Should I Sell Before 30 June 2027? CGT Reform Decision Guide for Investors

General information only. This is not tax or financial advice. Consult a registered tax agent for advice specific to your situation.

Walk into any investor Facebook group, Reddit thread, or accountant’s waiting room in the second half of 2026 and you’ll hear the same question on a loop: Should I sell before 30 June 2027 to lock in the 50% CGT discount? It is, by some margin, Australia’s most-searched investment question of the post-Budget cycle — and it has a deceptively simple answer.

For most people the answer is no. Selling an asset purely to dodge a tax change usually destroys more long-term value than it saves, especially once you factor in transaction costs, opportunity cost, and the fact that the new rules don’t blow up everyone’s tax bill — they shift it. But for a specific subset of investors, the 14 months between now and 30 June 2027 is a genuine planning window worth running through a calculator.

This guide walks you through the decision in plain Aussie English: a five-question framework, the timeline that matters, the math that decides it, and four worked examples covering the most common situations — property, shares, crypto, and a small business owner near retirement. By the end you should know whether you’re a “consider accelerating” or a “stop overthinking and just hold” case.

The short version: Selling solely for tax reasons usually destroys more value than it saves. Accelerate ONLY if (a) you were already planning to sell within 1–2 years anyway, (b) your post-reform tax exposure is significant, or (c) you’re in a low-MTR window now that will reverse later. Otherwise: hold. Transaction costs, the opportunity cost of forgone returns, and the indexation half of the reform (which actually shelters inflation) all argue against panic selling.

For the cross-asset overview and Treasury’s source examples, see the master article: 50% CGT Discount Reform: Cost Base Indexation + 30% Minimum Tax from 1 July 2027. For asset-specific deep dives, see the property, shares, ETFs, crypto, and small business companion articles linked at the bottom.

The five-question decision framework

Most “should I accelerate?” questions resolve in under five minutes if you work through these five gates in order. If you answer NO at any gate, the answer is almost always “don’t accelerate, just hold.” If you answer YES across most of them, run the numbers in the CGT Scenario Compare tool before acting.

Q1 — Were you already planning to sell this asset within the next 1–2 years anyway?

This is the single most important question. If your existing plan was to sell in 2028, 2029, or beyond, accelerating means bringing a tax event forward by years — paying tax now that you wouldn’t have paid for ages, and giving up however many years of compounding on the after-tax-now proceeds. That trade rarely wins.

If your plan was already to sell in 2027 or early 2028 — to fund a retirement, a house deposit, a business buy-in, a divorce settlement — then 30 June 2027 is a deadline you can use to your advantage. The discount preservation is essentially free in this case.

Q2 — Will the asset’s post-2027 portion of gain be large?

For an asset you’ve owned for 15 years already, the reform-portion of any gain on a sale in 2029 is small (most of the hold is pre-reform). For an asset bought in 2025 and sold in 2035, the reform portion dominates. The bigger the reform share, the more the 50% discount is worth locking in.

A quick estimate: divide pre-1-July-2027 days by total days held at expected sale date. If that legacy share is above ~75%, the reform impact is muted and accelerating is rarely worth it. Below ~40%, the reform portion bites and accelerating starts to make sense — IF Q1 also says yes.

Q3 — Will your marginal tax rate be 30% or below in 2026–27, AND higher later?

The 30% minimum tax binds whenever your marginal rate is below 30%. For low-income earners, retirees on small pensions, and people on parental leave or career breaks, this can flip the math: a sale in 2026–27 under the 50% discount might tax the gain at 7.5–15% (low MTR × 50%), while the same gain post-reform attracts the 30% floor.

The opposite case also matters. If you’re climbing into a higher bracket in 2027–28 (promotion, partner returns to work, end of negative gearing), accelerating into the higher MTR year is the wrong call — wait, then sell in the year your marginal rate is lowest.

Q4 — Is the asset subject to a carve-out that already preserves favourable treatment?

Several asset types keep their pre-reform tax position regardless of the 1 July 2027 date:

• Main residence — full exemption unchanged.
• Eligible new residential builds (completion on/after 1 July 2027, held by first taxpayer for up to 15 years) — election between legacy 50% discount and new rules per disposal.
• Small business CGT concessions — 15-year exemption, 50% active asset reduction, retirement exemption, rollover all retained.
• Age Pension and JobSeeker recipients — exempt from the 30% minimum in years they realise a gain.

If your asset sits in any of these buckets, there is no benefit to accelerating just because of the CGT reform — the carve-out already shields you.

Q5 — Are transaction costs prohibitive relative to the tax saving?

Selling and re-establishing the same investment position isn’t free. For ASX shares you’ll pay 0.1–0.2% brokerage round-trip plus the bid-ask spread. For an ETF, similar. For an investment property, 5–7% of the sale price in agent commission, marketing, legal fees, plus stamp duty if you re-purchase — that’s $50,000+ on a $1 million sale, before you’ve even thought about tax.

