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, read Import a month from your bank or aggregator (coming soon) first. 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 left nav (it’s under Money). You’ll see a list of payees, biggest by transaction count first.

[Screenshot: /Uncategorized page showing the Acme family’s grouped payee list with counts]

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. Click the payee name to expand the transaction list and confirm it’s what you think it is
2. Pick a category from the dropdown
3. Check “Apply to all future transactions from this payee”
4. Click Categorize all

That’s it. Every past and future Starbucks transaction now lands in Dining out automatically. Every Netflix lands in Subscriptions. The rule lives in payee-renames.csv if you ever want to edit it directly.

[Screenshot: Uncategorized page with the “Apply to all future” checkbox highlighted next to a payee row]

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

Try it: Open /Uncategorized ↗

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, apply to future. The “apply to future” rule keeps paying you back every month, so even a payee you only see twice is worth a 10-second rule.

If a merchant is genuinely ambiguous (a Costco run might be groceries OR home goods OR gas), don’t make a rule. Just categorize the individual transactions and skip the checkbox. You can always make a rule later.

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

Whatever’s left should be one-off transactions — the dentist, that Amazon return, your cousin’s Venmo payment. Categorize them one by one, no rules needed.

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. Click the transaction, then Split. Enter the two amounts. Categorize each piece independently.

[Screenshot: split transaction dialog with two rows for groceries and gas]

Refunds. A return of $40 to Target. Categorize it the same as the original purchase, just with a negative amount. GlidePath nets them 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.

Where to next

• Find a transaction you remember but can’t see — coming soon — search and filter on /Transactions
• Monthly close in 10 minutes — coming soon — the ritual that keeps everything fresh
• Recurring patterns and subscriptions — coming soon — automated detection of repeating charges

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.
• The “apply to future” rule is per-payee, not per-category. If a payee should sometimes go to Groceries and sometimes to Home Goods, leave the rule off and categorize each one.
• 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.