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So the question is, should I contact Fidelity (the plan administrator) about converting the account from a Traditional 401k to a Roth 401k?

Does your plan allow for conversions while you are still employed? The law allows for it, but not all plans do.

If your plan does not allow for conversions funds already contributed, then you can only change the contributions going forward, and won't be able to do any conversions of already contributed amounts.

My AGI will likely put me in a 25% tax bracket.

If you are close to the breakpoint between the 25% and 28% brackets, be sure that the added $2000 won't put you over, or be sure that you are willing to pay at a 28% rate on some of the conversion.

By the end if the year, I will have made around $2000 in Traditional 401k contributions
the added tax liability should be no more than $500

So you've had no gains in your account? Or you are only converting the amount that you contributed, and not the gains?

I figure if I am ever to do this, before the end of the year would be cleanest from an administrative perspective.

From whose administrative perspective? If the plan allows conversions, they don't really care if the contributions were made during the same year or not - the records that they have to keep are the same in either case. And as the participant, I don't know what 'administrative' work there would be for you to do.

If you're worried about the administrative tax issues - they are based on the amount that you convert, not what year the contributions were made.

Who is also wondering if a Traditional company matching contribution is any more or less valuable than a Roth company matching contribution...

Sorry, there is no such thing as a 'Roth company match'. While the company can match the amount that you put into the 401(k) plan, the law requires all company contributions/matches be pre-tax (traditional)

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