If your modelled tax saving from accelerating is smaller than your transaction-cost cliff, the saving is illusory. The reform has to bite you by more than the friction cost just to break even.

Score yourself. A “yes” on Q1 plus a “yes” on either Q2 or Q3, with NO on Q4 and Q5, makes accelerating a serious candidate. Anything less and the default answer is “hold.” Run a tie-breaker in the CGT Scenario Compare tool — it shows the full Bucket A vs Bucket B side-by-side under your actual numbers.

Timeline — the dates that decide which rules apply

Date	What happens	Why it matters
12 May 2026	Budget 2026 announces CGT reform. No legal effect yet.	Markets price in the change; investors start planning.
From 12 May 2026	Integrity rules apply. Treasury has flagged sham transactions designed to shift gains across the 1 July 2027 line for review.	Normal arm’s-length sales unaffected. Artificial wash-sales and back-dated contracts will be challenged.
30 June 2027 (Wed)	Last day for a SETTLED disposal under the full 50% discount. Contract date governs CGT event A1 (shares, property); the gain you crystallise under contract on/before this date stays in Bucket A. Settlement timing matters separately for cash receipt.	This is THE deadline. If you genuinely want to accelerate, your contract must be signed by 30 June 2027. Cutting it fine is risky — get conveyancing and broker confirmations in writing.
1 July 2027	Reform begins. Cost base indexation + 30% minimum tax apply to gains accruing from this date. Pre-1985 assets become CGT-able for the first time.	Any asset still held becomes a Bucket B (split treatment) holding the moment this date passes.
30 June 2028	First full reform-period income year ends.	Self-lodgers face the new rules for the first time on their 31 October 2028 return.
30 June 2032	Five years past reform. Early data emerges on whether revenue projections were met and whether the reform behaves as Treasury modelled.	First realistic window for the legislature to revisit or amend the settings.

The key practical point: 30 June 2027 is a contract-date deadline, not a settlement-date deadline, for shares, crypto, and most other CGT events. Property is the awkward exception — see the property article for the contract-vs-settlement detail. For most investors, “sell before 30 June 2027” means “have a binding sale contract signed and dated on or before 30 June 2027.”

Heads up: The contract date controls CGT event A1 for shares and most asset types. For property the contract date also controls the CGT event, but settlement controls when cash actually arrives — which matters for your other financial planning. Either way, do not assume that a contract signed late June with settlement deep into July keeps you on the legacy side of the line. Get it in writing from your conveyancer or broker.

How time changes your tax bill — accelerated vs delayed sale

The whole “should I accelerate?” question reduces to one comparison: tax under Bucket A (sell before 30 June 2027) versus tax under Bucket B (split treatment if you sell after), plus the opportunity cost of crystallising tax 12 months early. Both pieces matter; people who panic-sell typically remember the first and forget the second.

Sensitivity 1 — Bucket A vs Bucket B, by holding period and growth rate

Imagine a $200,000 nominal gain on an asset bought 1 July 2020. The taxpayer’s marginal rate is 39% (includes Medicare). Compare selling on 30 June 2027 (Bucket A) to selling 12 months later, 30 June 2028 (Bucket B with a 7-year hold and 1-year reform period), assuming 2.5% CPI and continued asset growth at the rate shown:

Growth rate	Nominal gain by Jun 2028	Bucket A tax (30 Jun 2027)	Bucket B tax (30 Jun 2028)	Bucket B − Bucket A
4%/yr nominal	~$215,000	$39,000	~$43,400	+$4,400
7%/yr nominal	~$226,000	$39,000	~$45,400	+$6,400
10%/yr nominal	~$235,000	$39,000	~$47,200	+$8,200

Plain English: waiting one extra year typically costs $4,000–$8,000 in extra tax on a $200k gain, depending on growth rate. But you also got an extra year of price appreciation — at 7% nominal growth that’s roughly $26,000 of extra gain in your pocket (~$10,000 after tax). The math here favours waiting — even with the reform-portion penalty, the forgone year of growth is bigger.

Sensitivity 2 — How much do I save by selling 12 months early?

The reverse view: what if accelerating from a planned 2028 sale to a 2027 sale saves you the entire reform-portion tax? Use a $500,000 nominal gain, 45% marginal rate, 5-year hold:

Scenario	Bucket A tax (30 Jun 2027)	Bucket B tax (30 Jun 2028)	Saving by accelerating
5-yr hold, sale planned 30 Jun 2028 anyway	$112,500	~$117,800	~$5,300
5-yr hold, sale planned 30 Jun 2032 anyway	$112,500	~$155,000 (mostly reform)	~$42,500
10-yr hold, sale planned 30 Jun 2030 anyway	$112,500	~$120,000	~$7,500

Plain English: the saving from accelerating is small if your planned sale is just 12 months away (most of the gain is legacy anyway in Bucket B). It grows materially if your planned sale is 4+ years away (more of the gain falls in the reform bucket). But — and this is the catch — accelerating from 2032 to 2027 means paying tax five years early and giving up five years of compounding on the asset.

