Categorize a month of transactions without losing your mind

Every personal-finance app eventually shows you a list of uncategorized transactions and tells you to “go through them.” Most people quit there. This walks you through how GlidePath wants you to do it — once per merchant, not once per transaction — so a typical month takes 15 minutes instead of two hours.

What you’ll learn

• Why the rules engine is your friend (and where to find it)
• How to bulk-categorize a month in three passes
• How to handle the awkward stuff: split transactions, refunds, transfers
• How to make sure next month is faster than this one

Before you start

You’ll want a month of transactions already imported. If you haven’t done that yet, bring in a month of transactions first — import a CSV from your bank, or from an aggregator (a tool like Simplifi or Monarch that pulls all your accounts into one place) — then come back here.

The thing nobody tells you

Most uncategorized transactions are from merchants you’ve seen before. Starbucks, Costco, your mortgage company, Netflix. If you categorize Starbucks once and tell GlidePath “always do this,” you never categorize Starbucks again. The whole game is categorize the merchant, not the transaction.

The Uncategorized page is built around this idea. It groups transactions by payee, sorts by frequency, and lets you assign a category to the whole group in one click.

Step 1 — Open the Uncategorized page (1 min)

Open Uncategorized from the top nav (it’s under Money). You’ll see your transactions grouped by payee, biggest groups first.

The top of the list is where to spend your time. The bottom is one-offs you’ll handle in pass three.

Step 2 — Pass one: knock out the frequent flyers (5 min)

For the top 10 payees, do this:

1. Glance at the payee’s row to confirm it’s what you think it is
2. Pick a category in the Bulk categorize column
3. Click Apply to N (the button counts the group for you — “Apply to 14”)

That’s it. Every uncategorized Starbucks row gets Dining out, and a rule is saved automatically — every future Starbucks import lands there too, no extra click. The rule lives in payee-rules.csv, and every learned rule is reviewable (and editable) on the in-app /PayeeRenames page.

After ten payees you’ve usually cleared 60-80% of the month’s transactions. That’s the leverage.

Try it: Open /Uncategorized ↗ (works when the desktop app is running on this computer — just browsing? See the demo)

Step 3 — Pass two: handle the medium-frequency stuff (5 min)

Move down the list. For payees you’ve seen 2-5 times in the month, the same flow — pick a category, click Apply to N. The learned rule keeps paying you back every month, so even a payee you only see twice is worth a 10-second pass.

If a merchant is genuinely ambiguous (a Costco run might be groceries OR home goods OR gas), think before bulk-applying — a single learned rule will guess wrong half the time. Two honest options: pick the category that fits most of that merchant’s charges and split the exceptions afterwards (next section), or let AI Categorize (an optional cloud feature — it sends each row’s merchant, amount, date, and account type plus your category names; never account names, numbers, balances, or owners) walk the rows one-by-one with a suggestion each. A bad rule is easy to fix later on /PayeeRenames, but no rule beats a wrong rule.

Step 4 — Pass three: the long tail (3 min)

Whatever’s left should be one-off payees — the dentist, that Amazon return, your cousin’s Venmo payment. They sit at the bottom as groups of one: same two clicks, just Apply to 1. (Yes, that learns a rule for the dentist too. Good — the next checkup categorizes itself.)

For the ones you genuinely don’t know what to do with, Uncategorized is a valid permanent category. Don’t force it. A few uncategorized transactions a month is normal and doesn’t break anything.

The awkward cases

Split transactions. A $200 Costco run that’s $120 groceries + $80 gas. On the Transactions page, click the split icon (⌲) on that row, enter the two amounts, and give each piece its own category. The pieces must sum to the original total — the app checks.

Refunds. A return of $40 to Target. Categorize it the same as the original purchase — the amount carries the opposite sign of the purchase (the purchase is the negative one; the refund comes back positive, exactly as your bank exports it). GlidePath nets the pair automatically in cash-flow views.

Transfers between your own accounts. Moving $500 from checking to savings is not income or expense. Use the category Transfer (it’s special-cased — the cash-flow page filters transfers out so they don’t double-count).

What just happened

You spent ~15 minutes and a month of transactions is now categorized. More importantly, next month will take half as long because every “apply to future” rule you set is now doing the work for you.

You can see this compounding in the Uncategorized page itself. Open it next month and the list should be noticeably shorter. By month four, only genuinely new merchants show up.

Ask Glide about this

Open ✨ Ask Glide and try: “What’s a reasonable number of spending categories to have?” Glide will walk you through the trade-off between too few (no signal) and too many (analysis paralysis).

Common pitfalls

• Don’t try to invent categories on the fly. Use the defaults for the first month. If something doesn’t fit, drop it in “Other” and look at the patterns later — you’ll see which custom categories you actually need.
• Learned rules are per-payee, not per-category. If a payee should sometimes go to Groceries and sometimes to Home Goods, don’t bulk-categorize it — handle those rows individually so no rule gets learned.
• Transfers are not income or expense. Always use the Transfer category for money moving between your own accounts. Otherwise your cash flow will lie to you.