How do watched folders work?

Pick a folder. Anything that lands in it becomes a note. That’s the whole feature.

It exists for the job nobody enjoys: a stack of paper, a scanner, and an evening spent dragging files into an app one at a time. Point Harbor at the folder your scanner writes to, scan the stack, walk away. The notes are waiting for you — filed in the right notebook, tagged, and searchable by the words inside them.

For a one-off pile that’s already on your computer, you don’t need a watched folder at all: drag the files onto a notebook and each one becomes its own note.

Two kinds of folder, and the difference matters

A folder on this Mac or this PC. The Harbor app on that computer does the watching, so files are imported while the app is running. The watch belongs to that one computer — it isn’t synced to your other devices, and setting one up on your Mac doesn’t create one on your phone.

A folder in Google Drive or Dropbox. Harbor’s servers do the watching, so files are imported whether or not you’re signed in anywhere — app closed, laptop shut, phone in a drawer. Connect the service once under Settings → Connections and it keeps going on its own.

If you want imports to happen unattended, use a Drive or Dropbox folder. Most scanners can save straight into one, and it’s the setup that keeps working when you forget about it.

Where to find it, and what each app can watch

Look under Settings → Watched folders. What you can watch depends on the app:

• Mac and Windows — local folders and Google Drive and Dropbox folders.
• Web, iPhone, iPad, and Android — Google Drive and Dropbox folders only. A browser can’t watch a folder on your disk, and phones don’t really have that kind of folder, so there’s no local option on those four.
• The harbor CLI — no watched-folder commands at all.

A folder you set up in one place shows up everywhere, as long as it’s a Drive or Dropbox folder — those live with your account. Local folders stay on the computer that owns them.

Setting one up

1. Go to Settings → Watched folders and choose Connect a folder.
2. Pick where the folder is — This Mac (or this PC), Google Drive, or Dropbox.
3. Choose the folder itself.
4. Choose the notebook imported notes are filed in, and any tags to apply to every one of them.
5. Decide whether Harbor should guess the notebook from the file’s contents and move each file to the notebook it fits. With it on, the notebook from step 4 is where files land first, and where they stay when nothing fits.
6. Decide whether the original file is deleted after it’s uploaded.
7. Decide whether Harbor should suggest a title from the file’s contents, or leave each note named after its file.
8. Turn Watching on.

A new folder starts paused, and that’s deliberate. Turning Watching on is also what tells Harbor to sweep up the files already sitting in the folder — so if it started watching the moment you picked it, a folder with two hundred old scans in it would empty itself into your default notebook before you’d chosen anything. Configure first, then switch it on.

If Google shows you a warning about an unverified app while you’re connecting Drive, that’s Google’s screen rather than a fault in Harbor. Reading files out of a folder is a permission Google reviews carefully, and that review runs on its own timeline. You can continue past the warning to finish connecting, or stop there and use a Dropbox folder or a local folder instead — they do the same job. Nothing about how watched folders behave changes either way. Here’s why the warning appears, and a step-by-step walkthrough.

What gets imported

Images and PDFs, from the top level of the folder only. Subfolders are never followed. Anything else — a spreadsheet, a .docx, a zip — is left alone.

Each file becomes one note with the file embedded in it, and the note is named after the file. A scanner that produces scan_0042.pdf gives you a note called scan_0042.pdf. You can fix that one note at a time by clearing the title and pressing Suggest title, or have the folder do it for every file — see Suggest a title from the file’s contents below.

Every import goes through OCR, so the words inside the scan are searchable a little while after it arrives, and search highlights the match on the page.

Two ceilings worth knowing about. Files over 50 MB are skipped from a Drive or Dropbox folder rather than imported. And a watched folder is held to the same limits as everything else — if your account is at its note cap, imports stop and the folder tells you so, rather than quietly growing past the limit.