Sensitivity 3 — The 30% minimum tax cliff for low-MTR holders

For a retiree on a 16% effective marginal rate (low taxable income, SAPTO offsets), accelerating BEFORE the 30% minimum kicks in can save real money:

Sale timing	Discount	Effective rate	Tax on $100k gain
30 Jun 2027 (Bucket A)	50%	16% × 50% = 8%	$8,000
30 Jun 2030 (Bucket B, 3-yr reform)	Split: ~50% legacy, 50% reform with 30% floor on reform half	(16% × 50% × 0.5) + (30% × 0.5 × indexed) ≈ 19%	~$19,000
30 Jun 2034 (Bucket B, 7-yr reform)	Split: ~30% legacy, 70% reform	~25%	~$25,000

Plain English: the 30% minimum hurts low-MTR holders specifically. For a high-MTR taxpayer (45%) the math is closer to a wash because their marginal rate is above 30% either way. For a retiree, the 30% floor materially changes the picture — sometimes by 2× or more on the post-reform portion.

Sensitivity 4 — When growth rate flips the answer

For very slow-growth assets (returns near or below CPI), the indexation half of the reform actually shelters more of your gain than the 50% discount used to. A 3.5%/year nominal asset held 8 years past 1 July 2027 has roughly half its gain absorbed by indexation — sometimes more than 50% discount would have done. Accelerating these assets to “lock in the discount” is exactly the wrong move; you’d be locking in a worse outcome.

The rule of thumb from Treasury’s modelling: real returns above ~5% per year produce more tax under the new rules; below ~2.5% produces less tax. Slow-grow regional property, bond ETFs, defensive infrastructure shares, low-yield rural land — these are the assets where the reform is net friendly, and accelerating is value-destroying.

Worked example 1 — Property investor where accelerating makes sense

Steve owns an investment unit in Brisbane’s inner-north. He bought it for $500,000 in March 2017 with $25,000 of stamp duty and legal costs (cost base $525,000). It’s now valued at $850,000 in May 2026 — a paper gain of $325,000 after nine years. Steve’s marginal rate is 39% (includes Medicare). Importantly, he was already planning to sell in 2028 or 2029 to fund his daughter’s first-home deposit and pay down his own home loan.

He’s looking at two scenarios.

Option A — Accelerate, sell 30 June 2027

• Holding period at sale: 10 years 3 months. Bucket A.
• Estimated value at 30 Jun 2027 (continued 4% growth): $880,000.
• Cost base: $525,000.
• Nominal gain: $355,000.
• Discounted gain (50%): $177,500.
• Tax at 39%: $69,225.

Option B — Stick to the original plan, sell 30 June 2029

• Holding period at sale: 12 years 3 months. Bucket B.
• Estimated value at 30 Jun 2029 (continued 4% growth): $920,000.
• Cost base: $525,000.
• Nominal gain: $395,000.
• Hold split: pre-1-July-2027 days = 3,759; total days = 4,489 → 83.7% legacy / 16.3% reform.
• Legacy portion: $395,000 × 83.7% = $330,615. Discounted: $165,308. Tax at 39% = $64,470.
• Reform portion: $395,000 × 16.3% = $64,385. CPI uplift (2 years at 2.5%/yr ≈ 1.051): indexation adjustment ≈ $3,124. Real reform gain ≈ $61,261. Tax at 39% = $23,892.
• Total Bucket B tax: $88,362.
• Plus 2 extra years of rental income (net of expenses, say $8,000/yr after expenses) = +$16,000 in his pocket.

The verdict

Tax-only comparison: Option A saves ~$19,000 in CGT. But Option B gives him 2 extra years of rental cash flow worth ~$16,000 net. Net advantage of accelerating: ~$3,000.

Recommendation: borderline. If Steve’s rental net income is closer to $5,000/yr after expenses, accelerating wins by ~$9,000. If it’s closer to $10,000/yr, the two options are within rounding. The right call depends on his specific rental yield and his own cash-flow needs. The math here is too close to make purely on tax grounds — non-tax factors decide it. If he hates being a landlord, accelerate. If the rental is humming, hold.

Worked example 2 — Share investor where accelerating is the wrong move

Naomi holds 1,000 CBA shares. She bought them in 2020 at $80 each — cost base $80,000 (plus negligible brokerage). They’re now worth $145 each as of May 2026 — paper value $145,000, paper gain $65,000. Naomi is a high-income GP on a 45% marginal rate. She has no plans to sell — these are part of her long-term retirement portfolio she intends to hold for another 15+ years.

