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MT44(Newbie)Newbie
1 May 2026

Apologies - couldn't really find a clear answer (that I understood :) ) to this in previous posts.

I have options granted by my employer, which vested at the time the agreement with them was signed - at that time the market value of each share was less than the vesting price (~30% less).

Fast forward, and the market price now significantly exceeds the offer price, so it's becoming worthwhile to exercise the options - for argument's sake, let's say $1.00 market vs $0.25 option price.

Several-fold question:

  1. AIUI, if i exercise the options e.g. now, and dispose of within 30 days, then I will simply have the ESS tax hit at the marginal rate i.e. effectively 47%?
  2. if i exercise now, and dispose of e.g. in 6 months time, would that result in tax for the current financial year based on the 'income' of the price discount for acquiring the shares + CGT when i dispose of 6 months down the track?
  3. as per previous + I hold onto the shares for > 12 months, so 50% CGT discount applies?
  4. or am I overthinking this, and I'm not effectively going to be taxed twice if I don't dispose of them within 30 days?


Many Thanks

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ATO Certified Response
NikkiATO(Community Moderator)Community Moderator
ATO Certified Response5 May 2026

Hi @MT44,


ESS tax outcomes depend on the type of scheme you’re in and when the taxing points occur, so there isn’t a single answer that applies in all cases.


Under tax‑deferred ESS schemes, the discount on options or shares isn’t taxed until the ESS deferred taxing point happens. This is usually when restrictions lift, the options are exercised (for rights), or a maximum time period is reached.


If you dispose of the shares within 30 days of the deferred taxing point, the taxing point shifts to the date of disposal (the 30‑day rule). In that case, the ESS discount is still taxed as ordinary income, and CGT generally doesn’t apply.


If you hold the shares beyond the 30‑day window, the ESS discount is assessed at the deferred taxing point, and any further increase in value after that is dealt with under the capital gains tax (CGT) rules when you later dispose of them.


For CGT purposes, shares acquired under a tax‑deferred ESS are taken to be re‑acquired at the deferred taxing point, which is when the CGT holding period starts for the 12‑month discount.


If you’re still unsure after checking your ESS statements or plan rules, a registered tax agent can help apply the rules to your specific arrangement.

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