Sounds overly complicated to me to be honest.

I always try to follow the money....The XIn transactions from your paycheck sound like they're being handled correctly. Have you tried adding in your own company match number to your paycheck transaction so that an additional XIn for the match will also be added to each paycheck. The fact that it doesn't show up in your paycheck anywhere is unfortunate, but you can still track it in Quicken.

When sort of transactions are downloaded from Fidelity when you do a one step update? You should get two purchase transactions for each of the securities you own, one for the money that that was from your contribution and one from the company match funds. When all of these are accepted, your available cash in the account should be $0.

My company also uses Fidelity and I've been doing it this way for years. Our paychecks show the company match at each pay period on the paystub as well as a YTD total.

Mark
CF Home Fool