She’s wondering whether she should panic-sell and re-buy to lock in the 50% discount.

Option A — Sell and re-buy on 30 June 2027

• Tax on $65,000 gain (Bucket A): $65,000 × 50% × 45% = $14,625.
• Plus brokerage round-trip (0.15% × $145,000 sell + 0.15% × $145,000 buy) ≈ $435.
• Plus bid-ask spread (assume 0.05% each way) ≈ $145.
• New cost base post-rebuy: $145,000.
• Cash burned now: $15,205 (tax + costs).

Option B — Hold the original parcel through to 2035 (planned 15-year hold)

• Hold spans 1 July 2020 → 1 July 2035 = 5,479 days. Pre-reform: 2,557 days = 46.7%. Reform: 53.3%.
• Assume 6%/yr nominal growth → value 2035 ≈ $347,500. Gain $267,500.
• Legacy portion: $267,500 × 46.7% = $124,923. Discounted: $62,461. Tax at 45% = $28,108.
• Reform portion: $267,500 × 53.3% = $142,577. CPI uplift (8 yrs at 2.5%): indexed factor 1.218 → indexation $25,544. Real gain $117,033. Tax at 45% = $52,665.
• Total Bucket B tax: $80,773.

Option C — Option A, then hold the re-bought parcel to 2035

• Tax paid in 2027 (Option A): $14,625 + $580 costs = $15,205.
• After re-buy: cost base $145,000, held 8 years to 2035, wholly reform (Bucket C). Value $347,500. Gain $202,500. CPI uplift over 8 yrs at 2.5% ≈ 1.218 → indexation $36,295. Real gain $166,205. Tax at 45% = $74,792.
• Total tax across both events: $14,625 + $74,792 = $89,417. Plus $580 friction.

The verdict

Option B (just hold) total tax: $80,773. Option C (accelerate and re-buy) total tax + friction: $89,997.

Accelerating costs Naomi roughly $9,200 over the lifecycle. Why? Because resetting the cost base loses her 7 years of legacy-bucket accrual. The pre-2027 portion of her gain — taxed at the much friendlier 50% discount — disappears the moment she sells and re-buys. The “win” of locking in the 2027 discount on her current $65k gain is more than offset by the loss of legacy treatment on the next $137k of growth.

Recommendation: HOLD. This is the most common case across the share investor cohort and the one that gets the wrong answer most often in social media discussion. Wash-selling to “lock in the discount” mathematically destroys value for any investor with a multi-year hold horizon. The legacy bucket is a one-time gift — burning it through a tax-motivated round-trip is the most expensive mistake an otherwise rational holder can make.

(Treasury’s anti-avoidance signalling is squarely aimed at coordinated, multi-asset wash-sale arrangements — not Naomi’s hypothetical case — but the math punishes her plenty without needing the ATO’s help.)

Worked example 3 — Crypto investor with concrete sale plans

Daniel holds 2 BTC, bought in March 2019 at $7,500/BTC (cost base $15,000 total, including small brokerage). At May 2026 the spot price is $185,000/BTC — paper value $370,000, paper gain $355,000. Daniel earns $145,000 salary, putting his marginal rate at 39%. He’s been planning for two years to liquidate one BTC to put a 20% deposit on a house, ideally in late 2027 or early 2028.

The reform announcement reframed his thinking. Should he accelerate the sale?

Option A — Accelerate, sell 1 BTC on 30 June 2027

• Assume BTC price flat at $185,000 (highly uncertain — crypto’s volatility makes any forward estimate suspect).
• Cost base for 1 BTC: $7,500.
• Nominal gain: $177,500.
• Bucket A — 50% discount.
• Discounted: $88,750. Tax at 39%: $34,613.
• Cash to deposit: $185,000 sale − $34,613 tax = $150,387 available.

Option B — Hold to 30 June 2028 (Bucket B)

• Hold spans March 2019 → 30 Jun 2028 = ~3,400 days. Pre-reform: 3,036 days = 89.3%. Reform: 10.7%.
• Assume flat price → gain still $177,500.
• Legacy portion: $158,508. Discounted: $79,254. Tax at 39% = $30,909.
• Reform portion: $18,992. CPI uplift (1 year at 2.5%): negligible, ~$463. Real gain $18,529. Tax at 39% = $7,226.
• Total Bucket B tax: $38,135.
• Cash to deposit: $185,000 − $38,135 = $146,865.

Option C — Hold to 30 June 2031 (Bucket B, longer reform period)

• Hold spans March 2019 → 30 Jun 2031 = ~4,495 days. Pre-reform: 3,036 days = 67.5%. Reform: 32.5%.
• Assume flat → gain $177,500.
• Legacy: $119,813. Discounted: $59,906. Tax: $23,363.
• Reform: $57,688. CPI uplift (4 yrs at 2.5%): factor 1.104 → indexation $5,427. Real gain $52,261. Tax at 39% = $20,382.
• Total: $43,745.
• Cash to deposit: $185,000 − $43,745 = $141,255.

