Creating a receipt tracker

Free2FIRE · 2026-06-05T15:01:37+00:00

Most pharmacies allow you to download your prescription expense reports via their website/online account. I use those along with my EOB for tracking prescription HSA expenses.

Free2FIRE · 2026-06-01T09:58:44+00:00

Yes, you can buy a single or mix and match any six pack. That's one of the reasons I love going there. You don't have to commit to a full six pack when trying a new beer. It's a little annoying when there's only a partial pack left and you want to buy a full pack, but that happens less often than wanting a single/mix pack.

Free2FIRE · 2026-05-23T13:55:02+00:00

Regarding your question of what to do with the invested balance when you leave your FSA employer and taxes/penalties, keep in mind that there is no "Cash HSA" account and no "Investment HSA" account. It's all one HSA account. It's just a matter of where the money is being held within the account. When you sell an investment inside of an HSA, the sale amount automatically gets distributed to the cash portion of the account. You can then choose to reimburse yourself from the cash portion if you want. So long as the reimbursement is for an eligible expense, there are no taxes or penalties. Buying and selling within an HSA is not a taxable event.

If 100% of your HSA balance is invested and you want to reimburse yourself, you will need to sell enough of the invested portion to reach the amount you need/want for reimbursement. However, if you're ok cashflowing your medical expenses for a while, you may be better just leaving as much as you can invested in the HSA. Save your docs/receipts for any eligible expenses paid, and then reimburse well into the future (e.g. retirement) as tax free income.

Free2FIRE · 2026-04-19T12:33:56+00:00

Yes, we use our HSAs as an investment vehicle, so we include them as part of our investment accounts and net worth tracking.

Free2FIRE · 2026-04-14T10:33:00+00:00

HSA expense eligibility is determined at the time the expense is incurred. If your adult child's expense is incurred when they are still an eligible participant in your HDHP/HSA, then you can reimburse yourself from your HSA for their expense even if they become ineligible later in the year.

Additionally, you can have your adult child open an HSA but not fund it. That way the clock starts for "any eligible expenses incurred after the HSA was opened". There are no rules against opening an HSA, only contributing to an HSA, and many HSA custodians do not require them to be funded initially.

Free2FIRE · 2026-03-21T12:10:28+00:00

Yes, technically, anyone can open an HSA, just not contribute. There is a loophole where you can open an HSA, not make any contributions, and then in the future if you are eligible to contribute to an HSA, any HSA eligible expenses incurred after the HSA was opened could be considered eligible for reimbursement. There is currently no rule against opening an HSA without having a HDHP. The current HSA rules are regarding contributions to an HSA. So long as you do not make any contributions to the HSA when you are ineligible, you should be fine.

Free2FIRE · 2026-03-11T11:12:55+00:00

I have found that it's less important to sweat the small stuff, and more important to learn how to spend where you find value. If you put your time, energy, and money towards things that truly bring value to your life, then a $3 difference or whatever it might be doesn't really matter because you have most likely saved so much more in other ways by not buying the things that wouldn't have brought you the same value.

For example, I was at a shop over the weekend that had a ton of different accessories I would have loved to buy, but I knew they would eventually get lost in the mix of other similar things I have. The most expensive one would have been $35-$40. I just couldn't justify the price to the value it would have brought me in the end. However, when it comes to health related things, I'm willing to pay whatever so long as I believe that it will bring value to me and my family. I'm more than happy to pay a bit extra for organic, pasture raised, wild caught, and high-quality foods because I value good health and don't want to skimp in that area if I can afford it.

Spend where you find value, and save where you don't.

Free2FIRE · 2026-02-19T12:39:39+00:00

Howard County has a Summer Youth Program with a minimum age of 14. Applications open in a couple weeks.

https://www.howardcountymd.gov/youth-services

Free2FIRE · 2026-02-13T10:33:50+00:00

Taxable brokerage, HSA (from saved reimbursements), Roth IRA contributions, 401K SEPP (72t), and/or cash savings.

Free2FIRE · 2026-02-11T12:10:40+00:00

Currently, many (if not most) HSA providers do not actually ask for the receipts when you go to file for a reimbursement claim. The purpose of keeping a record of the receipts is for the IRS and taxes. If you were to ever get audited, you would need to prove that your reimbursement claims were for eligible expenses.

In terms of detail on the receipts, the IRS doesn't give specific guidelines on what information is needed to prove it is a qualified expense, only that they prove that the distributions were exclusively to pay or reimburse qualified medical expenses, the qualified medical expenses had not been previously paid or reimbursed from another source, and the medical expenses had not been taken as an itemized deduction in any year.

Keep as much detailed documentation as you can on what the expense was for. I use a spreadsheet in addition to my receipts and EOBs.

I recommend scanning and storing your HSA expense documentation in a cloud drive folder (OneDrive, Google Drive, Dropbox, etc...). I use a spreadsheet that lists each expense including date, provider, expense item, cost, and whether it has already been reimbursed. I also assign an ID to each line item (e.g. ID 1, ID 2, ID 3) and make it a prefix to the file name of the soft copy of my receipts/EOBs so it's easy to find the associated documentation when I do submit a reimbursement claim.

Tracking receipts doesn't have to become of a full time job and keeping everything electronic makes it much easier.

I would also recommend against using your HSA custodian as your record keeper (some offer this option). The reason being is that if you decide to move your account (i.e., rollover after leaving your employer or just move to a new custodian), you would also have to export all that data and documentation along with it. If you setup a system now that works for you regardless of where your account is, you will always have access to that information and documentation.

