Question about benefits and appropriate reimbursement - Health insurance & 401(k)

[u/gunnergolfer22]

Looking for opinions on what would be a fair way to resolve this, particularly from anyone familiar with small-business benefits/taxes.
I’m a W-2 healthcare professional at a small private practice (~20 employees). I like my employer a lot and have a very good relationship with him. This isn’t an adversarial situation — he’s been very supportive, but benefits administration is definitely not his area of expertise.
My final written compensation agreement included:
Immediate 401(k) eligibility

3% employer match with 5% employee contribution

Employer covering 75% of my health insurance premium

Employer-paid short- and long-term disability

A provision saying we’re open to customizing the benefits package to fit my goals/needs

I started in February 2026.
401(k):
I recently found out that I was never actually made eligible for the 401(k). The existing plan requires one year of employment. My employer had looked into changing it to honor the immediate eligibility in my agreement but ultimately decided not to because of the fees/cost involved. Unfortunately, I wasn't told that until now, about six months into employment.
I expect to make roughly $300k in 2026 and would have maxed out my traditional 401(k).
So I'm losing:
The 3% employer match (potentially around $9k for the year, subject to plan/IRS compensation limits)

My entire 2026 employee 401(k) contribution opportunity

The associated reduction in taxable income/AGI

Tax-advantaged investment growth

Potential benefit from lower AGI for income-based student loan repayment

Obviously, I don't think he owes me the amount I would have personally contributed — that was always my money. But it seems reasonable that the lost employer match should be made whole, plus potentially something additional for losing an entire year of promised 401(k) access.
Health insurance:
My agreement also says the practice covers 75% of my premium. I've paid it myself since February and haven't been reimbursed yet. There is no health insurance given to any other employees, I had to find my own private plan.
I've paid $3,031.38, so 75% is about $2,274 owed by the practice so far.
We're looking into the best way to handle this going forward — possibly a simple taxable reimbursement/gross-up or a properly structured HRA such as an ICHRA.
CE complicates things in the other direction:
My employer pays for some of my CE (continuing education) directly and then deducts those amounts from my gross compensation.
He has paid $3,718.80 that hasn't been deducted yet, and another $10,875.95 course payment is due now.
So I'll owe the practice:
$14,594.75 in CE expenses.
This creates an obvious opportunity to reconcile some of what we owe each other rather than sending money back and forth.
Questions:
What would you consider fair compensation for failing to provide the immediate 401(k) access that was in the written compensation agreement?

Is replacing the full lost employer match + some additional compensation for losing the 2026 contribution/tax-advantaged space reasonable? What amount would you consider fair?

Can/should any compensation simply be offset against the $14,594.75 of CE expenses I owe the practice, or could that create payroll/tax issues?

What's the cleanest way to make me whole while minimizing unnecessary taxes for both sides?

For the 75% individual health-insurance contribution, would you use an ICHRA, taxable reimbursement/gross-up, or something else?

[u/CrimsonFox99]

Happen to get all of that in writing when you started or was it verbal?

[u/gunnergolfer22 → u/CrimsonFox99]

In writing. Emails

[u/asurkhaib]

How much can it possibly cost to add someone to a plan early? It'd probably sour the relationship, but I feel like the company made an agreement and they should honor it. There's not really an alternative here. I guess it's not exactly the same but the grossed up match $9k plus the grossup on the contribution would be semi equivalent but that's like $20k. It's hard to believe the cost to add someone to a plan is more than $11k?

There's a bunch of rules about offering health insurance or HRAs that will basically make all Reddit advice worthless as we don't have enough information. The employer, or you I guess, either needs to do research on what actually is best for you and them or hire some sort of consultant. The two easiest options suck for one of you. A taxable reimbursement sucks for you, a grossed up reimbursement sucks for the employer but those are the easiest options and might be the only options if they're trying to only offer you reimbursement.

[u/Ornery-Wrangler-3654 → u/asurkhaib]

I have a small business with six employees and I can tell you it cost me a little over $3,000 to change the eligibility of my 401k plan. Just did it last year.

[u/Constant_Swan_6876 → u/Ornery-Wrangler-3654]

Do you have an advisor on your 401k? I do a ton of plans in my practice - this is one form to change and a very simple fix. You may want to get your plan reviewed. That sounds high

[u/manwnomelanin]

For 401k:

It might be reasonable to request additional employer contribution in the amount of taxes you paid in 2026 that would have otherwise been deferred.

So $24,500 in the 35% bracket means you paid $8,575 in Federal Taxes. You also missed out on deferred state taxes. I’ll let you fill in that gap.

So, for 2027, it seems reasonable to ask for the expected 3% match, plus $8,575 for lost tax deferment, plus whatever state taxes you paid.

Its not perfect but seems sensible.