The verdict

Tax saving from accelerating from 2028 plan to 2027 plan: ~$3,500. Tax saving from accelerating from 2031 plan to 2027 plan: ~$9,100.

Both are real but modest, given the size of the gain. The bigger consideration is BTC price volatility: a 10% adverse move between May 2026 and June 2027 wipes out the tax saving 4× over. A 10% favourable move makes the wait worth far more than the tax cost.

Recommendation: accelerate IF the sale was already imminent (within 12 months) AND Daniel’s tolerance for price risk is low. Crypto investors who were going to sell anyway in 2027–2028 should view 30 June 2027 as a small but real tailwind. Crypto investors with no concrete sale plans should NOT accelerate — the volatility of the asset dwarfs the reform impact.

The asset-specific complications (multiple parcels, FIFO/specific-identification matching, staking-reward cost-base proliferation) are covered in detail in the CGT Reform for Crypto companion article.

Worked example 4 — Small business owner who must NOT accelerate

Mei owns and operates a metal fabrication workshop in Geelong, trading through her own company. She also owns the commercial premises in her own name (cost base $420,000, current value $1,250,000, owned since 2010). She’s 52 and plans to retire and sell the business — including the premises — at age 60. Her marginal rate during operating years is 45%.

Reading the CGT reform news, Mei is tempted to sell the premises early to lock in the 50% discount. This would be the most expensive mistake she could make.

Why? Small business CGT concessions wipe most of the tax — IF she waits

The 15-year exemption under Subdivision 152-B applies when:

• The asset has been continuously owned for ≥15 years (Mei meets this from 2025 onwards),
• The taxpayer is ≥55 years old at the time of disposal,
• The disposal is in connection with retirement, AND
• The taxpayer satisfies the basic conditions (small business entity or $6M maximum net asset value test, active asset test, etc.).

At age 60 and 25 years’ ownership, Mei almost certainly meets all four. Under the 15-year exemption the entire capital gain is exempt from CGT — it doesn’t even flow into assessable income.

Comparison — accelerate vs hold to 60

Option A — Sell now (May 2026), age 52, no 15-year exemption (under 55):

• Cost base $420,000. Sale price (current value) $1,250,000. Nominal gain $830,000.
• Cannot access 15-year exemption (age < 55, not retiring).
• Could access 50% active asset reduction + small business retirement exemption ($500k lifetime cap):
• After 50% active asset reduction: $415,000 taxable.
• Retirement exemption: $500,000 lifetime cap… but only if she contributes to super (she’s <55) or holds in a deemed retirement-exemption arrangement. Complex, partial saving.
• After 50% CGT discount on remaining: $207,500 taxable.
• Approximate tax at 45%: ~$93,375 (plus complications).

Option B — Sell at age 60 (2034), with full 15-year exemption:

• Entire $830,000-plus gain is exempt under Subdivision 152-B.
• Tax: $0.

The verdict

Accelerating costs Mei roughly $90,000 in unnecessary tax, plus probably more once you account for the retirement-funding implications.

Recommendation: DO NOT ACCELERATE. The small business 15-year exemption is the single most generous CGT concession in Australian tax law, and the Budget 2026 reform explicitly preserves it (along with the 50% active asset reduction, the retirement exemption, and rollover relief). Anyone within a few years of age 55 with a qualifying active asset should wait for the 15-year window, full stop. The CGT reform is irrelevant to your tax outcome.

The detailed mechanics — basic conditions, active asset test, $6M MNAV test, $500k retirement exemption interaction — are covered in Small Business CGT Concessions After 2027. The takeaway here is unchanged: never accelerate when a Subdivision 152-B exemption is on the horizon.

Five archetypes — when accelerating helps vs hurts

Putting the four worked examples into a broader taxonomy, five investor profiles cover most of the practical decision space:

1. Property investor planning a sale in 1–2 years anyway — consider accelerating. Steve’s case. If the 2027–28 sale is in the plan regardless of tax, hitting the 30 June 2027 deadline is essentially free upside. Run the numbers — the saving is usually real but small (5-figure dollars on mid-size gains), and the decision turns on whether you can settle in time without rushing the market.

2. Long-term ASX share or ETF holder — HOLD. Naomi’s case. Anyone with a multi-decade investment horizon loses money by triggering a tax-motivated round-trip. The legacy bucket is a free gift that survives any number of post-reform years of holding — burning it through a wash-sale destroys the gift entirely.