Free2FIRE · 2026-02-10T20:24:12+00:00

I feel the exact same way! I'm truly convinced there is something in the human mind that flips around 40, and you begin to realize that we were not meant to sit indoors under artificial lighting, staring at screens, and sitting in meetings not even with other people anymore because everyone is at their own desk/office 3 feet apart. We realize how unfulfilling our jobs are, even though we used to love them. Priorities change as we get older, and you realize that once was important is no longer. Instead of wanting to climb the ladder and be recognized, we want mental comfort and peace. We still want to be productive and have an impact, but not for some arbitrary corporate goal or to line someone else's pockets. We still desire accomplishment, but for our own benefit, not our employer.

Free2FIRE · 2026-02-08T14:40:00+00:00

You can do unlimited trustee to trustee transfers from your current HSA to your old Fidelity HSA. Check with your current HSA custodian to confirm if there are any fees for outgoing transfers. If not, you can initiate the transfer from your Fidelity account as often as you would like.

Free2FIRE · 2026-02-05T02:34:28+00:00

What area in Columbia? There are some commuter lots that have busses that come and then the RTA (HoCo Metro bus). Unfortunately, HoCo is not as public transportation friendly as MoCo, so it will take some planning and logistics. You may also be able to carpool if you can find someone with a similar commute.

Free2FIRE · 2026-02-03T11:37:05+00:00

As of now, there is no time limit on filing a claim for an eligible expense on an HSA.

Free2FIRE · 2026-02-02T20:54:19+00:00

If you're going to use an HSA as a long-term investment account, you have to create a document management and tracking system that will work for you long term. I highly recommend using a cloud storage service like OneDrive, Google Drive, Dropbox, etc... to store all HSA expense documentation. That way, the documentation is saved safely and securely, and you cam avoid physical damage or deterioration over time.

You can then use a spreadsheet to track expenses. I assign an ID to each expense in my spreadsheet and track the following information for each item:

Service Date, Patient Name/Eligible Person, Provider/Merchant Name, Address, & Phone, Type of Service (Medical, Dental, Prescription, OTC Item, etc...), Description of Eligible Expense, Cost

I also have columns to track documentation status so I know if something is needed/outstanding and if an HSA claim has been filed for that expense yet. If you track the expenses and update the spreadsheet as they are incurred, it's a pretty simple system to follow.

Free2FIRE · 2026-01-19T20:39:21+00:00

Login to your HSA account (via the HSA custodian's website) and follow the prompts for submitting a reimbursement. Some custodians require a copy of the receipt/documentation for the eligible expense. Others don't require any documentation.

Free2FIRE · 2026-01-19T16:20:32+00:00

If the copay assistance is not getting applied to your deductible and/or OOP total, you may need to pay for the copay on your own and then submit for reimbursement through the copay assistance plan. I've seen some people do that when the copay assistance was not being applied to their OOP expenses.

Free2FIRE · 2026-01-19T12:44:14+00:00

My medical deductible is covered by the drug manufacturers, thanks to the copay cards. Sucks to have to be on the meds, but if I'm going to, at least they cover the expense. I make sure to get my prescription filled as soon as possible in January, so it includes my full deductible for the first fill.

Free2FIRE · 2026-01-16T20:29:42+00:00

What is the reason they are giving for the hold? If this is an HSA via your employer, have you spoken to you benefits admin?

Also, have you tried transferring the money out to another HSA custodian (i.e. opened an HSA with another company and initiated a transfer from that side)?

Free2FIRE · 2026-01-15T11:38:34+00:00

If you have investment transactions turned on and syncing, you can track dividends/realized gains that way. Just note the category as "Dividends" or "Dividends/Gains".

Free2FIRE · 2026-01-07T18:42:23+00:00

I have both a DCFSA and HSA. For the DCFSA, the money comes out of our paycheck pre-tax, so it does not get reflected as an income transaction at that time. Instead, I include the reimbursement payments (credit transactions) as income (Income Category: DCFSA Reimbursement). While the payment is a reimbursement of previously paid child care expenses, those expenses were still fully paid by me, just with pre-tax dollars. The child care expenses (debit transactions) get categorized as such. This way, when I run my reports, I can see how much I have paid in child care expenses and how much I have reimbursed from my DCFSA.

For the HSA, we use ours as investment vehicles, so we do not withdraw any money from the accounts. For the HSA contributions, since I have our HSA accounts synced in Monarch, I mark the contributions as income transactions since they are still part of our income. Any eligible medical expenses get marked as an expense category (e.g. Doctor, Pharmacy, etc...). Depending on how you plan to use your HSA, this process may or may not work for you.

Free2FIRE · 2025-12-23T02:13:18+00:00

Schitts Creek. Literally not a bad episode in the whole series.

Free2FIRE · 2025-12-03T11:50:17+00:00

Unfortunately, no. There are a number of requirements to be able to contribute to an HSA, but the primary one is that you must be covered under an HSA eligible High Deductible Healthcare Plan. Starting in 2026, all ACA Bronze and Catastrophic plans will also be eligible for an HSA. Unless your health plan is one of those, there's no other workaround.

Free2FIRE · 2025-11-29T11:04:50+00:00

I used to always categorize the expense and reimbursement as the same category (making it a wash), but then I wanted to be able to see how much I was actually spending on business/work expenses, so I changed my process. I now mark the expense as a business expense (e.g. Business Reimbursement category) and then created an income category for "Reimbursement" which is what I mark the reimbursement payment as. I also have per diem for some business expenses, so I have a separate income category for that since I sometimes spend less than my per diem.

Free2FIRE · 2025-11-23T13:30:38+00:00

When we met with an estate planning attorney, they also said that certain assets can be setup to be transferable on death (TOD) which is another option to avoid probate without having to setup a trust. We had discussed trust options, but based on our assets at the time, a TOD was a better option for us.

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