“Delete the file after it’s uploaded”

Off unless you turn it on. Once Harbor confirms the import, the file goes to the trash, so a mistake here is fixable:

• Google Drive and Dropbox — the file goes to the service’s own trash. Drive’s trash and Dropbox’s deleted files both keep it for a while.
• A folder on your Mac or PC — the file goes to the Trash on a Mac, or the Recycle Bin on Windows. If the drive it’s on doesn’t have one, the file stays in the folder and Harbor tells you. On a Mac, that’s from Harbor 1.0.65. Older versions delete the file outright.

Leave it off and the file stays where it is. Harbor marks it as done, so it’s never imported a second time.

“Suggest a title from the file’s contents”

Off unless you turn it on. Turn it on and Harbor names each imported note from what’s on the page instead of after the file — so a folder of scans stops being a wall of scan_0042.pdf and starts being a list of documents you recognize.

Yes, this uses AI — and it’s one of two places Harbor sends your note text to an AI without you pressing a button. The other is the notebook guess, below. The words OCR read off the page — up to the first 8,000 characters — go to OpenAI, which hands back a title. It’s the same mechanism as the Suggest title button, pointed at a folder instead of a note. It happens only for files imported by a folder you switched this on for, never for anything else in your library, and never for an encrypted note. Leave the switch off and nothing is sent. Either way, nothing you write becomes training data — see the privacy policy.

The note appears with its filename first and renames itself a few moments later. That’s the one thing worth knowing before you switch it on, because otherwise it reads like a bug. Harbor can’t name a scan until it has read the words on the page, and reading them takes a little while — so the import never waits for it. The note lands immediately under its filename, and the title changes under you once the reading is done.

It never overwrites a title you wrote. If you open the note and name it yourself in that gap, yours wins and Harbor leaves it alone. Same if another one of your devices renames it first.

It’s on every plan, free included. There’s nothing to upgrade and nothing extra to pay.

Harbor names up to 100 notes a day this way from Google Drive and Dropbox folders. Past that the files still import and keep their filenames, and you get one email — one a day, not one per file — saying today’s are used up. It resets each day. It’s a guardrail on a job that costs us money to do, not a nudge to buy anything.

Encrypted notes never get a suggested title. Mostly the question doesn’t come up, because a watched folder can’t file into a notebook that encrypts by default in the first place — Harbor won’t let you choose one, for the reason in Two limits below. The exception is a local folder on your Mac or PC, which holds your key and so can encrypt on the way in. Those notes keep their filenames: once a note is encrypted, our servers hold only ciphertext and there is nothing left to read. That’s the encryption trade-off again, not a fault.

In a Google Drive or Dropbox folder, a file with no readable text just keeps its filename. A photo of a beach has nothing to name a note after. Nothing fails and nothing is reported — you get the filename, which is what you’d have had anyway.

A folder on your Mac or PC can title from the picture. It asks for a title the same way the Suggest title button does, so a file with no text yet — a photo, or a scan OCR hasn’t finished reading — can get a title from what the picture shows, and a copy of the picture goes to OpenAI. Those count toward the button’s daily limit on picture titles.

On a folder on your Mac or PC, the Harbor app does the asking. Our servers don’t rename those notes on their own schedule, so the switch needs Harbor running, and online, for a couple of minutes after it imports the file. Quit in that window and the note keeps its filename — clear the title, press Suggest title, and you’re back where you’d have been.

“Guess the notebook from the file’s contents”

Off unless you turn it on. Turn it on and Harbor reads each file the folder imports and moves it to the notebook it fits best. The water bill goes to Utilities, the report card to School, and you don’t sort a thing.

The note lands in the folder’s own notebook first, and moves a few moments later. Harbor can’t tell where a scan belongs until OCR has read it, so the import doesn’t wait. Once the words are in, the note moves. If no notebook fits well, it stays where it landed. A file with no readable text stays put too, because there’s nothing to guess from.

Your move wins. Move the note yourself before Harbor gets to it, here or on another device, and Harbor leaves it alone.