3. High-gain crypto with imminent sale plans — consider accelerating. Daniel’s case. The pre-reform portion of a long-held crypto position is so large (most BTC/ETH holders are sitting on 5–10 year legacy hold) that even a 10–20% reform share saves real tax. Combined with the actual intention to sell soon for housing/lifestyle reasons, the math points to accelerating. Volatility risk is the wild card — if you can’t stomach a 12-month price swing, lock it in.

4. Small business owner near the 15-year retirement exemption — HOLD. Mei’s case. The 15-year exemption is preserved. Anyone within 5 years of age 55 with a qualifying active asset gets to zero CGT on the lot — there is no possible scenario where accelerating beats that. Same applies to spouses entering retirement together where the asset is owned jointly.

5. Retiree on low MTR with significant unrealised gains — consider accelerating. The 30% minimum is specifically designed to remove the “sell in a low-income year” play that retirees used to be able to engineer. Crystallising gains in 2026–27 (or even better, spread across 2025–26 and 2026–27) under the legacy 50% discount, while the retiree is still at a 16–22% effective marginal rate, can save 8–15 percentage points of effective tax compared to selling after the 30% floor kicks in. This is the cleanest “accelerate” archetype in the cohort.

Heads up: Even within the “consider accelerating” archetypes, transaction costs and opportunity cost can flip the answer. Always run your specific numbers through the CGT Scenario Compare before pulling the trigger on a sale that wasn’t already planned.

Settlement-date and contract-date traps

The 30 June 2027 deadline is a contract date, not a settlement date, for shares, crypto, ETFs, and most CGT events. CGT event A1 triggers on the contract date — that’s when ownership passes for tax purposes.

For property the same rule technically applies (CGT event A1 = contract date), but settlement timing matters separately for cash flow and for some apportionment edge cases. Practically:

• Shares, ETFs, crypto — your trade execution date is your contract date. A trade executed 30 June 2027 sits in Bucket A even if settlement (T+2 for ASX shares) falls in July. A trade executed 1 July 2027 is in Bucket B even if you placed the order on 30 June.
• Property — contract signing date is the CGT event. A property contracted on 28 June 2027 with settlement on 15 July 2027 is in Bucket A. BUT — the ATO has flagged that “sham” contracts back-dated to fall before 30 June 2027 will be challenged. The contract must be genuinely formed by 30 June 2027, with normal arms-length terms, deposits paid, and so on.
• Crypto on overseas exchanges — exchange timezone matters. A trade you execute in Sydney at 11:30pm on 30 June 2027 may show as 1 July 2027 on a US-based exchange’s ledger. The ATO accepts your local timezone for trades you initiated, but get screenshots and document carefully.

Practical advice: if you’re cutting it fine on a major asset sale, get the contract executed at least 1–2 weeks before 30 June 2027 to allow for normal commercial back-and-forth and to avoid disputes about “the contract was conditional and didn’t really form until July.” Solicitors, conveyancers, and brokers will be flat-out the second half of June 2027 — book early.

Transaction cost cliff — the saving has to clear this hurdle

Selling and re-buying an asset to “reset” your cost base under Bucket B (or to lock in the discount in Bucket A and then re-purchase) isn’t free. Approximate friction costs by asset class:

Asset class	Round-trip cost (sell + re-buy)	Notes
ASX shares	0.2–0.4% of value	Brokerage both ways + bid-ask spread; CHESS-sponsored holders pay less
ETFs (ASX-listed)	0.2–0.4%	Same as shares plus tighter bid-ask on liquid ETFs
Managed funds (unlisted)	0.1–1.0%	Buy-sell spread on the fund itself; some have zero spread
Crypto (centralised exchange)	0.4–1.0%	Trading fee both ways plus spread; cold-wallet timing risk
Crypto (DEX, on-chain)	1–3%+	Gas fees, slippage, MEV — much higher friction
Residential investment property	5–8%	Agent commission (2–3%), marketing, legal, plus stamp duty on re-purchase (3–6% depending on state)
Commercial property	6–10%	Higher transaction costs, GST considerations
Vacant land	4–7%	Less liquid; longer marketing periods; valuation disputes

Rule of thumb: if your modelled CGT saving from accelerating is less than 1.5× your friction cost, the saving is illusory once you account for execution risk and timing uncertainty. For property especially, the 5–8% friction means any tax-motivated sale-and-rebuy round-trip is mathematically a loser unless your tax saving exceeds about 8% of the asset value. That essentially never happens.

The corollary: if you’re going to sell-and-rebuy, the sale half is much more defensible than the rebuy half. If you’re crystallising the gain because you wanted to exit anyway, the friction is justified; if you’re crystallising AND re-establishing the same exposure, you’ve paid 5%+ for nothing.

Marginal rate timing — your MTR in 2026–27 vs 2027–28

The CGT discount applies after you’ve added the gain to your other taxable income. So the marginal rate the gain hits at is a function of your other income in the year of disposal. If your other income is variable, the year you sell can change your effective rate materially.

