Yes. The bot is configured to ask about employer stock holdings in the 401(k) as one of the first three questions, before any rollover suggestion. Low-basis employer stock with significant unrealized appreciation triggers the NUA conversation automatically. This is the single most important operational behaviour for a rollover bot because rolling NUA-eligible stock to an IRA forfeits the long-term capital gain treatment forever.

Yes. The bot covers the NUA framework - take employer stock in-kind to a taxable brokerage in a lump-sum distribution year, pay ordinary income on the cost basis at distribution, hold for long-term capital gain treatment on the appreciation when sold. It will not recommend whether NUA is the right move because that depends on the prospect's full tax picture, other retirement income, and the basis-to-current-value ratio. The CFP handles the recommendation.

Yes. Roth 401(k) balances roll to a Roth IRA; pre-tax 401(k) balances roll to a Traditional IRA; the employer match is almost always pre-tax even in a Roth 401(k). The bot captures the Roth and pre-tax split early so the rollover paperwork is correct and the prospect doesn't accidentally consolidate Roth and pre-tax in the same destination account, which would trigger a tax mess.

Yes. The bot flags the pro-rata aggregation rule when a prospect mentions backdoor Roth contributions or non-deductible Traditional IRA contributions. Once any pre-tax IRA balance exists at year-end, every backdoor Roth conversion is taxed pro-rata. The bot routes those prospects to the CFP before the rollover lands in a Traditional IRA and breaks future backdoor Roth strategy.

The bot captures the prospect's age and the separation-from-service status, and surfaces the rule-of-55 exception for prospects age 55+ who separated from service in the year they turn 55 or later. The rule-of-55 allows penalty-free withdrawals from the prior employer's 401(k) but is lost the moment the balance rolls to an IRA. That's a counter-rollover argument the bot raises explicitly.

Yes, at the framing level. The bot covers the trade-offs between immediate Roth conversion, partial-year conversions, and conversion ladders in early retirement years. It will not recommend a conversion size, because that depends on the prospect's tax bracket projection, future income, and Medicare IRMAA thresholds. The CFP runs that modelling on the discovery call.

Yes. Pension lump-sum vs annuity is its own analysis - the bot covers the present value math at a high level, the survivor benefit question, the PBGC insurance limits, and the company-financial-health question. It captures the lump-sum offer details and the annuity options before the meeting, then routes to the CFP who runs the actuarial analysis for the recommendation.

The bot does not handle the actual rollover paperwork - that is the CFP's job during the engagement, with custodian forms, plan administrator coordination, and trustee-to-trustee transfers. The bot's job is to make sure the rollover is initiated correctly and that any NUA, rule-of-55, or Roth split considerations are surfaced before any action is taken. Initiating a rollover with the wrong destination or method is a hard-to-fix mistake.