How do I add expenses?

Last updated: August 21, 2026

Summary: Most of the time, contractors enter their own expenses in their portal — you don't need to do it for them. This article is for the cases where you add an expense on a contractor's behalf: from Expenses → Create Expense, pick the right assignment and expense type, and enter the amount, date, and description. The expense type you choose determines how the payment is taxed — reimbursements and qualifying travel per-diem stipends can be non-taxable, but only when they meet the rules below; bonuses are always taxable. Expenses process like timesheets, so the date decides which paycheck they land on.

Who enters expenses?

By default, contractors submit their own expenses — they'll see an Expenses area with a Create an Expense button in their portal, upload their receipt, and enter the details themselves (see the worker-facing How to submit an expense or mileage reimbursement). You'd add an expense yourself only when you're entering it on their behalf — for example, if self-entry is turned off for an assignment, or you're handling a reimbursement for them. The steps below are for that case.

How to add an expense (on a contractor's behalf)

  1. Open Expenses in the left-hand menu and click Create Expense.

  2. Choose the assignment. If the contractor has more than one assignment, pick the correct one — this matters especially when the expense will be billed to a client.

  3. Choose the expense type (see the tax rules below — this is the most important field).

  4. Enter the amount you want to pay the contractor, the date, and a description.

  5. Save.

Timing: expenses process like timesheets. For an expense to appear on this week's paycheck, date it within the previous week.

Expense types and how they're taxed

The old rule of thumb that "reimbursements and stipends aren't taxed, bonuses are" is not accurate. Taxability depends on the type and whether it meets IRS/CRA standards:

  • Reimbursements — repaying a real, documented business expense. Non-taxable when they qualify (business purpose + a category, and typically a receipt) under an accountable plan. A taxable reimbursement type also exists for amounts that don't qualify. Reimbursements require a category.

  • Travel per-diem stipends — meals/lodging support for travelers. These are only allowed on travel assignments (you'll see "Assignment does not allow stipends" otherwise) and are only non-taxable when the assignment genuinely meets temporary-travel standards: the worker has a real tax home they're traveling away from, and the assignment is expected to last under one year (Ascen caps travel at 12 months in the same metro area). If those standards aren't met — no qualifying tax home, missing eligibility documents, the assignment runs long, or the amount is out of policy versus GSA per-diem rates — the stipend must be paid as taxable instead. Stipends go through a review before approval to check exactly this.

  • Bonuses (discretionary and non-discretionary) — always taxable wages.

Which types are available also depends on the worker:

  • Independent contractors (1099/IC) don't receive W-2-style reimbursements or stipends — IC expenses are handled as the contractor's own IC expenses, not employer reimbursements.

  • Canada (T4) assignments support reimbursements only (no per-diem stipends or bonuses through this flow).

When in doubt about whether something should be taxable, choose the taxable variant or email support@ascen.com — misclassifying a taxable payment as non-taxable creates a compliance problem for the worker's W-2.

Billing the expense to the client

  • Mark the expense no bill if you don't want it invoiced to the client. Otherwise it's sent to the client for approval along with that period's pending timesheets.

  • The client sees your description when they approve the expense, so keep it clear and professional. Note, though, that the description is not the label on the final invoice: on the invoice, a billed expense appears as a line under the worker's name and job title with the type shown as "Expense." (A short, separate line-item note can be added to print on the invoice if needed.)