Yes, this uses AI too, and it goes to a different company. To guess, Harbor sends TypeSafe the file’s OCR text (up to the first 8,000 characters), the file’s name, the names and stacks of your notebooks, and up to 15 recent note titles from each notebook. That’s how it learns what each notebook holds. It happens only for files imported by a folder you switched this on for. A notebook that encrypts by default is never sent and never picked, and an encrypted note’s title is never sent. TypeSafe says it doesn’t train on customer data. Who gets what, in full, is in the privacy policy.

It guesses better with a little help:

• Give notebooks clear names. “Taxes” is easy to match a scan to. “Misc 2” isn’t.
• Notebooks that already hold a few notes guess better than empty ones, because their titles show what belongs there.
• Make the folder’s own notebook a holding place, something like Inbox or Scans. Whatever Harbor can’t place waits there for you.
• It works best on English text.

It’s in the web app now, and in the Mac, iPhone, iPad, Android and Windows apps from their next update. Harbor’s servers import a Google Drive or Dropbox folder and ask for the guess themselves, so once you’ve switched it on from the web, the folder files your scans whichever app you use. A folder on your Mac or PC needs the update. Its app uploads each file, then asks for the same guess, so Harbor needs to stay running and online for a couple of minutes after it imports the file. If the folder’s notebook encrypts new notes, the switch is grayed out, because Harbor can’t read an encrypted note to guess where it goes.

More on how it decides, and how to set things up so it guesses well: Can Harbor file my scans into the right notebook?

Pause Watching to change a folder’s settings

This is the one that catches people out. While Watching is on, all of a folder’s settings — the notebook, the notebook guess, the tags, the delete toggle and the title toggle — are locked. The app grays them out and tells you to pause Watching to change them.

Turn Watching off, make the change, turn it back on. Nothing is lost — and switching it back on runs the catch-up sweep again, so anything that arrived while it was paused comes in with the settings you just chose.

The reason is unglamorous: an import already in flight must not have its destination changed underneath it, or half a stack of scans ends up in one notebook and half in another.

How quickly things show up

Drive and Dropbox folders are checked every couple of minutes. If you don’t want to wait, Check now sweeps every folder immediately.

Local folders on a Mac or PC react almost as soon as the file appears, with a brief pause first so a file that’s still being written — a scan mid-page, a large copy — is picked up once it’s finished rather than half-done.

When a folder stops working

A folder that can’t import turns red and says why: the folder was deleted or renamed at the source, the notebook it filed into is gone, or the connection to Google or Dropbox was revoked. Harbor emails you once when that happens, not once per file.

Fix the cause — reconnect the service, pick a different notebook — and it heals itself on the next sweep. Turning Watching off and on again forces the issue.

Two limits to know before you set one up

Most watched folders can’t file into a notebook that encrypts by default. A Drive or Dropbox folder is imported by Harbor’s servers, and they’d have to hold your plaintext to do it — which is exactly what encryption is designed to prevent. Harbor refuses the setup rather than quietly filing those notes unencrypted, and the notebook guess never picks one either. The one place it does work is a local folder on your Mac or PC: that import runs in the app on your machine, which holds your key, so it can encrypt on the way in. Encryption has to be unlocked for it to work — if it’s locked, the folder waits and says so, and the files import on the next sweep after you unlock.

Nothing is ever imported twice. Harbor remembers every file a folder has processed, and it recognizes an identical file dropped in again under a new name. Re-running a catch-up sweep is always safe.

What we’d actually do with it

Make a folder called Scans in Google Drive or Dropbox, point your scanner at it, and give it a notebook called Scans and a scan tag. Turn the notebook guess on, so each document moves to Taxes or Medical or wherever it belongs, and anything it can’t place waits in Scans. Turn the title suggestion on too — a stack of paper is exactly what it’s for, and filenames off a scanner are worth nothing. Leave “delete after upload” off for the first week; you’ll trust it faster if you can see the originals piling up untouched.

Then scan the drawer. The whole drawer. That’s the point of the thing: the effort per document drops to putting it face-down and pressing a button, and what comes out the other end is named, filed, tagged and searchable without you having typed a word.