Scenarios where MTR timing matters:

• Promotion incoming. If you’ll be on $180,000+ from July 2027 (top bracket) versus $135,000 in 2026–27 (37% bracket), accelerating into 2026–27 saves 8 percentage points × discounted gain. On a $200k gain, that’s ~$8,000.
• Spouse returning to work. Family income spike in 2027–28 may push you (or your spouse, if jointly held) into the next bracket. Sell in 2026–27 before that happens.
• Career break / parental leave. If you’ll be on $40,000 in 2027–28 (low MTR) but $130,000 in 2026–27 (37% bracket), HOLD. The post-reform discount disappears, but your MTR drop more than compensates.
• Retirement transition. Often misread. The temptation is “sell in 2027 before reform”; the right move for many is to spread sales across the retirement transition (e.g. one parcel in each of 2026–27, 2027–28, 2028–29) to manage MTR and crystallise some legacy + some reform-portion gains under each year’s tax position. Use the CGT Scenario Compare to model multi-year sale strategies.

The 30% minimum interaction matters specifically when your post-reform MTR is below 30%. For a retiree dropping to a 16% effective MTR in 2028 onwards, the 30% floor adds 14 percentage points to the reform-portion tax — large enough that accelerating to the legacy 50% discount in 2026–27 (taxed at 16% × 50% = 8%) easily beats waiting. This is the cleanest accelerate case.

Capital loss harvesting — what’s actually MORE valuable under the new rules

A surprising consequence of the reform: capital loss carry-forwards become MORE valuable, not less.

Here’s why. Under the old rules, a $50,000 capital loss offset a $50,000 gain dollar-for-dollar at the nominal level, before the 50% discount. Net effect: $25,000 less discounted gain × marginal rate. Worth $11,250 at 45% MTR.

Under the new rules, capital losses still offset nominal gain before discount/indexation, but the reform portion is taxed at the greater of MTR or 30%. So the same $50,000 loss saves $50,000 × 30% = $15,000 on a reform-bucket gain (more if the holder is at 45% MTR). The minimum-tax floor effectively raises the marginal value of every dollar of carried-forward loss.

Practical play in 2026–27: if you have unrealised capital losses on under-performing investments, this is the year to crystallise them. The losses carry forward indefinitely under the existing rules (no time limit on capital loss carry-forwards), and they retain their value in pre-reform and post-reform years. They DON’T expire at 30 June 2027.

Use the CGT Harvest Calculator to rank loss-harvest candidates across your portfolio. Anti-wash-sale provisions (Part IVA) still apply — you can’t sell a loss-making stock and re-buy the same stock within 30 days expecting the loss to stick. Substitute exposure (different ticker, different ETF, different asset class) is fine.

Anti-avoidance — don’t try to game the date

Treasury has explicitly flagged that the 1 July 2027 boundary will attract integrity scrutiny. Examples of behaviour likely to be challenged:

• Back-dated contracts. Signing a contract in July 2027 with a 30 June 2027 date on it. This is straightforward fraud and would attract penalty tax + interest, not just a recharacterisation.
• Sham wash-sales. Selling an asset to a related party (your own SMSF, your spouse, your family trust) at a non-arm’s-length price on or around 30 June 2027 to crystallise a gain without genuinely exiting the position. Part IVA general anti-avoidance applies.
• Coordinated portfolio churn. Selling everything you hold on 30 June 2027 and re-buying back the same portfolio on 1 July 2027 (or shortly after) to reset cost bases under the new rules while crystallising legacy discount. Looks too cute by half — the ATO will likely apply the dominant-purpose test and treat the round-trip as a single transaction.
• Bracket-shopping via trust distributions. Distributing a 2026–27 capital gain disproportionately to a low-income beneficiary to capture sub-30% effective rates, where the beneficiary wouldn’t have otherwise received income.

What’s NOT a problem:

• Genuine arms-length sales to unrelated third parties at market price, regardless of the date.
• Loss harvesting (crystallising capital losses) using legitimate substitute exposure after the 30-day wash-sale window.
• Bringing forward an already-planned sale (Steve’s case) — this is the policy working as intended.
• Choosing between legacy and new-build election on a per-disposal basis under the carve-out — explicitly contemplated by Treasury.

Rule of thumb: if your motivation for the sale would survive cross-examination by an ATO investigator — “I was always going to sell within X years anyway and the reform brought it forward by Y months” — you’re fine. If the only reason for the transaction is tax, and there’s no genuine commercial substance, you’re at risk.

