diagonals fit in a portfolio with iron condors?

They provide diversification: DD long vega vs IC short vega, DD lower gamma vs IC higher gamma. Consider allocating 60-70% to ICs and 30-40% to DDs for balanced volatility exposure.

What variations work for directional bias?

Unbalanced DD: More contracts or closer strikes on favored side. Skip-strike DD: Wider gap on less-favored side. Can also run single diagonal on favored side with IC characteristics on other.

Related Strategies

Iron Condor Double Calendar
Diagonal Spread (Single)

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