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COBRA participants have the same OE rights as actives. Nothing about OE rights changes the standard 60-day election period or 45-day period to make the first premium payment. I'll defer to you and your COBRA TPA for the specific procedures of the distribution of materials and election process for your plan. More details: https://www.newfront.com/blog/open-enrollment-rights-for-fmla-leaves-and-cobra-participants-2 Slide summary: 2024 Newfront COBRA for Employers Guide

Part of the confusion might be that there are two different 5 year rules. The one used to determine if there is qualified Roth distribution is one clock per Roth account, even if the Roth account has separate sub-accounting (which is one of your Qs: it’s just an accounting). The clock starts with the first deferrals, in-plan Roth rollover or designated Roth employer contribution. Whichever is first starts the clock for determining if the earnings can be distributed tax-free. Separate accounting is used to determine when an amount can be distributed. For example, Roth deferrals generally can’t be distributed prior to 59 1/2 but an in-plan rollover might be distributable sooner, depending on the plan and the source of the rollover. The second 5 year rule is an anti-abuse rule relating to the 10% early tax. It’s referred to as a recapture rule. The rule only applies to in-plan Roth rollovers. Normally the 10% tax is based on the amount includible in income. Roth is after-tax so the 10% tax would only apply to earnings, if it’s not a qualified distribution. But suppose I have a pre-tax account, I want an early distribution and don’t want to owe the penalty tax. I do a Roth rollover and pay normal taxes. At a later date, I then take a distribution from that account. I don’t owe the 10% penalty on the basis. Or maybe I do. Congress plugged the possible abuse by imposing the 10% penalty on the basis if the rollover was done within a 5 year period prior to the distribution. For that rule, each in-plan Roth rollover has its own 5 year period. 2010-84 Q&A 12. I don’t see anything in SECURE 2.0 indicating that the recapture rule applies to Roth employer contributions.

The TPA I work for has different rates for positions that do the work and bill accordingly. We would most likely not bill for this kind of situation. It is penny wise pound foolish. As HarleyBabe notes they are upset already. A few hundred in revenue isn't worth making them madder. The cost to market a new client is pretty high. The cost of one lost client is higher than all the revenue you will collect billing for 10 or 15 people. I know very few management groups in the TPA world that would risk that.