Every back-to-school season, Staples and Office Depot run a quiet little tradition that deal hunters look forward to all summer: penny deals. Certain school supplies drop to literally one cent, but only for a narrow window each week, and only while supplies last. If you learn how the calendar tends to unfold, you can walk in at the right moment instead of arriving a day late to empty shelves.
How the Penny Deal Cycle Works
Both Staples and Office Depot (which operates under the Office Max banner as well) structure their penny promotions as weekly rollouts. A small batch of products, typically basic school supplies, gets priced at one cent for a single week. The next week, a new batch rotates in. This pattern usually runs for several consecutive weeks during the back-to-school shopping window, which tends to fall in mid-to-late summer.
There is almost always a catch or two. Most stores require a rewards membership to access the penny price, and some require a qualifying purchase alongside the penny item. The rules shift from year to year, so checking the current week’s ad or the store’s rewards program terms before you make the trip is worth a few minutes of your time.
Early in the Season: Paper and Basic Supplies
The penny deal calendar typically opens with the most generic, high-volume items. Think composition notebooks, loose-leaf paper, pocket folders, and single-subject spiral notebooks. These are the products stores buy in bulk and are happy to give away at a loss to drive foot traffic early in the season.
- Composition notebooks are one of the most common early penny items at both chains
- Pocket folders (the basic two-pocket plastic or paper kind) show up frequently
- Loose-leaf filler paper, usually in 100- to 200-sheet packs, is another early staple
- Single-subject spiral notebooks often appear in the first few weeks
Stock up hard in this window. These items have no expiration date, the kids will use them every year, and they are the most reliably repriced to a penny. If you miss this stretch, you are unlikely to find a better price on paper goods anywhere else that season.
Mid-Season: Writing Instruments and Accessories
After the paper goods cycle winds down, both stores tend to rotate into writing instruments and small accessories. This window is slightly less predictable than the early paper phase, but the pattern shows up often enough to count on.
- Packs of pens, pencils, or crayons (usually basic branded packs, not premium lines)
- Pencil pouches or basic pencil cases
- Highlighters, glue sticks, and erasers in small packs
- Index card packs and small binders
The limit per transaction tends to be low in this phase, sometimes one or two items per rewards account. Bring every family member who has an account, or make separate trips if the store allows it. That said, confirm the current limit policy in the weekly ad, because stores have tightened and loosened these rules at different points.
Late Season: Odds and Ends (and Diminishing Returns)
By the final weeks of the penny deal run, the offerings get more unpredictable. You might see specialty items that did not move well at full price, or the chain might circle back to a leftover category from earlier weeks. Sometimes the late-season penny deals are genuinely useful; other times they are items most families already have plenty of.
- Dry-erase markers or colored pencils sometimes pop up late
- Ruled index cards and filler paper can make a second appearance
- Specialty folders or report covers occasionally appear as clearance-style penny items
This is the phase where it pays to keep your expectations realistic. If something useful appears, grab it. If the pickings are thin, you have not missed much because the best deals already ran earlier in the cycle.
How to Track the Weekly Deals Without Missing a Beat
The single best way to follow the penny deal calendar is to check the weekly circular for each chain at the start of every week. Both Staples and Office Depot publish their ads online and in-store, and the penny item is usually highlighted in the rewards or member savings section rather than the main ad.
A few habits that help:
- Sign up for email alerts from both chains’ rewards programs so penny deals land in your inbox automatically, links to join are below
- Follow deal communities (like FreebieShark) where members flag the penny items as soon as the weekly ad drops
- Shop early in the week, ideally the first day the deal goes live, since these items sell out fast at busy locations
- Call ahead to confirm stock if you are driving more than a few minutes out of your way
Rewards Programs: Your Ticket In
Neither chain makes you pay to join their rewards program, and membership is almost always required to unlock the penny price. Staples Rewards and Office Depot’s rewards program both offer free signup. Without an active membership linked to your account, the item will ring up at full price at the register, which can be a frustrating surprise if you did not check first.
A qualifying purchase requirement sometimes applies too. Some years a penny deal requires you to spend a minimum dollar amount in the same transaction. The threshold and rules vary, so read the fine print in the weekly ad before assuming the deal is a pure freebie.
The One Rule That Matters Most
The back-to-school penny deal season rewards shoppers who treat it like a calendar event rather than a happy accident. The biggest mistake is waiting. Paper goods and basic supplies go first, they go fast, and the window for each item is one week. Build a simple habit of checking the weekly ad every Monday or Tuesday, grab what is useful when you see it, and do not overthink the late-season offerings. That one routine will get you more free school supplies than any other strategy. If you have cracked a particularly good haul or spotted a deal we have not mentioned, let us know in the comments!
