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I have two concrete examples that I'm curious as to how people would account for them.

note that I live in Germany so so rules might be different elsewhere

Mandatory Health Insurance Benefit

At the moment I am part of a private pension scheme in Germany. I pay 750EUR/month direct debit from my bank account. I file this under Expenses:Living:Health Insurance. My employer reimburses me for 50% of that.

On my payslip I receive 375EUR/month on my pay slip. This goes to my current account. I believe the the right way to account this would be to have one side of the line item be in Income:Employer:Benefits rather than a negative line item in Expenses:Living:Health Insurance.

Yearly Health Benefit

I get 300EUR per year to purchase equipment in the purpose of improving my health. I only receive this money if I file an expense claim. So I could purchase some weights and file that under Expenses:Living:Personal Health and when I get reimbursed I have the same two options like my Health Insurance premium.

Objective

I care about how I account for this because want to be disciplined about my spending. I need to know how much I spend regardless of the benefits of my employer.

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I think there's a difference between an expense and a payment you expect to be reimbursed. Personally, I would just register a negative expense, but if you want to track it more precisely,

                                              Increase     Decrease
Income:Gross Income                                           $2000
Asset:Bank account                               $1250
Expenses:Living:Health Insurance                  $350
Accounts Receivable:Employer HI reimbursement     $350

Your actual expense is $350; the other $350 is money your employer owes you. When they reimburse you, you can record this as

                                              Increase     Decrease

Accounts Receivable:Employer HI reimbursement                  $350
Asset:Bank account                                $350

Should something happen that you don't get reimbursed, you can turn the expected reimbursement into an expense:

                                              Increase     Decrease
Accounts Receivable:Employer HI reimbursement                  $350
Expenses:Living:Health Insurance                  $350

The health benefit is handled a little differently, because it involves an active payment by your, rather than just a deduction from your paycheck.

At the beginning of each year, you can treat your remaining balance as an asset.

                                              Increase     Decrease
Equity:Health Benefit                                          $300
Asset:Health Benefit                              $300

When you buy something, record it as a regular expense.

                                              Increase     Decrease
Bank account                                                   $100
Expenses:Living:Personal Health                   $100

When you do get reimbursed, decrease your health benefit asset instead of recording a negative expense.

                                              Increase     Decrease
Asset:Health Benefit                                           $100
Bank account                                      $100

Optionally, record that $100 as income, deducted from the equity. (I'm not entirely sure I'm using the equity account correctly, but it seems to me a reasonable way to handle a potential asset, as opposed to a tangible asset.)

                                              Increase     Decrease
Income:Health Benefit                                          $100
Equity:                                            $100

At the end of the year, simply write off any unused amount.

                                              Increase     Decrease
Asset:Health Benefit                                           $200
Equity:Health Benefit                             $200
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    Thanks! For the Health Insurance, an important piece is that these transactions happen separately. I pay my HI near the beginning of the month and I get paid near the end of the month. I recently went on unpaid leave and had to pay the entire HI premium without reimbursement. I totally dig your way of thinking with the Health Benefit.
    – Scott Muc
    Aug 26, 2020 at 17:01

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