Google Keep vs Apple Notes when everything just breaks

Table of Contents

1. Installing both apps on every device does not make them equal

So I had Keep and Apple Notes installed on my MacBook, iPhone, and a Pixel 7—just to see how weird things would get if both were treated as interchangeable. It did not disappoint. I copied a checklist from Notes into Keep while on iOS. Looked fine there. Then I opened the synced Keep note on Android and half the checklist formatting turned into bullets, the other half converted into plain hyphens. Not only that, but tapping any item didn’t consistently check it off—some tapped once, others needed two taps. No error messages, just silent disagreement.

Visually, they both look sane in isolation. But keep in mind:

Apple Notes only syncs seamlessly between Apple devices. Anything else, you’re on iCloud Web, which loads slowly and has brutal keyboard lag.
Google Keep’s web UI is fast but edits can mysteriously roll back if you have the tab open on multiple desktops. I lost 30 seconds of typing because my iMac sync lagged 5 seconds behind the Chromebook.
You can see the sync spiral on shared notes. One version gets semi-committed. The other sees a ghost version. There is no granularity.

The core issue is that both want to pretend they work the same everywhere. They kind of do—until timing, formatting, or emojis get involved.

2. Apple Notes share links silently expire after vague durations

I thought I was going crazy. I tapped a share link from a teammate who swore she had “just re-sent it.” It opened iCloud, spun up the Notes preview, then said nothing. Just didn’t load. Later I realized Apple had stopped honoring older Notes share links after she bumped the note’s structure—adding a table to it. That broke the old URL but didn’t revoke it.

This is the kind of quiet behavior that makes debugging near impossible unless someone notices the pattern. What’s even better: Apple Notes doesn’t notify the person who shared the note that their link is now a dud. It’ll look fine on their end. You only know something broke when three coworkers paste it into Slack and all say “The page is blank?”

There’s no official TTL, but with multiple test notes I shared, links started acting flaky after editing them with:

Multiple embedded images
Table formatting toggled on-off
Offline edits that re-synced 30+ minutes later

To fix it, she had to re-add me with an entirely fresh link—even though the share sheet showed me as still invited.

3. Pinning notes in Google Keep has a syncing order bug

Pinning is one area Google Keep thinks it’s clever. But I’ve seen multiple occasions where pinned notes sort differently across devices. If I pin a note on Android, then open the web UI within 15 seconds, the note appears last in the pin row instead of first. Refreshing sometimes fixes it, sometimes not.

This matters when you rely on visual spatial memory to grab your most frequent notes. On Tuesday morning I pinned a packing list before heading to the airport. Glanced at Keep in Chrome, started editing the second pinned note instead—thought it was the right one. Ended up nearly bringing my podcast mic instead of socks.

Aha moment: If you check the dev console (F12) in keep.google.com, toggling a pin triggers a `PATCH` with partial object arrays. But the array index position is stored client-side only. It’s not reliably part of the update payload. So if two client sessions conflict the order, their LRU positioning wins locally, not system-wide. That’s why order mismatch emerges.

4. Formatting tables in Apple Notes is unstable on older macOS versions

I’m still on Catalina on one work machine (don’t ask)—and guess what? Apple Notes tables lose column widths randomly when synced from iOS 17. On one note containing a weekly planning grid, the header row stayed aligned, but the rest squished inward when reopened on the Mac. I spent half an hour wondering if I’d tabbed wrong. Nope.

Turns out the Notes app on older macOS can accept—but not fully interpret—newer layout params sent by the iOS version of Notes. The app doesn’t crash. It just silently renders constrained spacing depending on available screen width. You see the full text when you double-click a cell, but most cell content looks cut off otherwise.

There’s no log. No alert popup. You have to notice that something “feels cramped.” I worked around it by converting the table to plain text, copying it to Bear, adjusting it there, then pasting it back. Not elegant. Very annoying in a shared note where coworkers thought I’d removed columns entirely.

5. Checkboxes break in both apps but for totally different reasons

In Google Keep:

Checkboxes seem super lightweight until you realize they have hidden state properties. Unchecking a completed item doesn’t actually move it back to the active list unless you manually drag it. Also, toggling a checkbox via voice command (e.g. through Google Assistant) doesn’t sync back the position—it just flips the check state.

In Apple Notes:

Checkboxes added inside bulleted lists create an invisible hierarchy. Deleting the bullet symbol does not delete the checkbox. It turns into a phantom checkbox that can’t be tapped but renders in the note. The only fix is to copy the entire line into TextEdit and delete it from there, then paste it back in.

One weird edge case: when you paste a block of checkboxed items from Notes into Slack, only two formats survive—plain text or Apple’s weird RTF wrapper. In the latter case, Slack renders ZERO checkboxes. Just blank lines. Totally silent failure. Very fun when trying to share a real-time to-do list in a meeting.

6. Apple Notes does not expose note creation time in the UI

I needed to confirm when I added a note about a VPN config we tested in April. The note had the modified time—May 8th—but I never touched it since. Just opened it. That changed the mod time. Turns out: Notes does not expose original created time in the native UI anywhere. You get only the last touched time.

But you can extract the original timestamp using iCloud web tools or from the Mac’s Spotlight metadata layer. I ran this Terminal command on the .note file stored in container directories:

mdls -name kMDItemFSCreationDate ~/Library/Group\ Containers/group.com.apple.notes/...

Not recommended unless you really want that metadata badly. High chance of breaking sandbox protections while poking around.

Why does this matter? I needed to prove that we scoped a feature early, and our PM was using modified date as proof it hadn’t. Only way to fix that argument was with local file metadata. Which doesn’t help if your company device has endpoint security blocking file access.

7. Google Keep search misses text inside images surprisingly often

Feel like most people don’t realize this, but Keep’s Optical Character Recognition (OCR) in images is flaky. On paper it says it can find text inside uploaded photos. In practice, it depends when you uploaded it. I have two snapshots of the same whiteboard. Uploaded both. Only the one I titled with a keyword ever shows up in search results. The other never did.

I thought the OCR hadn’t finished processing yet. Waited an hour. Still nothing. Renamed the note and then it surfaced in search immediately. I think the OCR extraction only runs once and gets tied to the note’s state at that moment. If the system fails to extract text on first pass (say image quality is low), it won’t retry unless you trigger a visible change. Renaming counts. Editing color label doesn’t.

This limitation isn’t documented anywhere. But you can test it by creating a new note, uploading a screenshot of any typed text, and searching for a unique phrase. Wait 90 seconds. If it doesn’t show—try renaming and search again. Magically appears.

I now standardize debugging OCR issues by logging note creation and title changes in a spreadsheet, then checking what surfaced. Inelegant, but at least it’s measurable.