Decision summary table

Your situation	Should you accelerate?
Already planning to sell in 12–24 months	Consider — run the numbers, the saving is usually real but modest
Long-term hold (5+ years), broad portfolio	No — wash-selling destroys value
High-MTR (45%) + large unrealised gains	Maybe — depends on planned hold horizon; usually no for long holds
Low-MTR retiree (will face 30% min later)	Often yes — the cleanest case in the cohort
Small business owner near 15-year exemption	No — Subdivision 152-B is preserved, wait for age 55+
Crypto holder with imminent sale plans (12 mo)	Consider — large legacy share + concrete sale plan = positive math
Crypto holder with no sale plans	No — volatility dwarfs reform impact
Inherited asset planned to sell within 2-year window	No — main residence exemption auto-applies via deceased-estate concession
Asset transaction costs > 1% of value	Probably no — friction eats the tax saving
Asset has carve-out (new build, main residence)	No — carve-out already preserves favourable treatment
Slow-growth asset (real return < 2.5%/yr)	No — indexation likely shelters more than 50% discount would have
Sale already planned for 2027 calendar year	Yes if before 30 June 2027 — free upside, no extra friction
Sale planned for 2028+ but uncertain	Run the calculator — depends on growth, MTR trajectory, friction

The framework collapses to a simple question: was this sale going to happen within the next 1–2 years anyway? If yes, 30 June 2027 is a useful deadline. If no, holding almost always wins.

EOFY actions for the next 14 months

If you’ve worked through the framework and concluded “consider accelerating”:

1. Get an independent valuation of your major assets as at May–June 2026 — establishes the legacy-bucket value for Bucket B holders, and confirms your gain estimate for accelerate decisions.
2. Run the numbers in the CGT Scenario Compare tool with realistic assumptions for growth, marginal rate, and disposal date. Model multiple scenarios (accelerate vs hold 2 yrs vs hold 5 yrs).
3. Crystallise capital losses in 2026–27 regardless of which direction you decide on. Loss harvesting is a free option — the losses carry forward indefinitely and retain full offset value under the new rules.
4. Book your conveyancer / broker early for any major asset sale planned for May–June 2027. Settlement and contract dates will be congested.
5. Confirm any small-business CGT-concession eligibility with your tax agent before considering acceleration on an active asset. The 15-year, 50% active asset, retirement, and rollover concessions are all preserved — the reform doesn’t change them.
6. Document your decision rationale. If you accelerate, keep a contemporaneous note explaining why (the planned sale was already imminent, the math, the tax-and-non-tax factors). Protects you in any future ATO review of pre-reform sales.

If you’ve concluded “hold”:

1. Stop worrying about it. The single biggest mistake investors make in policy-transition windows is letting the tax tail wag the investment dog.
2. Use 2026–27 to harvest capital losses as above. This is the year to clean up under-performers.
3. Re-run your portfolio plan with the new rules in mind for long-term scenarios — the reform doesn’t change much for slow-grow defensive assets, but high-growth equity and crypto positions have a slightly different exit math now.
4. Watch the new-build carve-out if you’re a property investor considering future purchases — post-2027 new builds retain the 50% discount under the per-disposal election, which materially shifts the new-vs-existing comparison.

Sources

• Treasury Budget Paper No. 2, Tax Reform — Boosting Home Ownership measure (p.21), 12 May 2026.
• Treasury fact sheet: Negative Gearing and Capital Gains Tax Reform (12 May 2026).
• Treasury Budget Paper No. 1, Statement 4: Tax reform for workers, businesses and future generations (12 May 2026).
• ATO transitional guidance on contract-vs-settlement timing and integrity rules (forthcoming PCG, expected mid-2027).
• Master article: 50% CGT Discount Reform: Cost Base Indexation + 30% Minimum Tax from 1 July 2027.

Asset-class deep dives

The accelerate-or-hold decision plays out differently by asset class. Five companion articles walk through the worked examples and asset-specific complications:

• CGT Reform for Property Investors — investment property, main-residence carve-out, new-build 15-year exemption, depreciation cost-base interactions.
• CGT Reform for ASX Share Investors — parcel methods, DRP cost-base proliferation, ESS shares, off-market buybacks.
• CGT Reform for ETFs and Managed Funds — AMIT cost-base adjustments, distributed capital gains, FIF interaction for foreign-asset ETFs.
• CGT Reform for Crypto — Bitcoin/ETH/altcoin parcel matching, hard forks, staking rewards, stablecoin churn.
• Small Business CGT Concessions After 2027 — what’s retained: 15-year exemption, 50% active asset reduction, retirement exemption, rollover relief.

Related reading

• Negative Gearing Reform Budget 2026: What Changed by Purchase Date — paired property reform.
• 50% CGT Discount Under Review: Senate Inquiry Update — pre-Budget context and confirmed outcome.
• Budget 2026 Explained: Winners and Losers — full Budget breakdown.
• How Budget 2026 Changes Your EOFY Plan — combined EOFY 2026 and 2027 implications.